Functional Oligothiophene-Based Materials: Nanoarchitectures and Applications

Handbook of Thiophene-Based Materials: Applications in Organic Electronics and Photonics

Volumn , Issue , 2009, Pages 1-155

  Mishra, Amaresh ^a   Ma, Chang Qi ^a   Segura, José L ^b   Bäuerle, Peter ^a  

^a UNIVERSITY OF ULM   (Germany)

^b UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

1D linear oligothiophenes functionalized with surface active groups; Calixarene functionalized oligothiophenes; End capped oligothiophenes (EC5T EC7T) in OLEDs; Ferrocene functionalized oligothiophenes redox functional systems; Functional oligothiophene based materials nanoarchitectures and applications; Fused thiophenes; Heteroaromatic ring fused oligothiophenes; Macrocyclic thiophenes; Thiophene based porphyrinoid macrocycles

Indexed keywords

EID: 77953899997     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470745533.ch1     Document Type: Chapter

References (518)

1. D. Fichou (ed.), Handbook of Oligo-and Polythiophenes, Wiley-VCH Verlag GmbH, Weinheim, 1999.
2. K. Müllen and G. Wegner (eds), Electronic Materials: the Oligomer Approach, Wiley-VCH Verlag GmbH, Weinheim, 1998.
3. L. B. Groenendaal, J. Friedrich, D. Freitag, H. Pielartzik and J. R. Reynolds, Poly(3,4-ethylenedioxythiophene) and its derivatives: past, present and future, Adv. Mater., 12, 481-494 (2000).
4. L. Groenendaal, G. Zotti, P. H. Aubert, S. M. Waybright and J. R. Reynolds, Electrochemistry of poly(3,4-alkylenedioxythiophene) derivatives, Adv. Mater., 15, 855-879 (2003).
5. S. Kirchmeyer and K. Reuter, Scientific importance, properties and growing applications of poly(3,4-ethylenedioxythiophene), J. Mater. Chem., 15, 2077-2088 (2005).
6. T.-A. Chen and R. D. Rieke, The first regioregular head-to-tail poly(3-hexylthiophene-2,5-diyl) and a regiorandom isopolymer: nickel versus palladium catalysis of 2(5)-bromo-5(2)-(bromozincio)-3-hexylthiophene polymerization, J. Am. Chem. Soc., 114, 10087-10088 (1992).
7. T.-A. Chen, R. A. O'Brien and R. D. Rieke, Use of highly reactive zinc leads to a new facile synthesis for polyarylenes, Macromolecules, 26, 3462-3463 (1993).
8. R. D. McCullough, R. D. Lowe, M. Jayaraman and D. L. Anderson, Synthesis and control of conducting polymer architectures: structurally homogeneous poly(3-alkylthiophenes), J. Org. Chem., 58, 904-912 (1993).
9. G. Horowitz, D. Fichou, X. Peng, Z. Xu and F. Garnier, A field-effect transistor based on conjugated α-sexithienyl, Solid State Commun., 72, 381-384 (1989).
10. F. Garnier, G. Horowitz, X. Peng and D. Fichou, An all-organic 'soft' thin film transistor with very high carrier mobility, Adv. Mater., 2, 592-594 (1990).
11. F. Geiger, M. Stoldt, H. Schweizer, P. Bauerle and E. Umbach, Electroluminescence from oligothiophene-based light-emitting devices, Adv. Mater., 5, 922-925 (1993).
12. N. Noma, T. Tsuzuki and Y. Shirota, α-Thiophene octamer as a new class of photo-active material for photoelectrical conversion, Adv. Mater., 7, 647-648 (1995).
13. F. Garnier, G. Horowitz and D. Fichou, Conjugated polymers and oligomers as active material for electronic devices, Synth. Met., 28, 705-714 (1989).
14. P. Bauerle, End-capped oligothiophenes-new model compounds for polythiophenes, Adv. Mater., 4, 102-107 (1992).
15. S. Gronowitz, Thiophene and its derivatives, in The Chemistry of Heterocyclic Compounds, ed. A. Weissberger and E. C. Taylor, John Wiley & Sons, Inc., New York, 1985-1992, Vol. 44, Parts 1-5.
16. F. Diedrich and P. J. Stang (eds), Metal Catalyzed Cross-coupling Reactions, Wiley-VCH Verlag GmbH, Weinheim, 1998 and 2006.
17. T. Yamamoto, K. Sanechika and A. Yamamoto, Preparation of thermostable and electric-conducting poly(2,5-thienylene), J. Polym. Sci, Polym. Lett. Ed., 18, 9-12 (1980).
18. G. B. Street and T. C. Clarke, Conducting polymers: a review of recent work, IBM J. Res. Dev., 25, 51-57 (1981).
19. G. Tourillon and F. Garnier, New electrochemically generated organic conducting polymers, J. Electroanal. Chem., 135, 173-178 (1982).
20. J. Roncali, Synthetic principles for bandgap control in linear π-conjugated systems, Chem. Rev., 97, 173-206 (1997).
21. J. Roncali, Advances in the molecular design of functional conjugated polymers, in Handbook of Conducting Polymers, ed. T. A. Skotheim, R. L. Elsenbaumer and J. R. Reynolds, Marcel Dekker, New York, 1998, pp. 311-341.
22. J. Roncali, Electrogenerated functional conjugated polymers as advanced electrode materials, J. Mater. Chem., 9, 1875-1893 (1999).
23. G. Zotti, Electrochemical synthesis of polyheterocycles and their applications, in Handbook of Conductive Molecules and Polymers, ed. H. S. Nalwa, John Wiley & Sons, Ltd, Chichester, 1997, Vol. 2, pp. 137-170.
24. M. Pomerantz, Low bandgap conducting polymers, in Handbook of Conducting Polymers, ed. T. A. Skotheim, R. L. Elsenbaumer and J. R. Reynolds, Marcel Dekker, New York, 1998, pp. 277-309.
25. L. M. Goldenberg, M. R. Bryce and M. C. Petty, Chemosensor devices: voltammetric molecular recognition at solid interfaces, J. Mater. Chem., 9, 1957-1974 (1999).
26. D. T. McQuade, A. E. Pullen and T. M. Swager, Conjugated polymer-based chemical sensors, Chem. Rev., 100, 2537-2574 (2000).
27. B. J. Holliday and T. M. Swager, Conducting metallopolymers: the roles of molecular architecture and redox matching, Chem. Commun., 23-36 (2005).
28. T. Izumi, S. Kobashi, K. Takimiya, Y. Aso and T. Otsubo, Synthesis and spectroscopic properties of a series of α-blocked long oligothiophenes up to the 96-mer: revaluation of effective conjugation length, J. Am. Chem. Soc., 125, 5286-5287 (2003).
29. P. Bauerle, Sulfur-containing oligomers, in Electronic Materials: the Oligomer Approach, ed. K. Müllen and G. Wegner, Wiley-VCH Verlag GmbH, Weinheim, 1998, pp. 105-197.
30. J. Roncali, Oligothienylenevinylenes as a new class of multinanometer linear π-conjugated systems for micro-and nanoelectronics, Acc. Chem. Res., 33, 147-156 (2000).
31. C. Spangler and M. He, Charge-state incorporation in dithienylpolyenes and thienylene polyenylene oligomers and polymers, in Handbook of Organic Conductive Molecules and Polymers, ed. H. S. Nalwa, John Wiley & Sons, Ltd, Chichester, 1997, Vol. 2, pp. 389-414.
32. J. M. Tour, Molecular electronics. Synthesis and testing of components, Acc. Chem. Res., 33, 791-804 (2000).
33. P. F. H. Schwab, J. R. Smith and J. Michl, Synthesis and properties of molecular rods. 2. Zig-zag rods, Chem. Rev., 105, 1197-1279 (2005).
34. J. Roncali, P. Blanchard and P. Frere, 3,4-Ethylenedioxythiophene (EDOT) as a versatile building block for advanced functional π-conjugated systems, J. Mater. Chem., 15, 1589-1610 (2005).
35. T. Ozturk, E. Ertas and O. Mert, Dithienothiophenes, Tetrahedron, 61, 11055-11077 (2005).
36. J. Hassan, M. Sevignon, C. Gozzi, E. Schulz and M. Lemaire, Aryl-aryl bond formation one century after the discovery of the Ullmann reaction, Chem. Rev., 102, 1359-1470 (2002).
37. F. J. M. Hoeben, P. Jonkheijm, E. W. Meijer and A. P. H. J. Schenning, About supramolecular assemblies of π-conjugated systems, Chem. Rev., 105, 1491-1546 (2005).
38. D. Fichou, Structural order in conjugated oligothiophenes and its implications on opto-electronic devices, J. Mater. Chem., 10, 571-588 (2000).
39. Y. Shirota, Organic materials for electronic and optoelectronic devices, J. Mater. Chem., 10, 1-25 (2000).
40. U. Mitschke and P. Bauerle, The electroluminescence of organic materials, J. Mater. Chem., 10, 1471-1507 (2000).
41. I. F. Perepichka, D. F. Perepichka, H. Meng and F. Wudl, Light emitting polythiophenes, Adv. Mater., 17, 2281-2305 (2005).
42. H. E. Katz, Z. Bao and S. L. Gilat, Synthetic chemistry for ultrapure, processable and high-mobility organic transistor semiconductors, Acc. Chem. Res., 34, 359-369 (2001).
43. Y. Sun, Y. Liu and D. B. Zhu, Advances in organic field-effect transistors, J. Mater. Chem., 15, 53-65 (2005).
44. T. Otsubo, Y. Aso and K. Takimiya, Functional oligothiophenes as advanced molecular electronic materials, J. Mater. Chem., 12, 2565-2575 (2002).
45. 60-fullerene as molecular heterojunctions for organic photovoltaics, Chem. Soc. Rev., 34, 483-495 (2005).
46. 60/π-conjugated oligomer approach, Chem. Soc. Rev., 34, 31-47 (2005).
47. G. Barbarella, M. Melucci and G. Sotgiu, The versatile thiophene: an overview of recent research on thiophene-based materials, Adv. Mater., 17, 1581-1593 (2005).
48. S. K. Collins and M. P. Vachon, Unlocking the potential of thiaheterohelicenes: chemical synthesis as the key, Org. Biomol. Chem., 4, 2518-2524 (2006).
49. S. Hotta, Molecular conductive materials: polythiophenes and oligothiophenes, in Handbook of Organic Conductive Molecules and Polymers, ed. H. S. Nalwa, John Wiley & Sons, Ltd, Chichester, 1997, Vol. 2, Chapter 8, pp. 309-387.
50. T. Otsubo, Y. Aso and K. Takimiya, Synthesis, optical and conductive properties of long oligothiophenes and their utilization as molecular wires, Bull. Chem. Soc. Jpn., 74, 1789-1801 (2001).
51. F. Garnier, R. Hajlaoui, A. Yassar and P. Srivastava, All-polymer field-effect transistor realized by printing techniques, Science, 265, 1684-1686 (1994).
52. H. Sirringhaus, T. Kawase, R. Friend, T. Shimoda, M. Inbasekaran, W. Wu and E. Woo, High-resolution inkjet printing of all-polymer transistor circuits, Science, 290, 2123-2126 (2000).
53. B. S. Ong, Y. Wu, P. Liu and S. Gardner, High-performance semiconducting polythiophenes for organic thin-film transistors, J. Am. Chem. Soc., 126, 3378-3379 (2004).
54. C. Waldauf, P. Schilinsky, M. Perisutti, J. Hauch and C. J. Brabec, Solution-processed organic n-type thin-film transistors, Adv. Mater., 15, 2084-2088 (2003).
55. T. M. Swager, The molecular wire approach to sensory signal amplification, Acc. Chem. Res., 31, 201-207 (1998).
56. H. Rockel, J. Huber, R. Gleiter and W. Schuhmann, Synthesis of functionalized poly(dithienylpyrrole) derivatives and their application in amperometric biosensors, Adv. Mater., 6, 568-571 (1994).
57. R. Pande, S. Kamtekar, M. S. Ayyagari, M. Kamath, K. A. Marx, J. Kumar, S. K. Tripathy and D. L. Kaplan, A biotinylated undecylthiophene copolymer bioconjugate for surface immobilization: creating an alkaline phos-phatase chemiluminescence-based biosensor, Bioconj. Chem., 7, 159-164 (1996).
58. A. Kumar, D. M. Welsh, M. C. Morvant, F. Piroux, K. A. Abboud and J. R. Reynolds, Conducting poly(3,4-alkylenedioxythiophene) derivatives as fast electrochromics with high-contrast ratio, Chem. Mater., 10, 896-902 (1998).
59. D. M. Welsh, A. Kumar, E. W. Meijer and J. R. Reynolds, Enhanced contrast ratio and rapid switching in electrochromics based on poly(3,4-propylenedioxythiophene) derivatives, Adv. Mater., 11, 1379-1382 (1999).
60. F. Garnier, Functionalized conducting polymers-towards intelligent materials, Adv. Mater., 1, 117-121 (1989).
61. K. Tamao, K. Sumitani, Y. Kiso, M. Zembayashi, A. Fujioka, S. Kodama, I. Nakajima, A. Minato and M. Kumada, Nickel-phosphine complex-catalyzed Grignard coupling. I. Cross-coupling of alkyl, aryl and alkenyl Grignard reagents with aryl and alkenyl halides: General scope and limitations, Bull. Chem. Soc. Jpn., 49, 1958-1969 (1976).
62. A. Suzuki, Synthetic studies via the cross-coupling reaction of organoboron derivatives with organic halides, PureAppl. Chem., 63, 419-422 (1991).
63. S. Kotha, K. Lahiri and D. Kashinath, Recent applications of the Suzuki-Miyaura cross-coupling reaction in organic synthesis, Tetrahedron, 58, 9633-9695 (2002).
64. K. Sonogashira, Y. Tohda and N. Hagihara, A convenient synthesis of acetylenes: catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes and bromopyridines, Tetrahedron Lett., 16, 4467-4470 (1975).
65. J. K. Stille, The palladium-catalyzed cross-coupling reactions of organotin reagents with organic electrophiles, Angew. Chem. Int. Ed. Engl., 25, 508-524 (1986).
66. M. Miyasaka and A. Rajca, Synthesis of functionalized carbon-sulfur [5]helicene: Pd-catalyzed Negishi cross-coupling between the β-positions of thiophenes, Synlett, 177-181 (2004).
67. R. Chinchilla, C. Najera and M. Yus, Metalated heterocycles and their applications in synthetic organic chemistry, Chem. Rev., 104, 2667-2722 (2004).
68. F. Jackel, M. D. Watson, K. Müllen and J. P. Rabe, Prototypical single-molecule chemical-field-effect transistor with nanometer-sized gates, Phys. Rev. Lett., 92, 188303 (2004).
69. 60 on a cyclothiophene monolayer template, Adv. Mater., 18, 447-451 (2006).
70. S. T. Purcell, N. Garcia, V. T. Binh, L. Jones II and J. M. Tour, Characterization of the conductivity of organic thiols by field emission microscopy and field emission spectroscopy, J. Am. Chem. Soc., 116, 11985-11989 (1994).
71. J. M. Tour, L. Jones, D. L. Pearson, J. J. S. Lamba, T. P. Burgin, G. M. Whitesides, D. L. Allara, A. N. Parikh and S. V. Atre, Self-assembled monolayers and multilayers of conjugated thiols, α,ω-dithiols and thioacetyl-containing adsorbates. Understanding attachments between potential molecular wires and gold surfaces, J. Am. Chem. Soc., 117, 9529-9534 (1995).
72. D. L. Pearson and J. M. Tour, Rapid syntheses of oligo(2,5-thiophene ethynylene)s with thioester termini: potential molecular scale wires with alligator clips, J. Org. Chem., 62, 1376-1387 (1997).
73. M. Tamura and H. Fujihara, Chiral bisphosphine BINAP-stabilized gold and palladium nanoparticles with small size and their palladium nanoparticle-catalyzed asymmetric reaction, J. Am. Chem. Soc., 125, 15742-15743 (2003).
74. B. C. Sih, A. Teichert and M. O. Wolf, Electrodeposition of oligothiophene-linked gold nanoparticle films, Chem. Mater., 16, 2712-2718 (2004).
75. C. Moorlag, B. C. Sih, T. L. Stott and M. O. Wolf, Metal-containing conjugated materials: oligomers, polymers and nanomaterials, J. Mater. Chem., 15, 2433-2436 (2005).
76. B. Liedberg, Z. Yang, I. Engquist, M. Wirde, U. Gelius, G. Götz, P. Bauerle, R. M. Rummel, C. Ziegler and W. Gopel, Self-assembly of α-functionalized terthiophenes on gold, J. Phys. Chem. B, 101, 5951-5962 (1997).
77. R. Michalitsch, A. El Kassmi, A. Yassar, P. Lang and F. Garnier, Increase of conjugation length within SAMs of terthiophene-derivatives, through electrochemical intermolecular coupling, J. Electroanal. Chem., 457, 129-139 (1998).
78. R. Michalitsch, A. El Kassmi, A. Yassar and F. Garnier, A practical synthesis of functionalized alkyl-oligothiophenes for molecular self-assembly, J. Heterocycl. Chem., 38, 649-653 (2001).
79. R. Michalitsch, C. Nogues, A. Najari, A. El Kassmi, A. Yassar, P. Lang and F. Garnier, β-Functionalized oligothiophenes for molecular self-assembly, Synth. Met., 101, 5-6 (1999).
80. L. Zhu, H. Tang, Y. Harima, K. Yamashita, D. Hirayama, Y. Aso and T. Otsubo, Electrochemical properties of self-assembled monolayers of tripod-shaped molecules and their applications to organic light-emitting diodes, Chem. Commun., 1830-1831 (2001).
81. L. Zhu, H. Tang, Y. Harima, K. Yamashita, Y. Aso and T. Otsubo, Enhanced hole injection in organic light-emitting diodes consisting of self-assembled monolayer of tripod-shaped π-conjugated thiols, J. Mater. Chem., 12, 2250-2254 (2002).
82. D. Hirayama, T. Yamashiro, K. Takimiya, Y. Aso, T. Otsubo, H. Norieda, H. Imahori and Y. Sakata, Preparation and photoelectrochemical properties of gold electrodes modified with [60]fullerene-linked oligothiophenes, Chem. Lett., 29, 570-571 (2000).
83. D. Hirayama, K. Takimiya, Y. Aso, T. Otsubo, T. Hasobe, H. Yamada, H. Imahori, S. Fukuzumi and Y. Sakata, Large photocurrent generation of gold electrodes modified with [60]fullerene-linked oligothiophenes bearing a tripodal rigid anchor, J. Am. Chem. Soc., 124, 532-533 (2002).
84. B. De Boer, H. Meng, D. F. Perepichka, J. Zhang, M. M. Frank, Y. J. Chabal and Z. Bao, Synthesis and characterization of conjugated mono-and dithiol oligomers and characterization of their self-assembled monolayers, Langmuir, 19, 4272-4284 (2003).
85. S. Taniguchi, M. Minamoto, M. M. Matsushita, T. Sugawara, Y. Kawada and D. Bethell, Electron transport in networks of gold nanoparticles connected by oligothiophene molecular wires, J. Mater. Chem., 16, 3459-3465 (2006).
86. W. Huang, G. Masuda, S. Maeda, H. Tanaka and T. Ogawa, Molecular junctions composed of oligothiophene dithiol-bridged gold nanoparticles exhibiting photoresponsive properties, Chem. Eur. J., 12, 607-619 (2006).
87. D. Bong, I. Tam and R. Breslow, Oligothiophene isocyanides for platinum-based molecular electronic applications, J. Am. Chem. Soc., 126, 11796-11797 (2004).
88. I. W. Tam, J. Yan and R. Breslow, An 11nm molecular wire that switches electrochemically between an insulating and a fully conjugated conducting state, Org. Lett., 8, 183-185 (2006).
89. X. Guo, J. P. Small, J. E. Klare, Y. Wang, M. S. Purewal, I. W. Tam, B. H. Hong, R. Caldwell, L. Huang, S. O'Brien, J. Yan, R. Breslow, S. J. Wind, J. Hone, P. Kim and C. Nuckolls, Covalently bridging gaps in single-walled carbon nanotubes with conducting molecules, Science, 311, 356-359 (2006).
90. J.-M. Lehn, Toward self-organization and complex matter, Science, 295, 2400-2403 (2002).
91. Y. Hong and L. L. Miller, An electrically conducting polyester that has isolated quaterthiophene units in the main chain, Chem. Mater., 7, 1999-2000 (1995).
92. Y. Kunugi, L. L. Miller, T. Maki and A. Canavesi, Photodiodes utilizing polyesters that contain different colored oligothiophenes in the main chain, Chem. Mater., 9, 1061-1062 (1997).
93. A. F. M. Kilbinger and W. J. Feast, Solution processable alternating oligothiophene-PEO-block-co-polymers: synthesis and evidence for solvent dependent aggregation, J. Mater. Chem., 10, 1777-1784 (2000).
94. O. Henze and W. J. Feast, The synthesis of amphiphilic sexithiophene-poly(ethylene oxide) segmented copoly-mers, J. Mater. Chem., 13, 1274-1278 (2003).
95. O. Henze, W. J. Feast, F. Gardebien, P. Jonkheijm, R. Lazzaroni, P. Leclere, E. W. Meijer and A. P. Schen-ning, Chiral amphiphilic self-assembled α,α'-linked quinque-, sexi-and septithiophenes: synthesis, stability and odd-even effects, J. Am. Chem. Soc., 128, 5923-5929 (2006).
96. P. Leclere, M. Surin, P. Viville, R. Lazzaroni, A. F. M. Kilbinger, O. Henze, W. J. Feast, M. Cavallini, F. Biscarini, A. P. H. J. Schenning and E. W. Meijer, About oligothiophene self-assembly: from aggregation in solution to solid-state nanostructures, Chem. Mater., 16, 4452-4466 (2004).
97. S. Westenhoff, A. Abrusci, W. J. Feast, O. Henze, A. F. M. Kilbinger, A. P. H. J. Schenning and C. Silva, Supramolecular electronic coupling in chiral oligothiophene nanostructures, Adv. Mater., 18, 1281-1285 (2006).
98. W. Li, T. Maddux and L. Yu, Synthesis and characterization of diblock copolymers containing oligothiophenes with defined regiospecificity and molecular weights, Macromolecules, 29, 7329-7334 (1996).
99. M. A. Hempenius, B. M. W. Langeveld-Voss, J. A. E. H. v. Haare, R. A. J. Janssen, S. S. Sheiko, J. P. Spatz, M. Moller and E. W. Meijer, A polystyrene-oligothiophene-polystyrene triblock copolymer, J. Am. Chem. Soc., 120, 2798-2804 (1998).
100. T. Hayakawa and H. Yokoyama, Fabrication of self-organized chemically and topologically heterogeneous patterns on the surface of polystyrene-β-oligothiophene block copolymer films, Langmuir, 21, 10288-10291 (2005).
101. S.-i. Kawano, N. Fujita and S. Shinkai, Quater-, quinque-and sexithiophene organogelators: unique ther-mochromism and heating-free sol-gel phase transition, Chem. Eur. J., 11, 4735-4742 (2005).
102. M. Melucci, G. Barbarella, M. Gazzano, M. Cavallini, F. Biscarini, A. Bongini, F. Piccinelli, M. Monari, M. Bandini, A. Umani-Ronchi and P. Biscarini, Synthesis, multiphase characterization and helicity control in chiral DACH-linked oligothiophenes, Chem. Eur. J., 12, 7304-7312 (2006).
103. K. Nawa, I. Imae, N. Noma and Y. Shirota, Synthesis of a novel type of electrochemically doped vinyl polymer containing pendant terthiophene and its electrical and electrochromic properties, Macromolecules, 28, 723-729 (1995).
104. I. Imae, K. Nawa, Y. Ohsedo, N. Noma and Y. Shirota, Synthesis of a novel family of electrochemically-doped vinyl polymers containing pendant oligothiophenes and their electrical and electrochromic properties, Macro-molecules, 30, 380-386 (1997).
105. Y. Ohsedo, I. Imae and Y. Shirota, Synthesis and electrochromic properties of a new family of methacrylate polymers containing pendant oligothiophenes, J. Polym. Sci. B: Polym. Phys., 41, 2471-2484 (2003).
106. M. Melucci, G. Barbarella, M. Zambianchi, M. Benzi, F. Biscarini, M. Cavallini, A. Bongini, S. Fabbroni, M. Mazzeo, M. Anni and G. Gigli, Poly(a-vinyl-a>-alkyloligothiophene) side-chain polymers. Synthesis, fluorescence and morphology, Macromolecules, 37, 5692-5702 (2004).
107. T. Hayakawa and S. Horiuchi, From angstroms to micrometers: Self-organized hierarchical structure within a polymer film, Angew. Chem. Int. ed., 42, 2285-2289 (2003).
108. M. Melucci, C. Dionigi, G. Lanzani, I. Viola, G. Gigli and G. Barbarella, Shaping thiophene oligomers into fluorescent nanobeads forming two-dimensionally patterned assemblies by the capillary effect, Macromolecules, 38, 10050-10054 (2005).
109. C. Zhao, Y. Zhang, C. Wang, L. Rothberg and M. K. Ng, Synthesis of homopolymer containing diphenyl end-capped oligothiophene co-oligomer unit in the side-chain, Org. Lett., 8, 1585-1588 (2006).
110. D. Byron, A. Matharu, R. Wilson and G. Wright, The synthesis and liquid crystal properties of certain 5,5'-disubstituted 2,2':5',2'-terthiophenes, Mol. Cryst. Liq. Cryst, 265, 61-76 (1995).
111. R. Azumi, G. Gotz and P. Bauerle, Thermal behaviour of α-alkylated oligothiophenes, Synth. Met., 101, 544-545 (1999).
112. S. Ponomarenko and S. Kirchmeyer, Synthesis and thermal behaviour of α,α'-didecyloligothiophenes, J. Mater. Chem., 13, 197-202 (2003).
113. J. Leroy, J. Levin, S. Sergeyev and Y. Geerts, Practical one-step synthesis of symmetrical liquid crystalline dialkyloligothiophenes for molecular electronic applications, Chem. Lett., 35, 166-167 (2006).
114. M. Funahashi and J.-I. Hanna, High ambipolar carrier mobility in self-organizing terthiophene derivative, Appl. Phys. Lett., 76, 2574-2576 (2000).
115. T. Yamada, R. Azumi, H. Tachibana, H. Sakai, M. Abe, P. Bauerle and M. Matsumoto, Liquid crystalline behavior of α-substituted oligothiophenes, Chem. Lett., 30, 1022-1023 (2001).
116. H. Zhang, S. Shiino, A. Shishido, A. Kanazawa, O. Tsutsumi, T. Shiono and T. Ikeda, A thiophene liquid crystal as a novel π-conjugated dye for photo-manipulation of molecular alignment, Adv. Mater., 12, 1336-1339 (2000).
117. M. Yaegashi, A. Shishido, T. Shiono and T. Ikeda, Effect of ester moieties in dye structures on photoinduced reorientation of dye-doped liquid crystals, Chem. Mater., 17, 4304-4309 (2005).
118. A. J. J. M. Van Breemen, P. T. Herwig, C. H. T. Chlon, J. Sweelssen, H. F. M. Schoo, S. Setayesh, W. M. Hardeman, C. A. Martin, D. M. de Leeuw, J. J. P. Valeton, C. W. M. Bastiaansen, D. J. Broer, A. R. Popa-Merticaru and S. C. J. Meskers, Large area liquid crystal monodomain field-effect transistors, J. Am. Chem. Soc., 128, 2336-2345 (2006).
119. B.-H. Huisman, J. J. P. Valeton, W. Nijssen, J. Lub and W. ten Hoeve, Oligothiophene-based networks applied for field-effect transistor, Adv. Mater., 15, 2002-2005 (2003).
120. I. McCulloch, W. Zhang, M. Heeney, C. Bailey, M. Giles, D. Graham, M. Shkunov, D. Sparrowe and S. Tierney, Polymerisable liquid crystalline organic semiconductors and their fabrication in organic field effect transistors, J. Mater. Chem., 13, 2436-2444 (2003).
121. -1 at ambient temperatures in thiophene-based smectic liquid crystals, Adv. Mater., 17, 594-598 (2005).
122. M. Funahashi and N. Tamaoki, Electronic conduction in the chiral nematic phase of an oligothiophene derivative, ChemPhysChem, 7, 1193-1197 (2006).
123. S. Lightowler and M. Hird, Monodisperse aromatic oligomers of defined structure and large size through selective and sequential Suzuki palladium-catalyzed cross-coupling reactions, Chem. Mater., 17, 5538-5549 (2005).
124. P. Liu, Y. Zhang, G. Feng, J. Hu, X. Zhou, Q. Zhao, Y. Xu, Z. Tong and W. Deng, Synthesis and liquid crystal properties of a novel family of oligothiophene derivatives, Tetrahedron, 60, 5259-5264 (2004).
125. P. Liu, M. Liu and W. Deng, Synthesis and mesogenic properties of novel terthiophene derivatives., Synth. Commun., 36, 685-692 (2006).
126. T. Yasuda, K. Kishimoto and T. Kato, Columnar liquid crystalline π-conjugated oligothiophenes, Chem. Com-mun., 3399-3401 (2006).
127. M. Kimura, T. Yasuda, K. Kishimoto, G. Gotz, P. Bauerle and T. Kato, Oligothiophene-based liquid crystals exhibiting smectic A phases in wider temperature ranges, Chem. Lett., 35, 1150-1151 (2006).
128. A. P. H. J. Schenning, A. F. M. Kilbinger, F. Biscarini, M. Cavallini, H. J. Cooper, P. J. Derrick, W. J. Feast, R. Lazzaroni, P. Leclere, L. A. McDonell, E. W. Meijer and S. C. J. Meskers, Supramolecular organization of α,α'-disubstituted sexithiophenes, J. Am. Chem. Soc., 124, 1269-1275 (2002).
129. D. Didier, S. Sergeyev and Y. H. Geerts, Non-symmetrical oligothiophenes with 'incompatible' substituents, Tetrahedron, 63, 941-946 (2007).
130. P. Bauerle, U. Segelbacher, A. Maier and M. Mehring, Electronic structure of mono-and dimeric cation radicals in end-capped oligothiophenes, J. Am. Chem. Soc., 115, 10217-10223 (1993).
131. P. Bauerle, U. Segelbacher, K. U. Gaudl, D. Huttenlocher and M. Mehring, Didodecylsexithiophene-a model compound for the formation and characterization of charge carriers in conjugated chains, Angew. Chem. Int. Ed. Engl., 32, 76-78 (1993).
132. L. L. Miller and K. R. Mann, π-Dimers and π-stacks in solution and in conducting polymers, Acc. Chem. Res., 29, 417-423 (1996).
133. D. D. Graf, R. G. Duan, J. P. Campbell, L. L. Miller and K. R. Mann, From monomers to π-stacks. A comprehensive study of the structure and properties of monomeric, π-dimerized and π-stacked forms of the cation radical of 3',4'-dibutyl-2,5''-diphenyl-2,2':5',2''-terthiophene, J. Am. Chem. Soc., 119, 5888-5899 (1997).
134. T. Kaikawa, K. Takimiya, Y. Aso and T. Otsubo, Synthesis and spectroscopic properties of [2.2] quinquethio-phenophane as an ideal π-dimer model, Org. Lett., 2, 4197-4199 (2000).
135. T. Satou, T. Sakai, T. Kaikawa, K. Takimiya, T. Otsubo and Y. Aso, α, ω-Bis(qmnquethienyl)aUkanes as a π-dimer model of polythiophene, Org. Lett., 6, 997-1000 (2004).
136. T. Sakai, T. Satou, T. Kaikawa, K. Takimiya, T. Otsubo and Y. Aso, Syntheses, structures, spectroscopic properties and π-dimeric interactions of [n.n]quinquethiophenophanes, J. Am. Chem. Soc., 127, 8082-8089 (2005).
137. C. Edder and J. M. J. Fréchet, Synthesis of bridged oligothiophenes: toward a new class of thiophene-based electroactive surfactants, Org. Lett., 5, 1879-1882 (2003).
138. K. M. Knoblock, C. J. Silvestri and D. M. Collard, Stacked conjugated oligomers as molecular models to examine interchain interactions in conjugated materials, J. Am. Chem. Soc., 128, 13680-13681 (2006).
139. F. Steybe, F. Effenberger, S. Beckmann, P. Kramer, C. Glania and R. Wortmann, Enhanced nonlinear optical properties and thermal stability of donor-acceptor substituted oligothiophenes, Chem. Phys., 219, 317-331 (1997).
140. F. Steybe, F. Effenberger, U. Gubler, C. Bosshard and P. Gunter, Highly polarizable chromophores for nonlinear optics: syntheses, structures and properties of donor-acceptor substituted thiophenes and oligothiophenes, Tetrahedron, 54, 8469-8480 (1998).
141. M. M. M. Raposo, A. M. C. Fonseca and G. Kirsch, Synthesis of donor-acceptor substituted oligothiophenes by Stille coupling, Tetrahedron, 60, 4071-4078 (2004).
142. V. P. Rao, A. K.-Y. Jen, K. Y. Wong and K. J. Drost, Novel push-pull thiophenes for second order nonlinear optical applications, Tetrahedron Lett., 34, 1747-1750 (1993).
143. A. K.-Y. Jen, V. P. Rao, K. Y. Wong and K. J. Drost, Functionalized thiophenes: second-order nonlinear optical materials, J. Chem. Soc., Chem. Commun., 90-93 (1993).
144. V. P. Rao, A. K.-Y. Jen, K. Y. Wong and K. J. Drost, Dramatically enhanced second-order nonlinear optical susceptibilities in tricyanovinylthiophene derivatives, J. Chem. Soc., Chem. Commun., 1118-1120 (1993).
145. F. Effenberger, F. Wurthner and F. Steybe, Synthesis and solvatochromic properties of donor-acceptor-substituted oligothiophenes, J. Org. Chem., 60, 2082-2091 (1995).
146. T. Noda and Y. Shirota, 5,5'-Bis(dimesitylboryl)-2,2'-bithiophene and 5,5"-bis(dimesitylboryl)-2,2':5',2"-terthiophene as a novel family of electron-transporting amorphous molecular materials, J. Am. Chem. Soc., 120, 9714-9715 (1998).
147. Y. Shirota, T. Noda and H. Ogawa, Organic light-emitting diodes using novel emitting amorphous molecular materials, Proc. SPIE, 3797, 158-169 (1999).
148. H. Doi, M. Kinoshita, K. Okumoto and Y. Shirota, A novel class of emitting amorphous molecular materials with bipolar character for electroluminescence, Chem. Mater., 15, 1080-1089 (2003).
149. T. Noda, I. Imae, N. Noma and Y. Shirota, 5,5"-Bis{4-[bis(4-methylphenyl)amino]phenyl}-2,2':5',2"-terthiophene and 5,5'"-bis{4-[bis(4-methylphenyl)amino]phenyl}-2,2':5',2":5",2"'-quaterthiophene as a novel family of amorphous molecular materials, Adv. Mater., 9, 239-241 (1997).
150. T. Noda, H. Ogawa, N. Noma and Y. Shirota, Organic light-emitting diodes using a novel family of amorphous molecular materials containing an oligothiophene moiety as color-tunable emitting materials, J. Mater. Chem., 9, 2177-2181 (1999).
151. C. M. Castro, M. C. Ruiz Delgado, V. Hernandez, Y. Shirota, J. Casado and J. T. Lopez Navarrete, Vibrational spectroscopic features of a novel family of amorphous molecular materials containing an oligothiophene moiety as color-tunable emitting materials, J. Phys. Chem. B, 106, 7163-7170 (2002).
152. O. Clot, D. Selmarten and M. J. McNevin, Synthesis and characterization of amino-capped oligothiophene-based hole-transport materials, J. Mater. Chem., 15, 4934-4942 (2005).
153. J.-M. Raimundo, P. Blanchard, I. Ledoux-Rak, R. Hierle, L. Michaux and J. Roncali, Huge enhancement of the quadratic nonlinear optical susceptibility in push-pull chromophores based on bridged dithienylethylene spacers, Chem. Commun., 1597-1598 (2000).
154. J. M. Raimundo, P. Blanchard, P. Fröre, N. Mercier, I. Ledoux Rak, R. Hierle and J. Roncali, Push-pull chromophores based on 2,2'-bi(3,4-ethylenedioxythiophene) (BEDOT) π-conjugating spacer, Tetrahedron Lett., 42, 1507-1510 (2001).
155. J. M. Raimundo, P. Blanchard, N. Gallego-Planas, N. Mercier, I. Ledoux-Rak, R. Hierle and J. Roncali, Design and synthesis of push-pull chromophores for second-order nonlinear optics derived from rigidified thiophene-based π-conjugating spacers, J. Org. Chem., 67, 205-218 (2002).
156. M. C. Ruiz Delgado, V. Hernandez, J. Casado, J. T. Lopez Navarrete, J.-M. Raimundo, P. Blanchard and J. Roncali, Vibrational and quantum-chemical study of push-pull chromophores for second-order nonlinear optics from rigidified thiophene-based π-conjugating spacers, Chem. Eur. J., 9, 3670-3682 (2003).
157. G. Gotz, S. Scheib, R. Klose, J. Heinze and P. Bauerle, Synthesis and properties of a series of regioregularly amino-substituted oligo-and polythiophenes, Adv. Funct. Mater., 12, 723-728 (2002).
158. K.-T. Wong, T. H. Hung, C. H. Chou, Y. O. Su and S. C. Kao, Synthesis and properties of novel bis(triarylamines) based on a 3,3'-diphenyl-2,2'-bithiophene core, Chem. Commun., 1628-1629 (2001).
159. P. Gerstner, D. Rohde and H. Hartmann, A versatile route to N,N'-(peraryl)substituted 5,5'-diamino-2,2'-bithiophenes, Synthesis, 2487-2489 (2002).
160. A. Tabet, A. Schroder, H. Hartmann, D. Rohde and L. Dunsch, Preparation and characterization of α,α'-bisdiarylamino-capped oligothiophenes, Org. Lett., 5, 1817-1820 (2003).
161. A. Tabet and H. Hartmann, Stille coupling of 2-diarylaminothiophenes with mono-and dibromo(het)arylenes, Synthesis, 610-616 (2005).
162. D. Rohde, L. Dunsch, A. Tabet, H. Hartmann and J. Fabian, Radical ions of α, a'-bis(diphenylamino)-capped oligothiophenes: a combined spectroelectrochemical and theoretical study, J. Phys. Chem. B, 110, 8223-8231 (2006).
163. N. Koumura, Z. S. Wang, S. Mori, M. Miyashita, E. Suzuki and K. Hara, Alkyl-functionalized organic dyes for efficient molecular photovoltaics, J. Am. Chem. Soc., 128, 14256-14257 (2006).
164. nCN (n = 3-6), Chem. Mater., 9, 981-990 (1997).
165. M. Melucci, G. Barbarella, M. Zambianchi, P. Di Pietro and A. Bongini, Solution-phase microwave-assisted synthesis of unsubstituted and modified α-quinque-and sexithiophenes, J. Org. Chem., 69, 4821-4828 (2004).
166. G. Zotti, S. Zecchin, B. Vercelli, A. Berlin, J. Casado, V. Hernandez, R. P. Ortiz, J. T. Lopez Navarrete, E. Orti, P. M. Viruela and B. Milian, Magnetic and conductive properties of quinoidal oligothiophenes, Chem. Mater., 18, 1539-1545 (2006).
167. M. V. Joshi, M. P. Cava, M. V. Lakshmikantham, R. M. Metzger, H. Abdeldayem, M. Henry and P. Venkateswarlu, Third-order non-linear optical suceptibilities by laser self-trapping and degenerate four-wave mixing in oligothienyldicyanovinylene solutions, Synth. Met., 57, 3974-3979 (1993).
168. T. M. Pappenfus, M. W. Burand, D. E. Janzen and K. R. Mann, Synthesis and characterization of tricyanovinyl-capped oligothiophenes as low-bandgap organic materials, Org. Lett., 5, 1535-1538 (2003).
169. M. M. Bader, R. Custelcean and M. D. Ward, Tricyanovinyl-substituted oligothiophenes, Chem. Mater., 15, 616-618 (2003).
170. H. Higuchi, T. Nakayama, H. Koyama, J. Ojima, T. Wada and H. Sasabe, Synthesis and properties of α,ω-disubstituted oligo(3-hexylthiophene)s and oligothienoquinonoids in head-to-head orientation, Bull. Chem. Soc. Jpn., 68, 2363-2377 (1995).
171. T. M. Pappenfus, R. J. Chesterfield, C. D. Frisbie, K. R. Mann, J. Casado, J. D. Raff and L. L. Miller, A π-stacking terthiophene-based quinodimethane is an n-channel conductor in a thin film transistor, J. Am. Chem. Soc., 124, 4184-4185 (2002).
172. D. E. Janzen, M. W. Burand, P. C. Ewbank, T. M. Pappenfus, H. Higuchi, D. A. da Silva Filho, V. G. Young, J.-L. Bredas and K. R. Mann, Preparation and characterization of π-stacking quinodimethane oligothiophenes. Predicting semiconductor behavior and bandwidths from crystal structures and molecular orbital calculations, J. Am. Chem. Soc., 126, 15295-15308 (2004).
173. T. Takahashi, K. Matsuoka, K. Takimiya, T. Otsubo and Y. Aso, Extensive quinoidal oligothiophenes with dicyanomethylene groups at terminal positions as highly amphoteric redox molecules, J. Am. Chem. Soc., 127, 8928-8929 (2005).
174. R. P. Ortiz, J. Casado, V. Hernandez, J. T. Lopez Navarrete, E. Orti, P. M. Viruela, B. Milian, S. Hotta, G. Zotti, S. Zecchin and B. Vercelli, Magnetic properties of quinoidal oligothiophenes: more than good candidates for ambipolar organic semiconductors?, Adv. Funct. Mater., 16, 531-536 (2006).
175. R. J. Chesterfield, C. R. Newman, T. M. Pappenfus, P. C. Ewbank, M. H. Haukaas, K. R. Mann, L. L. Miller and C. D. Frisbie, High electron mobility and ambipolar transport in organic thin-film transistors based on a π-stacking quinoidal terthiophene, Adv. Mater., 15, 1278-1282 (2003).
176. J. Casado, R. P. Ortiz, M. C. Ruiz Delgado, R. Azumi, R. T. Oakley, V. Hernaindez and J. T. Loipez Navar-rete, Multidisciplinary physicochemical analysis of oligothiophenes end-capped by nitriles: electrochemistry, UV-Vis-near-IR, IR and Raman spectroscopies and quantum chemistry, J. Phys. Chem. B, 109, 10115-10125 (2005).
177. C. R. Newman, C. D. Frisbie, D. A. da Silva Filho, J. L. Bredas, P. C. Ewbank and K. R. Mann, Introduction to organic thin film transistors and design of n-channel organic semiconductors, Chem. Mater., 16, 4436-4451 (2004).
178. 60, Adv. Mater., 18, 2872-2875 (2006).
179. K. Schulze, C. Uhrich, R. Schüppel, K. Leo, M. Pfeiffer, E. Brier, E. Reinold and P. Bauerle, Efficient hetero-junction organic solar cells with high photovoltage containing a low gap oligothiophene derivative, Proc. SPIE, 6192, 61920C (2006).
180. T. Takahashi, K. Takimiya, T. Otsubo and Y. Aso, Synthesis and spectral properties of a highly soluble push-pull type of quinoidal thiophenes, Org. Lett., 7, 4313-4316 (2005).
181. M. Uno, K. Seto, M. Masuda, W. Ueda and S. Takahashi, A new route to phenylenedimalononitrile and the analogues using palladium-catalyzed carbon-carbon bond formation, Tetrahedron Lett., 26, 1553-1556 (1985).
182. M. Uno, K. Seto and S. Takahashi, A new method of synthesis of arylmalononitriles catalysed by a palladium complex, J. Chem. Soc., Chem. Commun., 932-933 (1984).
183. G. Barbarella, L. Favaretto, G. Sotgiu, M. Zambianchi, A. Bongini, C. Arbizzani, M. Mastragostino, M. Anni, G. Gigli and R. Cingolani, Tuning solid-state photoluminescence frequencies and efficiencies of oligomers containing one central thiophene-S, S-dioxide unit, J. Am. Chem. Soc., 122, 11971-11978 (2000).
184. A. Bongini, G. Barbarella, L. Favaretto, G. Sotgiu, M. Zambianchi and D. Casarini, Conformational profile, energy barriers and optical properties of quinquethiophene-5,5-dioxides, Tetrahedron, 58, 10151-10158 (2002).
185. B. Jousselme, P. Blanchard, M. Allain, E. Levillain, M. Dias and J. Roncali, Structural control of the electronic properties of photodynamic azobenzene-derivatized π-conjugated oligothiophenes, J. Phys. Chem. A, 110, 3488-3494 (2006).
186. K. Hara, M. Kurashige, Y. Dan-oh, C. Kasada, A. Shinpo, S. Suga, K. Sayama and H. Arakawa, Design of new coumarin dyes having thiophene moieties for highly efficient organic-dye-sensitized solar cells, New J. Chem., 27, 783-785 (2003).
187. K. Hara, Z. S. Wang, T. Sato, A. Furube, R. Katoh, H. Sugihara, Y. Dan-oh, C. Kasada, A. Shinpo and S. Suga, Oligothiophene-containing coumarin dyes for efficient dye-sensitized solar cells, J. Phys. Chem. B, 109, 15476-15482 (2005).
188. K. Hara, K. Miyamoto, Y. Abe and M. Yanagida, Electron transport in coumarin-dye-sensitized nanocrystalline TiO2 electrodes, J. Phys. Chem. B, 109, 23776-23778 (2005).
189. J. Cremer, E. Mena-Osteritz, N. G. Pschierer, K. Müllen and P. Bauerle, Dye-functionalized head-to-tail coupled oligo(3-hexylthiophenes)-perylene-oligothiophene dyads for photovoltaic applications, Org. Biomol. Chem., 3, 985-995 (2005).
190. J. Cremer and P. Bauerle, Perylene-oligothiophene-perylene triads for photovoltaic applications, Eur. J. Org. Chem., 3715-3723 (2005).
191. E. Fron, M. Lor, R. Pilot, G. Schweitzer, H. Dincalp, S. De Feyter, J. Cremer, P. Bauerle, K. Mullen, M. Van der Auweraer and F. C. De Schryver, Photophysical study of photoinduced electron transfer in a bis-thiophene substituted peryleneimide, Photochem. Photobiol. Sci., 4, 61-68 (2005).
192. S. Chen, Y. Liu, W. Qiu, X. Sun, Y. Ma and D. Zhu, Oligothiophene-functionalized perylene bisimide system: synthesis, characterization and electrochemical polymerization properties, Chem. Mater., 17, 2208-2215 (2005).
193. N. S. Sariciftci, L. Smilowitz, A. J. Heeger and F. Wudl, Photoinduced electron transfer from a conducting polymer to buckminsterfullerene, Science, 258, 1474-1476 (1992).
194. F. Padinger, R. S. Rittberger and N. S. Sarififtci, Effects of postproduction treatment on plastic solar cells, Adv. Funct. Mater., 13, 85-88 (2003).
195. G. Li, V. Shrotriya, J. Huang, Y. Yao, T. Moriarty, K. Emery and Y. Yang, High-efficiency solution processable polymer photovoltaic cells by self-organization of polymer blends, Nat. Mater., 4, 864-868 (2005).
196. W. Ma, C. Yang, X. Gong, K. Lee and A. J. Heeger, Thermally stable, efficient polymer solar cells with nanoscale control of the interpenetrating network morphology, Adv. Funct. Mater., 15, 1617-1622 (2005).
197. M. Granstrom, K. Petritsch, A. C. Arias, A. Lux, M. R. Andersson and R. H. Friend, Laminated fabrication of polymeric photovoltaic diodes, Nature, 395, 257-260 (1998).
198. L. A. A. Pettersson, S. R. Lucimara and O. Inganas, Modeling photocurrent action spectra of photovoltaic devices based on organic thin films, J. Appl. Phys., 86, 487-496 (1999).
199. A. Gadisa, M. Svensson, M. R. Andersson and O. Inganas, Correlation between oxidation potential and open-circuit voltage of composite solar cells based on blends of polythiophenes/fullerene derivative, Appl. Phys. Lett., 84, 1609-1611 (2004).
200. A. Cravino and N. S. Sariciftci, Double-cable polymers for fullerene based organic optoelectronic applications, J. Mater. Chem., 12, 1931-1943 (2002).
201. T. Otsubo, Y. Aso and K. Takimiya, Fullerene-tethered oligothiophenes as advanced molecular electronic materials, PureAppl. Chem., 77, 2003-2010 (2005).
202. T. Benincori, E. Brenna, F. Sannicolo, L. Trimarco, G. Zotti and P. Sozzani, The first 'charm bracelet' conjugated polymer: an electroconducting polythiophene with covalently bound fullerene moieties, Angew. Chem. Int. Ed. Engl., 35, 648-651 (1996).
203. A. Yassar, M. Hmyene, D. C. Loveday and J. P. Ferraris, Synthesis and characterization of polythiophenes functionalized by buckminsterfullerene, Synth. Met., 84, 231-232 (1997).
204. A. Cravino, G. Zerza, M. Maggini, S. Bucella, M. Svensson, M. R. Andersson, H. Neugebauer and N. S. Sariciftci, A novel polythiophene with pendant fullerenes: toward donor/acceptor double-cable polymers, Chem. Commun., 2487-2488 (2000).
205. A. Cravino, G. Zerza, H. Neugebauer, M. Maggini, S. Bucella, E. Menna, M. Svensson, M. R. Andersson, C. J. Brabec and N. S. Sariciftci, Electrochemical and photophysical properties of a novel polythiophene with pendant fulleropyrrolidine moieties: toward 'double cable' polymers for optoelectronic devices, J. Phys. Chem. B, 106, 70-76 (2002).
206. K. Sivula, Z. T. Ball, N. Watanabe and J. M. J. Frechet, Amphiphilic diblock copolymer compatibilizers and their effect on the morphology and performance of polythiophene:fullerene solar cells, Adv. Mater., 18, 206-210 (2006).
207. Y. Murata, M. Suzuki and K. Komatsu, Synthesis and electropolymerization of fullerene-terthiophene dyads, Org. Biomol. Chem., 1, 2624-2625 (2003).
208. 2-C(R)≡C [C4HS(C4HbS-2)2-2,5]}], J. Chem. Soc., Dalton Trans., 1893-1898 (1998).
209. T. Yamazaki, Y. Murata, K. Komatsu, K. Furukawa, M. Morita, N. Maruyama, T. Yamao and S. Fujita, Synthesis and electrolytic polymerization of the ethylenedioxy-substituted terthiophene-fullerene dyad, Org. Lett., 6, 4865-4868 (2004).
210. F. Wang, M. S. Wilson, R. D. Rauh, P. Schottland, B. C. Thompson and J. R. Reynolds, Electrochromic linear and star branched poly(3,4-ethylenedioxythiophene-didodecyloxybenzene) polymers, Macromolecules, 33, 2083-2091 (2000).
211. 60 on a conjugated polymer, Adv. Mater., 17, 897-900 (2005).
212. F. Effenberger and G. Grube, Synthesis of oligothienylfullerenes, Synthesis, 1372-1379 (1998).
213. S. Knorr, A. Grupp, M. Mehring, G. Grube and F. Effenberger, Photo-induced electron-transfer processes in (anthracene-) quinquethiophene-fullerene diads and triads, J. Chem. Phys., 110, 3502-3508 (1999).
214. 60 and a conjugated dimethylaniline-substituted dithienylethylene donor, J. Org. Chem., 64, 4884-4886 (1999).
215. T. Yamashiro, Y. Aso, T. Otsubo, H. Tang, Y. Harima and K. Yamashita, Intramolecular energy transfer of [60]fullerene-linked oligothiophenes, Chem. Lett., 28, 443-444 (1999).
216. 60: synthesis, characterization and functionalization of fullerene pyrrolidines, J. Am. Chem. Soc., 115, 9798-9799 (1993).
217. 60 dyad studied by pico-and nanosecond laser flash photolysis in the near-IR region, J. Phys. Chem. A, 104, 4876-4881 (2000).
218. 60 dyad molecules, J. Phys. Chem. B, 105, 9930-9934 (2001).
219. N. Negishi, K. Yamada, K. Takimiya, Y. Aso, T. Otsubo and Y. Harima, Oligothiophene/fullerene dyads as active photovoltaic materials, Chem. Lett., 32, 404-405 (2003).
220. P. A. van Hal, J. Knol, B. M. W. Langeveld-Voss, S. C. J. Meskers, J. C. Hummelen and R. A. J. Janssen, Photoinduced energy and electon transfer in fullerene-oligothiophene-fullerene triads, J. Phys. Chem. A, 104, 5974-5988 (2000).
221. N. Negishi, K. Takimiya, T. Otsubo, Y. Harima and Y. Aso, Synthesis and photovoltaic effects of oligothiophenes incorporated with two [60]fullerenes, Chem. Lett., 33, 654-655 (2004).
222. Y. Kunugi, K. Takimiya, N. Negishi, T. Otsubo and Y. Aso, An ambipolar organic field-effect transistor using oligothiophene incorporated with two [60]fullerenes, J. Mater. Chem., 14, 2840-2841 (2004).
223. N. Negishi, K. Takimiya, T. Otsubo, Y. Harima and Y. Aso, Oligothiophene-multifullerene linkage molecules as high performance photovoltaic materials, Synth. Met., 152, 125-128 (2005).
224. H. Kanato, K. Takimiya, T. Otsubo, Y. Aso, T. Nakamura, Y. Araki and O. Ito, Synthesis and photophysical properties of ferrocene-oligothiophene-fullerene triads, J. Org. Chem., 69, 7183-7189 (2004).
225. T. Nakamura, H. Kanato, Y. Araki, O. Ito, K. Takimiya, T. Otsubo and Y. Aso, Effects of extension or prevention of π-conjugation on photoinduced electron transfer processes of ferrocene-oligothiophene-fullerene triads, J. Phys. Chem. A, 110, 3471-3479 (2006).
226. E. Elandaloussi, P. Fröre and J. Roncali, Extensively π-conjugated soluble oligothienylenevinylenes, Chem. Commun., 301-302 (1997).
227. 60, Adv. Mater., 14, 283-287 (2002).
228. J.J. Apperloo, C. Martineau, P. A. van Hal, J. Roncali and R. A. J. Janssen, Intra-and intermolecular photoinduced energy and electron transfer between oligothienylenevinylenes and N-methylfulleropyrrolidine, J. Phys. Chem. A, 106, 21-31 (2002).
229. Y. Obara, K. Takimiya, Y. Aso and T. Otsubo, Synthesis and photophysical properties of [60]fullerene-oligo(thienylene-ethynylene) dyads, Tetrahedron Lett., 42, 6877-6881 (2001).
230. Y. Aso, Y. Obara, T. Okai, S. Nishiguchi and T. Otsubo, Synthesis and properties of coil-shaped 2,3-thienylene-ethynylene oligomers, Mol. Cryst. Liq. Cryst., 376, 153-158 (2002).
231. 60 dyads, Chem. Eur. J., 8, 5415-5429 (2002).
232. 60-derivatized poly(thiophene)s from tailored precursors, Macromolecules, 36, 3020-3025 (2003).
233. M. Narutaki, K. Takimiya, T. Otsubo, Y. Harima, H. Zhang, Y. Araki and O. Ito, Synthesis and photophysical properties of two dual oligothiophene-fullerene linkage molecules as photoinduced long-distance charge separation systems, J. Org. Chem., 71, 1761-1768 (2006).
234. H. Kanato, M. Narutaki, K. Takimiya, T. Otsubo and Y. Harima, Synthesis and photovoltaic properties of tetrathiafulvalene-oligothiophene-fullerene triads, Chem. Lett., 35, 668-669 (2006).
235. C. H. Huang, N. D. McClenaghan, A. Kuhn, J. W. Hofstraat and D. M. Bassani, Enhanced photovoltaic response in hydrogen-bonded all-organic devices, Org. Lett., 7, 3409-3412 (2005).
236. C.-H. Huang, N. D. McClenaghan, A. Kuhn, G. Bravic and D. M. Bassani, Hierarchical self-assembly of all-organic photovoltaic devices, Tetrahedron, 62, 2050-2059 (2006).
237. F. Wurthner, M. S. Vollmer, F. Effenberger, P. Emele, D. U. Meyer, H. Port and H. C. Wolf, Synthesis and energy transfer properties of terminally substituted oligothiophenes, J. Am. Chem. Soc., 117, 8090-8099 (1995).
238. M. S. Vollmer, F. Wurthner, F. Effenberger, P. Emele, D. U. Meyer, T. Stumpfig, H. Port and H. C. Wolf, Anthryloligothienylporphyrins: energy transfer and light-harvesting systems, Chem. Eur. J., 4, 260-269 (1998).
239. J. S. Lindsey, I. C. Schreiman, H. C. Hsu, P. C. Kearney and A. M. Marguerettaz, Rothemund and Adler-Longo reactions revisited: synthesis of tetraphenylporphyrins under equilibrium conditions, J. Org. Chem., 52, 827-836 (1987).
240. F. C. Krebs and H. Spanggaard, Antibatic photovoltaic response in zinc-porphyrin-linked oligothiophenes, Sol. Energy Mater. Sol. Cells, 88, 363-375 (2005).
241. F. Odobel, S. Suresh, E. Blart, Y. Nicolas, J. P. Quintard, P. Janvier, J. Y. Le Questel, B. Illien, D. Rondeau, P. Richomme, T. Haupl, S. Wallin and L. Hammarstrom, Synthesis of oligothiophene-bridged bisporphyrins and study of the linkage dependence of the electronic coupling, Chem. Eur. J., 8, 3027-3046 (2002).
242. T. G. Zhang, Y. Zhao, I. Asselberghs, A. Persoons, K. Clays and M. J. Therien, Design, synthesis, linear and nonlinear optical properties of conjugated (porphinato)zinc(II)-based donor-acceptor chromophores featuring nitrothiophenyl and nitrooligothiophenyl electron-accepting moieties, J. Am. Chem. Soc., 127, 9710-9720 (2005).
243. M. Schaferling and P. Bauerle, Synthesis and properties of porphyrin-functionalized poly(bithiophenes), Synth. Met., 101, 38-39 (1999).
244. M. Schaferling and P. Bauerle, Porphyrin-functionalized oligo-and polythiophenes, J. Mater. Chem., 14, 1132-1141 (2004).
245. M. Takeuchi, T. Shioya and T. M. Swager, Allosteric fluoride anion recognition by a doubly strapped porphyrin, Angew. Chem. Int. Ed., 40, 3372-3375 (2001).
246. G. E. Collis, W. M. Campbell, D. L. Officer and A. K. Burrell, The design and synthesis of por-phyrin/oligothiophene hybrid monomers, Org. Biomol. Chem., 3, 2075-2084 (2005).
247. J. Ikemoto, K. Takimiya, Y. Aso, T. Otsubo, M. Fujitsuka and O. Ito, Porphyrin-oligothiophene-fullerene triads as an efficient intramolecular electron-transfer system, Org. Lett., 4, 309-311 (2002).
248. T. Nakamura, J. Ikemoto, M. Fujitsuka, Y. Araki, O. Ito, K. Takimiya, Y. Aso and T. Otsubo, Control of photoinduced energy-and electron-transfer steps in zinc porphyrin-oligothiophene-fullerene linked triads with solvent polarity, J. Phys. Chem B, 109, 14365-14374 (2005).
249. T. Oike, T. Kurata, K. Takimiya, T. Otsubo, Y. Aso, H. Zhang, Y. Araki and O. Ito, Polyether-bridged sexithio-phene as a complexation-gated molecular wire for intramolecular photoinduced electron transfer, J. Am. Chem. Soc., 127, 15372-15373 (2005).
250. H. Higuchi, T. Ishikura, K. Miyabayashi, M. Miyake and K. Yamamoto, Synthesis and properties of orien-tational isomers of hybridized dihexylbithiophene-octaethylporphyrin connected with 1,3-butadiyne linkages, Tetrahedron Lett., 40, 9091-9095 (1999).
251. n-OEP] connected with 1,3-butadiyne linkages, Bull. Chem. Soc. Jpn., 74, 889-906 (2001).
252. N. Hayashi, A. Matsuda, E. Chikamatsu, K. Mori and H. Higuchi, Synthesis and properties of unsymmetrically extended π-electronic conjugation system of octaethylporphyrin(Ni)-dihexybithiophene-octaethylporphyrin(Pd) connected with diacetylene linkage, Tetrahedron Lett., 44, 7155-7158 (2003).
253. 2)] connected with the diacetylene linkage. A methodology for molecular design of the particular electronic structure, Tetrahedron, 60, 6363-6383 (2004).
254. N. Hayashi, A. Naoe, K. Miyabayashi, M. Miyake and H. Higuchi, Synthesis and structural and electronic properties of the octaethylporphyrin-dihexylbithiophene-fullerene derivatives (OEP-DHBTh-C60) connected with diacetylene linkage, Tetrahedron Lett., 46, 6961-6965 (2005).
255. M. A. Sato, M. A. Sakamoto, S. I. Kashiwagi, T. Suzuki and M. Hiroi, Oxidation of ferrocenyl end-substituted oligothiophenes, Bull. Chem. Soc. Jpn., 74, 1737-1742 (2001).
256. S. J. Higgins, L. J. Christopher and S. M. Francis, Synthesis and electropolymerization of 1,1'-bis(5-oligothienyl)ferrocenes: poly(oligothiophene-ferrocene)-modified electrodes, Synth. Met., 98, 211-214 (1999).
257. U. S. Schubert and C. Eschbaumer, Macromolecules containing bipyridine and terpyridine metal complexes: towards metallosupramolecular polymers, Angew. Chem. Int. Ed., 41, 2892-2926 (2002).
258. H. Hofmeier and U. S. Schubert, Recent developments in the supramolecular chemistry of terpyridine-metal complexes, Chem. Soc. Rev., 33, 373-399 (2004).
259. T. M. Pappenfus and K. R. Mann, Synthesis, spectroscopy and electrochemical studies of binuclear tris-bipyridine ruthenium(II) complexes with oligothiophene bridges, Inorg. Chem., 40, 6301-6307 (2001).
260. R. Ziessel, P. Bauerle, M. Ammann, A. Barbieric and F. Barigelletti, Exciton-like energy collection in an oligothiophene wire end-capped by Ru-and Os-polypyridine chromophores, Chem. Commun., 802-804 (2005).
261. P. G. Pickup, Conjugated metallopolymers. Redox polymers with interacting metal based redox sites, J. Mater. Chem., 9, 1641-1653 (1999).
262. M. O. Wolf, Transition-metal-polythiophene hybrid materials, Adv. Mater., 13, 545-553 (2001).
263. M. J. Marsella, R. J. Newland, P. J. Carroll and T. M. Swager, Ionoresistivity as a highly sensitive sensory probe: investigations of polythiophenes functionalized with calix[4]arene-based ion receptors, J. Am. Chem. Soc., 117, 9842-9848 (1995).
264. H.-H. Yu, B. Xu and T. M. Swager, A proton-doped calix[4]arene-based conducting polymer, J. Am. Chem. Soc., 125, 1142-1143 (2003).
265. H.-H. Yu, A. E. Pullen, M. G. Büschel and T. M. Swager, Charge-specific interactions in segmented conducting polymers: an approach to selective ionoresistive responses, Angew. Chem. Int. Ed., 43, 3700-3703 (2004).
266. M. Giannetto, G. Mori, A. Notti, S. Pappalardo and M. F. Parisi, Calixarene-poly(dithiophene)-based chemically modified electrodes, Chem. Eur. J., 7, 3354-3362 (2001).
267. S. Rizzo, F. Sannicolo, T. Benincori, G. Schiavon, S. Zecchin and G. Zotti, Calix[4]arene-functionalized poly-cyclopenta[2,1-b;3,4-b']bithiophenes with good recognition ability and selectivity for small organic molecules for application in QCM-based sensors, J. Mater. Chem., 14, 1804-1811 (2000).
268. A. Vigalok and T. M. Swager, Conducting polymers of tungsten(VI)-oxo calixarene: Intercalation of neutral organic guests, Adv. Mater., 14, 368-371 (2002).
269. X. H. Sun, C. S. Chan, M. S. Wong and W. Y. Wong, Synthesis of tetra-oligothiophene-substituted calix[4]arenes and their optical and electrochemical properties, Tetrahedron, 62, 7846-7853 (2006).
270. P. Bauerle and S. Scheib, Molecular recognition of alkali-ions by crown-ether-functionalized poly(alkylthiophenes), Adv. Mater., 5, 848-853 (1993).
271. S. Scheib and P. Bauerle, Synthesis and characterization of oligo-and crown ether-substituted polythiophenenes-a comparative study, J. Mater. Chem., 9, 2139-2150 (1999).
272. F. Sannicolo, E. Brenna, T. Benincori, G. Zotti, S. Zecchin, G. Schiavon and T. Pilati, Highly ordered poly(cyclopentabithiophenes) functionalized with crown-ether moieties for lithium-and sodium-sensing electrodes, Chem. Mater., 10, 2167-2176 (1998).
273. P. Bauerle and S. Scheib, Synthesis and characterization of thiophenes, oligothiophenes and polythiophenes with crown ether units in direct π-conjugation, Acta Polym., 46, 124-129 (1995).
274. G. Rimmel and P. Bauerle, Molecular recognition properties of crown ether-functionalized oligothiophenes, Synth. Met., 102, 1323-1324 (1999).
275. A. Berlin, G. Zotti, S. Zecchin and G. Schiavon, EQCM analysis of alkali metal ion coordination properties of a novel poly(thiophene)s 3,4-functionalized with crown-ether moieties, Synth. Met., 131, 149-160 (2002).
276. P. Blanchard, L. Huchet, E. Levillain and J. Roncali, Cation template assisted electrosynthesis of a highly π-conjugated polythiophene containing oligooxyethylene segments, Electrochem. Commun., 2, 1-5 (2000).
277. B. Jousselme, P. Blanchard, E. Levillain, J. Delaunay, M. Allain, P. Richomme, D. Rondeau, N. Gallego-Planas and J. Roncali, Crown-annelated oligothiophenes as model compounds for molecular actuation, J. Am. Chem. Soc., 125, 1363-1370 (2003).
278. M. Hiller, C. Kranz, J. Huber, P. Bauerle and W. Schuhmann, Amperometric biosensors produced by immobilization of redox enzymes at polythiophene-modified electrode surfaces, Adv. Mater., 8, 219-222 (1996).
279. K. Faid and M. Leclerc, Responsive supramolecular polythiophene assemblies, J. Am. Chem. Soc., 120, 5274-5278 (1998).
280. H.-A. Ho, M. Boissinot, M. G. Bergeron, G. Corbeil, K. Dore, D. Boudreau and M. Leclerc, Colorimetric and fluorometric detection of nucleic acids using cationic polythiophene derivatives, Angew. Chem. Int. Ed., 41, 1548-1551 (2002).
281. P. Bauerle, M. Hiller, S. Scheib, M. Sokolowski and E. Umbach, Post-polymerization functionalization of conducting polymers: novel poly(alkylthiophene)s substituted with easily replaceable activated ester groups, Adv. Mater., 8, 214-218 (1996).
282. A. Meyer, Modifizierte Elektrodenoberflachen aus funktionalisierten Oligo-und Poly(ethylendioxythiophenen), PhD Thesis, University of Ulm, 2000.
283. A. Emge and P. Bauerle, Synthesis and molecular recognition properties of DNA-and RNA-base-functionalized oligo-and polythiophenes, Synth. Met., 84, 213-214 (1997).
284. P. Bauerle and A. Emge, Specific recognition of nucleobase-functionalized polythiophenes, Adv. Mater., 10, 324-330 (1998).
285. A. Emge and P. Bauerle, Molecular recognition properties of nucleobase-functionalized polythiophenes, Synth. Met., 102, 1370-1373 (1999).
286. G. Barbarella, Oligothiophene isothiocyanates as fluorescent markers, Chem. Eur. J., 8, 5072-5077 (2002).
287. G. Barbarella, M. Zambianchi, O. Pudova, V. Paladini, A. Ventola, F. Cipriani, G. Gigli, R. Cingolani and G. Citro, Oligothiophene isothiocyanates as a new class of fluorescent markers for biopolymers, J. Am. Chem. Soc., 123, 11600-11607 (2001).
288. G. Sotgiu, M. Zambianchi, G. Barbarella, F. Aruffo, F. Cipriani and A. Ventola, Rigid-core fluorescent oligothiophene-S, S-dioxide isothiocyanates. Synthesis, optical characterization and conjugation to monoclonal antibodies, J. Org. Chem., 68, 1512-1520 (2003).
289. H. A. Klok, A. Rosler, G. Götz, E. Mena-Osteritz and P. Bauerle, Synthesis of a silk-inspired peptide-oligothiophene conjugate, Org. Biomol. Chem., 2, 3541-3544 (2004).
290. T. Kirschbaum, C. A. Briehn and P. Bauerle, Efficient solid-phase synthesis of regioregular head-to-tail-coupled oligo(3-a!kylthiophene)s up to a dodecamer, J. Chem. Soc., Perkin Trans. 1, 1211-1216 (2000).
291. T. Kirschbaum and P. Bauerle, Polymer-supported synthesis of regioregular head-to-tail coupled oligo(3-alkylthiophene)s, Synth. Met., 119, 127-128 (2001).
292. C. Strassler, N. E. Davis and E. T. Kool, Novel nucleoside analogues with fluorophores replacing the DNA base, Helv. Chim. Acta, 82, 2160-2171 (1999).
293. K. Kawai, A. Sugimoto, H. Yoshida, S. Tojo, M. Fujitsuka and T. Majima, Synthesis and properties of terthiophene-modified oligodeoxynucleotides, Bioorg. Med. Chem. Lett., 15, 4547-4549 (2005).
294. M. L. Capobianco, M. Naldi, M. Zambianchi and G. Barbarella, Oligothiophene phosphoramidites for oligonucleotide labelling, Tetrahedron Lett., 46, 8181-8184 (2005).
295. G. Barbarella, M. Zambianchi, G. Sotgiu, A. Ventola, M. Galeotti, G. Gigli, A. Cazzato and M. L. Capobianco, Thiophene-based fluorescent markers for the efficient labeling of monoclonal antibodies and oligonucleotides, J. Non-Cryst. Solids, 352, 2465-2467 (2006).
296. G. Barbarella, M. Zambianchi, A. Ventola, E. Fabiano, F. DellaSala, G. Gigli, M. Anni, A. Bolognesi, L. Polito, M. Naldi and M. Capobianco, Bright oligothiophene N-succinimidyl esters for efficient fluorescent labeling of proteins and oligonucleotides, Bioconj. Chem., 17, 58-67 (2006).
297. A. Herland, K. P. R. Nilsson, J. D. M. Olsson, P. Hammarstrom, P. Konradsson and O. Inganas, Synthesis of a regioregular zwitterionic conjugated oligoelectrolyte, usable as an optical probe for detection of amyloid fibril formation at acidic pH, J. Am. Chem. Soc., 127, 2317-2323 (2005).
298. A. Herland, P. Bjork, K. P. R. Nilsson, J. D. M. Olsson, P. Asberg, P. Konradsson, P. Hammarstrom and O. Inganas, Electroactive luminescent self-assembled bio-organic nanowires: integration of semiconducting oligo-electrolytes within amyloidogenic proteins, Adv. Mater., 17, 1466-1471 (2005).
299. F. Mouffouk, S. J. Brown, A. M. Demetriou, S. J. Higgins, R. J. Nichols, R. M. G. Rajapakse and S. Reeman, Electrosynthesis and characterization of biotin-functionalized poly(terthiophene) copolymers and their response to avidin, J. Mater. Chem., 15, 1186-1196 (2005).
300. H. Nakazumi, T. Ohta, H. Etoh, T. Uno, C. L. Colyer, Y. Hyodo and S. Yagi, Near-infrared luminescent bis-squaraine dyes linked by a thiophene or pyrene spacer for noncovalent protein labeling, Synth. Met., 153, 33-36 (2005).
301. E. E. Nesterov, J. Skoch, B. T. Hyman, W. E. Klunk, B. J. Bacskai and T. M. Swager, In vivo optical imaging of amyloid aggregates in brain: design of fluorescent markers, Angew. Chem. Int. Ed., 44, 5452-5456 (2005).
302. M. Kertesz, C. H. Choi and S. Yang, Conjugated polymers and aromaticity, Chem. Rev., 105, 3448-3481 (2005).
303. F. Wudl, M. Kobayashi and A. J. Heeger, Poly(isothianaphthene) J. Org. Chem., 49, 3382-3384 (1984).
304. H. Neugebauer, C. Kvarnstrom, C. Brabec, N. S. Sariciftci, R. Kiebooms, F. Wudl and S. Luzzati, Infrared spectroelectrochemical investigations on the doping of soluble poly(isothianaphthene methine) (PIM), J. Chem. Phys., 110, 12108-12115 (1999).
305. B. L. Lee and T. Yamamoto, Syntheses of new alternating CT-type copolymers of thiophene and pyrido[3,4-b]pyrazine units: their optical and electrochemical properties in comparison with similar CT copolymers of thiophene with pyridine and quinoxaline, Macromolecules, 32, 1375-1382 (1999).
306. M. Kobayashi, J. Chen, T. C. Chung, F. Moraes, A. J. Heeger and F. Wudl, Synthesis and properties of chemically coupled poly(thiophene), Synth. Met., 9, 77-86 (1984).
307. M. Kobayashi, N. Colaneri, M. Boysel, F. Wudl and A. J. Heeger, The electronic and electrochemical properties of poly(isothianaphthene), J. Chem. Phys., 82, 5717-5723 (1985).
308. M. Pomerantz, B. Chaloner-Gill, L. O. Harding, J. J. Tseng and W. J. Pomerantz, New processable low bandgap, conjugated polyheterocycles, Synth. Met., 55, 960-965 (1993).
309. D. L. Vangeneugden, R. H. L. Kiebooms, D. J. M. Vanderzande and J. M. J. V. Gelan, A general synthetic route towards soluble poly(1,3-dithienylisothianaphthene) derivatives, Synth. Met., 101, 120-121 (1999).
310. T.-T. Hung and S.-A. Chen, The synthesis and characterization of soluble poly(isothianaphthene) derivative: poly(5,6-dihexoxyisothianaphthene), Polymer, 40, 3881-3884 (1999).
311. D. Lorcy and M. P. Cava, Poly(isothianaphthene-bithiophene): a new regularly structured polythiophene analogue, Adv. Mater., 4, 562-564 (1992).
312. P. Bauerle, G. Gotz, P. Emele and H. Port, Synthesis and characterization of new annelated terheterocycles, Adv. Mater., 4, 564-568 (1992).
313. S. Musmanni and J. P. Ferraris, Preparation and characterization of conducting polymers based on 1,3-di(2-thienyl)benzo[c]thiophene, J. Chem. Soc., Chem. Commun., 172-174 (1993).
314. R. H. L. Kiebooms, P. J. A. Adriaensens, D. J. M. Vanderzande and J. M. J. V. Gelan, Grignard reactions on ortho dicarboxylic arene derivatives. Synthesis of 1,3-dithienylisothianaphthene compounds, J. Org. Chem., 62, 1473-1480 (1997).
315. U. Mitschke and P. Bauerle, Synthesis, characterization and electrogenerated chemiluminescence of phenyl-substituted, phenyl-annulated and spirofluorenyl-bridged oligothiophenes, J. Chem. Soc., Perkin Trans. 1, 740-753 (2001).
316. G. Grüner, Transition metal π-complexes of benzoanellated oligothiophenes, PhD Thesis, University of Ulm, 2000.
317. P. Bauerle, The synthesis of oligothiophenes, in Handbook of Oligo and Polythiophenes, ed. D. Fichou, Wiley-VCH Verlag GmbH, Weinheim, 1999, pp. 89-181.
318. A. K. Mohanakrishnan, M. V. Lakshmikantham, C. McDougal, M. P. Cava, J. W. Baldwin and R. M. Metzger, Studies in the dithienylbenzo[c]thiophene series, J. Org. Chem., 63, 3105-3112 (1998).
319. Y. Ikenoue, Synthesis and characteristic properties of poly(naphtho)[2,3-c]thiophene) as a series of fused-ring conducting polymers analogous to poly(isothianaphthene), Synth. Met., 35, 263-270 (1990).
320. M. V. Lakshmikantham, D. Lorcy, C. Scordilis-Kelley, X.-L. Wu, J. P. Parakka, R. M. Metzger and M. P. Cava, Poly(naphtho[2,3-c]thiophene-alt-bithiophene): a novel low bandgap polymer, Adv. Mater., 5, 723-726 (1993).
321. D. L. Vangeneugden, D. J. M. Vanderzande, J. Salbeck, P. A. van Hal, R. A. J. Janssen, J. C. Hummelen, C. J. Brabec, S. E. Shaheen and N. S. Sariciftci, Synthesis and characterization of a poly(1,3-dithienylisothiana-phthene) derivative for bulk heterojunction photovoltaic cells, J. Phys. Chem. B, 105, 11106-11113 (2001).
322. R. Kisselev and M. Thelakkat, Synthesis and characterization of poly(triarylamine)s containing isothianaphthene moieties, Macromolecules, 37, 8951-8958 (2004).
323. R. Kisselev and M. Thelakkat, Synthesis of novel 1,3-bis(5-diarylaminothiophen-2-yl)isothianaphthenes, Chem. Commun., 1530-1531 (2002).
324. H. Meng and F. Wudl, A robust low bandgap processable n-type conducting polymer based on poly(isothianaphthene), Macromolecules, 34, 1810-1816 (2001).
325. H. Meng, D. Tucker, S. Chaffins, Y. Chen, R. Helgeson, B. Dunn and F. Wudl, An unusual electrochromic device based on a new low-bandgap conjugated polymer, Adv. Mater., 15, 146-149 (2003).
326. G. Sonmez, H. Meng and F. Wudl, Very stable low bandgap polymer for charge storage purposes and near-infrared applications, Chem. Mater., 15, 4923-4929 (2003).
327. J. P. Ferraris, A. Bravo, W. Kim and D. C. Hrncir, Reduction of steric interactions in thiophene-pyridino[c]thiophene copolymers, J. Chem. Soc., Chem. Commun., 991-992 (1994).
328. M. Pomerantz, B. Chaloner-Gill, L. O. Harding, J. J. Tseng and W. J. Pomerantz, Poly(2,3-dihexylthieno [3,4-b]pyrazine). A new processable low bandgap polyheterocycle, J. Chem. Soc., Chem. Commun., 1672-1673 (1992).
329. J. Kastner, H. Kuzmany, D. Vegh, M. Landl, L. Cuff and M. Kertesz, Raman spectra of poly(2,3-R, R-thieno[3,4-b]pyrazine). A new low-bandgap polymer, Macromolecules, 28, 2922-2929 (1995).
330. J. Armand, C. Bellec, L. Boulares, P. Chaquin, D. Masure and J. Pinson, Electrochemical and chemical reduction of furopyrazines, thienopyrazines, furoquinoxalines and thienoquinoxalines, J. Org. Chem., 56, 4840-4845 (1991).
331. D. D. Kenning, K. A. Mitchell, T. R. Calhoun, M. R. Funfar, D. J. Sattler and S. C. Rasmussen, Thieno[3,4-b]pyrazines: synthesis, structure and reactivity, J. Org. Chem., 67, 9073-9076 (2002).
332. D. D. Kenning and S. C. Rasmussen, A second look at polythieno[3,4-b]pyrazines: chemical vs electrochemical polymerization and its effect on bandgap, Macromolecules, 36, 6298-6299 (2003).
333. C. Kitamura, S. Tanaka and Y. Yamashita, Synthesis of new narrow bandgap polymers based on 5,7-di(2-thienyl)thieno[3,4-b]pyrazine and its derivatives, J. Chem. Soc., Chem. Commun., 1585-1586 (1994).
334. L. M. Campos, A. Tontcheva, S. Günes, G. Sonmez, H. Neugebauer, N. S. Sariciftci and F. Wudl, Extended photocurrent spectrum of a low bandgap polymer in a bulk heterojunction solar cell, Chem. Mater., 17, 4031-4033 (2005).
335. S. Akoudad and J. Roncali, Electrogenerated poly(thiophenes) with extremely narrow bandgap and high stability under n-doping cycling, Chem. Commun., 2081-2082 (1998).
336. I. F. Perepichka, E. Levillain and J. Roncali, Effect of substitution of 3,4-ethylenedioxythiophene (EDOT) on the electronic properties of the derived electrogenerated low bandgap conjugated polymers, J. Mater. Chem., 14, 1679-1681 (2004).
337. A. Berlin, G. Zotti, S. Zecchin, G. Schiavon, B. Vercelli and A. Zanelli, New low-gap polymers from 3,4-ethylenedioxythiophene-bis-substituted electron-poor thiophenes. The roles of thiophene, donor-acceptor alternation and copolymerization in intrinsic conductivity, Chem. Mater., 16, 3667-3676 (2004).
338. J. Casado, R. P. Ortiz, M. C. Ruiz Delgado, V. Hernandez, J. T. Lopez Navarrete, J. M. Raimundo, P. Blanchard, M. Allain and J. Roncali, Alternated quinoid/aromatic units in terthiophenes building blocks for electroactive narrow bandgap polymers. Extended spectroscopic, solid state, electrochemical and theoretical study, J. Phys. Chem. B, 109, 16616-16627 (2005).
339. G. Sonmez, Polymeric electrochromics, Chem. Commun., 5251-5259 (2005).
340. G. Sonmez and F. Wudl, Completion of the three primary colors: the final step toward plastic displays, J. Mater. Chem., 15, 20-22 (2005).
341. G. Sonmez, H. B. Sonmez, C. K. F. Shen, R. W. Jost, Y. Rubin and F. Wudl, A processable green polymeric electrochromic, Macromolecules, 38, 669-675 (2005).
342. G. Sonmez, H. B. Sonmez, C. K. F. Shen and F. Wudl, Red, green and blue colors in polymeric electrochromics, Adv. Mater., 16, 1905-1908 (2004).
343. G. Sonmez, C. K. F. Shen, Y. Rubin and F. Wudl, A red, green and blue (RGB) polymeric electrochromic device (PECD): the dawning of the PECD era, Angew. Chem. Int. Ed., 43, 1498-1502 (2004).
344. M. M. Wienk, M. G. R. Turbiez, M. P. Struijk, M. Fonrodona and R. A. J. Janssen, Low-bandgap poly(di-2-thienylthienopyrazine):fullerene solar cells, Appl. Phys. Lett., 88, 153511(1)-153511(3) (2006).
345. N.-K. Persson, M. Sun, P. Kjellberg, T. Pullerits and O. Inganas, Optical properties of low bandgap alternating copolyfluorenes for photovoltaic devices, J. Chem. Phys., 123, 204718(1)-204718(9) (2005).
346. E. Perzon, X. Wang, F. Zhang, W. Mammo, J. L. Delgado, P. de la Cruz, O. Inganas, F. Langa and M. R. Andersson, Design, synthesis and properties of low bandgap polyfluorenes for photovoltaic devices, Synth. Met., 154, 53-56 (2005).
347. F. Zhang, E. Perzon, X. Wang, W. Mammo, M. R. Andersson and O. Inganas, Polymer solar cells based on a low-bandgap fluorene copolymer and a fullerene derivative with photocurrent extended to 850 nm, Adv. Funct. Mater., 15, 745-750 (2005).
348. F. Zhang, W. Mammo, L. M. Andersson, S. Admassie, M. R. Andersson and O. Inganas, Low-bandgap alternating fluorene copolymer/methanofullerene heterojunctions in efficient near-infrared polymer solar cells, Adv. Mater., 18, 2169-2173 (2006).
349. L. M. Andersson and O. Inganas, Acceptor influence on hole mobility in fullerene blends with alternating copolymers of fluorene, Appl. Phys. Lett., 88, 082103(1)-082103(3) (2006).
350. S. Tanaka and Y. Yamashita, Synthesis of a narrow bandgap heterocyclic polymer: poly-4,6-di(2-thienyl)thieno[3,4-c][1, 2, 5]thiadiazole, Synth. Met., 55, 1251-1254 (1993).
351. S. Tanaka and Y. Yamashita, Syntheses of narrow bandgap heterocyclic copolymers of aromatic-donor and quinonoid-acceptor units, Synth. Met., 69, 599-600 (1995).
352. S. Tanaka and Y. Yamashita, A novel monomer candidate for intrinsically conductive organic polymers based on nonclassical thiophene, Synth. Met., 84, 229-230 (1997).
353. M. C. Ruiz Delgado, V. Hernandez, J. T. Lopez Navarrete, S. Tanaka and Y. Yamashita, Combined spectroscopic and theoretical study of narrow bandgap heterocyclic co-oligomers containing alternating aromatic donor and o-quinoid acceptor units, J. Phys. Chem. B, 108, 2516-2526 (2004).
354. T. Okamoto, K. Kudoh, A. Wakamiya and S. Yamaguchi, General synthesis of extended fused oligothiophenes consisting of an even number of thiophene rings, Chem. Eur. J., 13, 548-556 (2007).
355. n helix: asymmetric synthesis and structure of carbon-sulfur [11]helicene, J. Am. Chem. Soc., 127, 13806-13807 (2005).
356. M. K. Shepherd, Cyclobuta [1,2-c:3,4-c]dithiophene, J. Chem. Soc., Chem. Commun., 880-881 (1985).
357. H. Hart and M. Sasaoka, Exocyclic benzenes. Synthesis and properties of benzo[1,2-c:3,4-c':5,6-c"]trithiophene, a tristhiahexaradialene, J. Am. Chem. Soc., 100, 4326-4327 (1978).
358. N. Jayasuriya, J. Kagan, J. E. Owens, E. P. Kornak and D. M. Perrine, Photocyclization of terthiophenes, J. Org. Chem., 54, 4203-4205 (1989).
359. R. Proetzsch, D. Bieniek and F. Korte, Hochdruckreaktionen IV: Verhalten von Thiolactonen unter hohen Drucken, Tetrahedron Lett., 13, 543-544 (1972).
360. Y. Nicolas, P. Blanchard, E. Levillain, M. Allain, N. Mercier and J. Roncali, Planarized star-shaped oligothio-phenes with enhanced π-electron delocalization, Org. Lett., 6, 273-276 (2004).
361. K. Imamura, K. Takimiya, T. Otsubo and Y. Aso, Triphenyleno[1,12-bcd:4,5-b'c'd':8,9-b"c"d"]trithiophene: the first bowl-shaped heteroaromatic, Chem. Commun., 1859-1860 (1999).
362. T. Kauffmann, B. Greving, J. Konig, A. Mitschker and A. Woltermann, Synthesis of heterocyclic cyclopolyaro-matics containing similar kinds of nuclei, Angew. Chem. Int. Ed. Engl., 14, 713-714 (1975).
363. 4, Acta Crystallogr., Sect. C, 41, 1088-1089 (1985).
364. Z.-H. Zhou and T. Yamamoto, Research on carbon-carbon coupling reactions of haloaromatic compounds mediated by zerovalent nickel complexes. Preparation of cyclic oligomers of thiophene and benzene and stable anthrylnickel(II) complexes, J. Organomet. Chem., 414, 119-127 (1991).
365. T. Kauffmann, From the principle of areno-analogy to heterocyclopolyaromatic compounds, Angew. Chem. Int. Ed. Engl., 18, 1-19 (1979).
366. M. J. Marsella and R. J. Reid, Toward molecular muscles: design and synthesis of an electrically conducting poly[cyclooctatetrathiophene], Macromolecules, 32, 5982-5984 (1999).
367. M. J. Marsella, Classic annulenes, nonclassical applications, Acc. Chem. Res., 35, 944-951 (2002).
368. M. J. Marsella, I. T. Kim and F. Tham, Toward conjugated double helical ladder polymers: cyclooctatetrathio-phene as a highly versatile double helical scaffold, J. Am. Chem. Soc., 122, 974-975 (2000).
369. S. M. H. Kabir, M. Miura, S. Sasaki, G. Harada, Y. Kuwatani, M. Yoshida and M. Iyoda, New syntheses of tricyclic thiophenes and cyclic tetrathiophenes using transition-metal-catalyzed cyclization, Heterocycles, 52, 761-774 (2000).
370. M. J. Marsella, K. Yoon and F. S. Tham, Synthesis and crystal structure of a tubular sexithiophene, Org. Lett., 3, 2129-2131 (2001).
371. A. J. W. Tol, The instability of a bipolaron versus two polarons: charge localization in cyclo-dodecathiophene, Synth. Met., 74, 95-98 (1995).
372. D. Zhao and J. S. Moore, Shape-persistent arylene ethynylene macrocycles: syntheses and supramolecular chemistry, Chem. Commun., 807-818 (2003).
373. C. Grave and A. D. Schlüter, Shape-persistent, nano-sized macrocycles, Eur. J. Org. Chem., 3075-3098 (2002).
374. S. Hoger, Highly efficient methods for the preparation of shape-persistent macrocyclics, J. Polym. Sci. A, Polym. Chem., 37, 2685-2698 (1999).
375. A. De Meijere and S. I. Kozhushkov, Macrocyclic structurally homoconjugated oligoacetylenes: acetylene-and diacetylene-expanded cycloalkanes and rotanes, Top. Curr. Chem., 201, 1-42 (1999).
376. M. M. Haley, J. J. Pak and S. C. Brand, Macrocyclic oligo(phenylacetylenes) and oligo(phenyldiacetylenes), Top. Curr. Chem., 201, 81-130 (1999).
377. J. Kreimer, I. Rios-Carreras, G. Furhmann, C. Müsch, M. Wunderlin, T. Debaerdemacker, E. Mena-Osteritz and P. Bauerle, Synthesis of the first fully α-conjugated macrocyclic oligothiophenes: cyclo[n]thiophenes with tunable cavities in the nanometer regime, Angew. Chem. Int. Ed., 39, 3481-3486 (2000).
378. G. Fuhrmann, J. Kreimer and P. Baurele, Synthesis of macrocyclic oligothiophenes, Synth. Met., 119, 125-126 (2001).
379. G. Fuhrmann, Synthesis and characterization of oligothiophene-based fully π-conjugated macrocycles, PhD Thesis, University of Ulm, 2006.
380. D. M. Perrine and J. Kagan, A side reaction in the synthesis of 2-ethynylthiophene from 2-thiophene-carboxaldehyde by the Corey procedure and an inproved synthesis of 2,2':5',2'-terthiophene, Heterocycles, 24, 365-368 (1986).
381. J. Kromer and P. Bauerle, Homologous series of regioregular alkylsubstituted oligothiophenes up to an 11-mer, Tetrahedron, 57, 3785-3794 (2001).
382. T. Kauffmann, B. Greving, R. Kriegesmann, A. Mitschker and A. Woltermann, Heterocyclopolyaromaten, VI: Heterocyclotetraaromaten mit gleichartigen aromatischen Ringgliedern, Chem. Ber., 111, 1330-1336 (1978).
383. T. Kauffmann and H. P. Mackowiak, Heterocyclopolyaromatics, XIV. 2-Lithio-(all-α S)cyclotetrathiophene: synthesis and preparative applications, Chem. Ber., 118, 2343-2352 (1985).
384. S.-H. Jung, W. Pisula, A. Rouhanipour, H. J. Rader, J. Josemon and K. Müllen, A conjugated polycarbazole ring around a porphyrin, Angew. Chem. Int. Ed., 45, 4685-4690 (2006).
385. G. R. Desiraju, Chemistry beyond the molecule, Nature, 412, 397-400 (2001).
386. H.-J. Schneider and A. Yatsimirsky, Principles and Methods in Supramolecular Chemistry, John Wiley & Sons, Ltd, Chicester, 1999.
387. J. L. Atwood, J. E. D. Davies, D. D. MacNicol and F. Vogtle (eds), Comprehensive Supramolecular Chemistry, Pergamon Press, Oxford, 1996.
388. J.-M. Lehn, Supramolecular Chemistry, VCH Verlag GmbH, Weinheim, 1995.
389. M. Mascal, Noncovalent design principles and the new synthesis, Contemp. Org. Synth., 1, 31-46 (1994).
390. J.-M. Lehn, Supramolecular chemistry: receptors, catalysts and carriers, Science, 227, 849-856 (1985).
391. M. Fujita, Metal-directed self-assembly of two-and three-dimensional synthetic receptors, Chem. Soc. Rev., 27, 417-425 (1998).
392. S. Leininger, B. Olenyuk and P. J. Stang, Self-assembly of discrete cyclic nanostructures mediated by transition metals, Chem. Rev., 100, 853-908 (2000).
393. B. J. Holliday and C. A. Mirkin, Strategies for the construction of supramolecular compounds through coordination chemistry, Angew. Chem. Int. Ed., 40, 2022-2043 (2001).
394. R. Rossi, A. Carpita and C. Bigelli, A palladium-promoted route to 3-alkyl-4-(1-alkynyl)hexa-1,5-diyn-3-enes and/or-1,3-diynes, Tetrahedron Lett., 26, 523-526 (1985).
395. Q. Liu and D. J. Burton, A facile synthesis of diynes, Tetrahedron Lett., 38, 4371-4374 (1997).
396. G. Fuhrmann, T. Debaerdemaeker and P. Bauerle, C-C bond formation through oxidatively induced elimination of platinum complexes-a novel approach towards conjugated macrocycles, Chem. Commun., 948-949 (2003).
397. E. Mena-Osteritz and P. Bauerle, Self-assembled hexagonal nanoarrays of novel macrocyclic oligothiophene-diacetylenes, Adv. Mater., 13, 243-246 (2001).
398. E. Mena-Osteritz, Superstructures of self-organizing thiophenes, Adv. Mater., 14, 609-616 (2002).
399. R. J. O. M. Hoofman, M. P. de Haas, L. D. A. Siebbeles and J. M. Warman, Highly mobile electrons and holes on isolated chains of the semiconducting polymer poly(phenylene vinylene), Nature, 392, 54-56 (1998).
400. H. Sirringhaus, P. J. Brown, R. H. Friend, M. M. Nielsen, K. Bechgaard, B. M. W. Langeveld-Voss, A. J. H. Spiering, R. A. J. Janssen, E. W. Meijer, P. Herwig and D. M. de Leeuw, Two-dimensional charge transport in self-organized, high-mobility conjugated polymers, Nature, 401, 685-688 (1999).
401. H. Engelkamp, S. Middelbeek and R. J. M. Nolte, Self-assembly of disk-shaped molecules to coiled-coil aggregates with tunable helicity, Science, 284, 785-788 (1999).
402. L. F. Chi, S. Jacobi, B. Anczykowski, M. Overs, H. J. Schafer and H. Fuchs, Supermolecular periodic structures in monolayers, Adv. Mater., 12, 25-30 (2000).
403. M. Kolb, G. E. Engelmann and J. C. Ziegler, On the unusual electrochemical stability of nanofabricated copper clusters, Angew. Chem. Int. Ed., 39, 1123-1125 (2000).
404. G. Maruccio, R. Cingolani and R. Rinaldi, Projecting the nanoworld: concepts, results and perspectives of molecular electronics, J. Mater. Chem., 14, 542-554 (2004).
405. M. Bednarz, P. Reineker, E. Mena-Osteritz and P. Bauerle, Optical absorption spectra of linear and cyclic thiophenes-selection rules manifestation, J. Lumin., 110, 225-231 (2004).
406. A. Bhaskar, G. Ramakrishna, K. Hagedorn, O. Varnavski, E. Mena-Osteritz, P. Bauerle and T. Goodson III, Enhancement of two-photon absorption cross-section in macrocyclic thiophenes with cavities in the nanometer regime, J. Phys. Chem. B, 111, 946-954 (2007).
407. S. S. Zade and M. Bendikov, Cyclic oligothiophenes: novel organic materials and models for polythiophene. A theoretical study, J. Org. Chem., 71, 2972-2981 (2006).
408. M. J. Marsella, G. Piao and F. S. Tham, Expanding tetra[2,3-thienylene]-based molecular muscles to larger [4n]annulenes, Synthesis, 9, 1133-1135 (2002).
409. M. J. Marsella, Z. Q. Wang, R. J. Reid and K. Yoon, Synthesis of acetylenic cyclophanes via intramolecular self-assembly: evidence of perfluorophenyl-phenyl quadrupole interactions in the solution state, Org. Lett., 3, 885-887 (2001).
410. D. Solooki, J. D. Bradshaw, C. A. Tessier and W. J. Youngs, Synthesis and characterization of trithienocy-clotriyne (TTC) and its tetracobalt complex. The first example of a dehydroannulene containing thiophene rings, Organometallics, 13, 451-455 (1994).
411. D. Zhang, C. A. Tessier and W. J. Youngs, Synthesis of tris(2,5-dia!kynylthieno)cyclotriynes, tris(4,5-dialkoxyphenyl)cyclotriynes and tetrakis(4,5-dialkoxyphenyl)cyclotetraynes with long-chain alkyl sub-stituents and the nickel and cobalt complexes of tris[4,5-(didodecyloxy)phenyl]cyclotriyne, Chem. Mater., 11, 3050-3057 (1999).
412. W. J. Youngs, C. A. Tessier and J. D. Bradshaw, ortho-Arene cyclynes, related heterocyclynes and their metal chemistry, Chem. Rev., 99, 3153-3180 (1999).
413. A. Sarkar and M. M. Haley, Synthesis and characterization of dehydrothieno[18]annulenes, Chem. Commun., 1733-1734 (2000).
414. J. R. Nitschke and T. D. Tilley, Convenient, zirconocene-coupling routes to germole-and thiophene-containing macrocycles with triangular geometries, J. Organomet. Chem., 666, 15-22 (2003).
415. I. Jung, H. Choi, E. Kim, C.-H. Lee, S. O. Kang and J. Ko, Synthesis and photochromic reactivity of macro-molecules incorporating four dithienylethene units, Tetrahedron, 61, 12256-12263 (2005).
416. G. M. Badger, J. A. Elix and G. E. Lewis, The synthesis of [18]annulene trisulphide, Aust. J. Chem., 18, 70-89 (1965).
417. Z. Hu, J. L. Atwood and M. P. Cava, A simple route to sulfur bridged annulenes, J. Org. Chem., 59, 8071-8075 (1994).
418. F. Ellinger, A. Gieren, T. Hübner, J. Lex, F. Lucchesini, A. Merz, R. Neidlein and J. Salbeck, Ein Beitrag zum Tetrathiaporphycen-Redoxsystem: Elektrochemische Reduktion eines 20π-Cyclophans zum diatropen 22π-Dianion, Monatsh. Chem., 124, 931-943 (1993).
419. Z. Hu, C. Scordilis-Kelley and M. P. Cava, New thiophene-derived 28-π annulenes, Tetrahedron Lett., 34, 1879-1882 (1993).
420. T. Kawase, H. R. Darabi, R. Uchimiya and M. Oda, Synthesis of 5,6,17,18-bisdehydrotetrathia[24]annulene [2.2.2.2]. A strained planar annulene devoid of peripheral conjugation, Chem. Lett., 24, 499-500 (1995).
421. H. Kurata, H. Baba and M. Oda, 5,8,17,20-Tetrakis(3,5-di-f-butylphenyl)-6,7,18,19-tetradehydrotetrathia[24] annulene-(4.0.4.0) and its dianion: new thiophene-derived paratropic and diatropic annulenes, Chem. Lett., 26, 571-572 (1997).
422. K. Nakao, M. Nishimura, T. Tamachi, Y. Kuwatani, H. Miyasaka, T. Nishinaga and M. Iyoda, Giant macrocycles composed of thiophene, acetylene and ethylene building blocks, J. Am. Chem. Soc., 128, 16740-16747 (2006).
423. Y. Tobe, N. Utsumi, A. Nagano, M. Sonoda and K. Naemura, Synthesis of butadiyne-bridged [4n] metacyclo-phanes having exo-annular t-butyl groups, Tetrahedron, 57, 8075-8083 (2001).
424. O. Meth-Cohn and H. Jiang, Ligands containing alternating 2,6-linked pyridine and 2,5-linked thiophene units, J. Chem. Soc., Perkin Trans. 1, 3737-3746 (1998).
425. M. Mayor and C. Didschies, A giant conjugated molecular ring, Angew. Chem. Int. Ed., 42, 3176-3179 (2003).
426. M. Ammann and P. Bauerle, Synthesis and electronic properties of series of oligothiophene-[1, 10]phenanthrolines, Org. Biomol. Chem., 3, 4143-4152 (2005).
427. P. Bauerle, M. Ammann, M. Wilde, G. Gotz, E. Mena-Osteritz, A. Rang and C. A. Schalley, Oligothiophene-based catenanes: synthesis and electronic properties of a novel conjugated topological structure, Angew. Chem. Int. Ed., 46, 363-368 (2007).
428. S. Fomine and P. Guadarrama, Oligothiophene catenanes and knots: a theoretical study, J. Phys. Chem. A, 110, 10098-10105 (2006).
429. G. M. Badger, G. E. Lewis and U. P. Singh, The synthesis of [18]annulene 1,4:7,10-dioxide-13,16-sulphide, Aust. J. Chem., 19, 1461-1476 (1966).
430. G. M. Badger, G. E. Lewis and U. P. Singh, The synthesis of 1,4-epimino[18]annulene 7,10:13,16-disulphide, Aust. J. Chem., 20, 1635-1642 (1967).
431. M. R. Johnson, D. C. Miller, K. Bush, J. J. Becker and J. A. Ibers, Synthesis and characterization of a new 26π-aromatic thiophene-containing macrocyclic ligand, J. Org. Chem., 57, 4414-4417 (1992).
432. G. De Munno, F. Lucchesini and R. Neidlein, 21,23-Dithiaporphycene: the first aromatic sulfur-containing system with porphycene structure, Tetrahedron, 49, 6863-6872 (1993).
433. M. Kozaki, J. P. Parakka and M. P. Cava, New thiophene-pyrrole-derived annulenes containing 6 and 10 heterocyclic units, J. Org. Chem., 61, 3657-3661 (1996).
434. E. Vogel, P. Röhrig, M. Sicken, B. Knipp, A. Herrmann, M. Pohl, H. Schmickler and J. Lex, The thiophene analogue of porphyrin: tetrathiaporphyrin dication, Angew. Chem. Int. Ed. Engl., 28, 1651-1655 (1989).
435. E. Vogel, M. Pohl, A. Herrmann, T. Wiss, C. Konig, J. Lex, M. Gross and J. P. Gisselbrecht, Porphyrinoid macrocycles based on thiophene-the octaethyltetrathiaporphyrin dication, Angew. Chem. Int. Ed. Engl., 35, 1520-1524 (1996).
436. Z. Hu and M. P. Cava, Tetrathia[22]annulene [2, 1, 2, 1]. A new thiophene-derived aromatic macrocycle, Tetrahedron Lett., 35, 34933496 (1994).
437. L. Latos-Grazynski, J. Lisowski, L. Szterenberg, M. M. Olmstead and A. L. Balch, Crystal and molecular structure of 21-thia-5,20-diphenyl-10,15-bis(_p-nitrophenyl)porphyrin and 21,23-dithiatetraphenylporphyrin. The influence of sulfur on the π-delocalization pattern, J. Org. Chem., 56, 4043-4045 (1991).
438. K. Rachlewicz, N. Sprutta, P. J. Chmielewski and L. Latos-Grazynski, Characterization of new 26,28-dihetero sapphyrins: 5,10,15,20-tetraphenyl-26,28-dioxa sapphyrin and 5,10,15,20-tetraphenyl-26,28-dithia sapphyrin, J. Chem. Soc., Perkin Trans. 2, 969-976 (1998).
439. A. Srinivasan, V. G. Anand, S. J. Narayanan, S. K. Pushpan, M. R. Kumar, T. K. Chandrashekar, K.-I. Sugiura and Y. Sakata, Structural characterization of meso aryl sapphyrins, J. Org. Chem., 64, 8693-8697 (1999).
440. S. J. Narayanan, B. Sridevi, T. K. Chandrashekar, A. Vij and R. Roy, Novel core-modified expanded porphyrins with meso-aryl substituents: synthesis, spectral and structural characterization, J. Am. Chem. Soc., 121, 9053-9068 (1999).
441. V. G. Anand, S. K. Pushpan, S. Venkatraman, S. J. Narayanan, A. Dey, T. K. Chandrashekar, R. Roy, B. S. Joshi, S. Deepa and G. N. Sastry, 30π Aromatic meso-substituted heptaphyrin isomers: syntheses, characterization and spectroscopic studies, J. Org. Chem., 67, 6309-6319 (2002).
442. V. R. G. Anand, S. K. Pushpan, A. Srinivasan, S. J. Narayanan, B. Sridevi, T. K. Chandrashekar, R. Roy and B. S. Joshi, Meso aryl heptaphyrins: the first 30π aromatic expanded porphyrins with an inverted structure, Org. Lett., 2, 3829-3832 (2000).
443. V. G. Anand, S. K. Pushpan, S. Venkatraman, A. Dey, T. K. Chandrashekar, B. S. Joshi, R. Roy, W. Teng and K. R. Senge, 34π Octaphyrin: first structural characterization of a planar, aromatic [1.0.1.0.1.0.1.0] octaphyrin with inverted heterocyclic rings, J. Am. Chem. Soc., 123, 8620-8621 (2001).
444. N. Sprutta and L. Latos-Grazynski, Figure-eight tetrathiaoctaphyrin and dihydrotetrathiaoctaphyrin, Chem. Eur. J., 7, 5099-5112 (2001).
445. D. Seidel, V. Lynch and J. L. Sessler, Cyclo[8]pyrrole: a simple-to-make expanded porphyrin with no meso bridges, Angew. Chem. Int. Ed., 41, 14221425 (2002).
446. P. J. Flory, Molecular size distribution in three-dimensional polymers. II. Trifunctional branching units, J. Am. Chem. Soc., 63, 3091-3096 (1941).
447. P. J. Flory, Molecular size distribution in three-dimensional polymers. III. Tetrafunctional branching units, J. Am. Chem. Soc., 63, 3096-3100 (1941).
448. P. J. Flory, Molecular size distribution in three-dimensional polymers. IV. Branched polymers containing A-R-Bf-1 type units, J. Am. Chem. Soc., 74, 2718-2723 (1952).
449. E. Buhleier, W. Wehner and F. Vogtle, 'Cascade' and 'nonskid-chain-like' syntheses of molecular cavity topologies, Synthesis, 155-158 (1978).
450. D. A. Tomalia, H. Baker, J. Dewald, M. Hall, G. Kallos, S. Martin, J. Roeck, J. Ryder and P. Smith, A new class of polymers: starburst-dendritic macromolecules, Polym. J., 17, 117-132 (1985).
451. G. R. Newkome, Z. Yao, G. R. Baker and V. K. Gupta, Cascade molecules: a new approach to micelles. A [27]-arborol, J. Org. Chem., 50, 2003-2004 (1985).
452. G. R. Newkome, C. N. Moorefield and F. Vogtle, Dendrimers and Dendrons: Concepts, Syntheses, Applications, Wiley-VCH Verlag GmbH, Weinheim, 2001.
453. C. N. Moorefield, G. R. Newkome and A. Mishra, Dendrimers, in Encyclopedia of Supramolecular Chemistry, ed. J. L. Atwood and J. W. Steed, Marcel Dekker, New York, 2004, pp. 432-440.
454. J. S. Moore, Shape-persistent molecular architectures of nanoscale dimension, Acc. Chem. Res., 30, 402-413 (1997).
455. L. Gong, Q. Hu and L. Pu, Optically active dendrimers with a binaphthyl core and phenylene dendrons: light harvesting and enantioselective fluorescent sensing, J. Org. Chem., 66, 2358-2367 (2001).
456. S. K. Dev, T. M. Maddux and L. Yu, A simple orthogonal approach to poly-(phenylenevinylene) dendrimers, J. Am. Chem. Soc., 119, 9079-9080 (1997).
457. A. J. Berresheim, M. Müller and K. Müllen, Polyphenylene nanostructures, Chem. Rev., 99, 1747-1785 (1999).
458. Y. Geng, A. Fechtenkotter and K. Müllen, Star-like substituted hexaarylbenzenes: synthesis and mesomorphic properties, J. Mater. Chem., 11, 1634-1641 (2001).
459. A. Bilge, A. Zen, M. Forster, H. Li, F. Galbrecht, B. S. Nehls, T. Farrell, D. Neher and U. Scherf, Swivel-cruciform oligothiophene dimers, J. Mater. Chem., 16, 3177-3182 (2006).
460. A. Zen, A. Bilge, F. Galbrecht, R. Alle, K. Meerholz, J. Grenzer, D. Neher, U. Scherf and T. Farrell, Solution processable organic field-effect transistors utilizing an α,α'-dihexylpentathiophene-based swivel cruciform, J. Am. Chem. Soc., 128, 3914-3915 (2006).
461. X. Sun, Y. Liu, S. Chen, W. Qiu, G. Yu, Y. Ma, T. Qi, H. Zhang, X. Xu and D. Zhu, X-shaped electroactive molecular materials based on oligothiophene architectures: facile synthesis and photophysical and electrochemical properties, Adv. Funct. Mater., 16, 917-925 (2006).
462. X. Sun, Y. Zhou, W. Wu, Y. Liu, W. Tian, G. Yu, W. Qiu, S. Chen and D. Zhu, X-shaped oligothiophenes as a new class of electron donors for bulk-heterojunction solar cells, J. Phys. Chem. B, 110, 7702-7707 (2006).
463. T. M. Pappenfus and K. R. Mann, Synthesis and characterization of radial oligothiophenes: a new class of thiophene-based conjugated homologues, Org. Lett., 4, 3043-3046 (2002).
464. J. Casado, T. M. Pappenfus, K. R. Mann, V. Hernandez and J. T. Lopez Navarrete, Exploration of the electronic structure of dendrimer-like acetylene-bridged oligothiophenes by correlating Raman spectroscopy, electrochemistry and theory, J. Chem. Phys., 120, 11874-11881 (2004).
465. R. De Bettignies, Y. Nicolas, P. Blanchard, E. Levillain, J.-M. Nunzi and J. Roncali, Planarized star-shaped oligothiophenes as a new class of organic semiconductors for heterojunction solar cells, Adv. Mater., 15, 1939-1943 (2003).
466. A. Cravino, S. Roquet, O. Aleveque, P. Leriche, P. Frere and J. Roncali, Triphenylamine-oligothiophene conjugated systems as organic semiconductors for opto-electronics, Chem. Mater., 18, 2584-2590 (2006).
467. I. Tabakovic, Y. Kunugi, A. Canavesi and L. L. Miller, Thienyl triarylamines. Reactivity and spectra of cation radicals and dications, Acta Chem. Scand., 52, 131-136 (1998).
468. K. Yamamoto, M. Higuchi, K. Uchida and Y. Kojima, Synthesis and electrochemical properties of oligo-and poly(thienylphenylamine)s, Macromolecules, 35, 5782-5788 (2002).
469. H. Ohishi, M. Tanaka, H. Kageyama and Y. Shirota, Amorphous molecular materials with high carrier mobilities: thiophene-and selenophene-containing tris(oligoarylenyl)amines, Chem. Lett., 33, 1266-1267 (2004).
470. Y. Kunugi, I. Tabakovic, A. Canavesi and L. L. Miller, Light-emitting diodes based on linear and starburst electro-oligomerized thienyltriphenylamines, Synth. Met., 89, 227-229 (1997).
471. Y. Kunugi, Y. Niwa, L. Zhu, Y. Harima and K. Yamashita, Low operating voltage bilayer organic light-emitting diodes using electrochemically synthesized and p-doped starbust-polymer as hole transporting layer, Chem. Lett., 30, 656-657 (2001).
472. K. Yamamoto, M. Higuchi, K. Uchida and Y. Kojima, Excellent redox properties of poly(thienylphenylamine)s, Macromol. Rapid Commun., 22, 266-270 (2001).
473. J.-S. Cho, Y. Kojima and K. Yamamoto, A novel oligothiophene derivative as a hole-transport with emitting material for OLED, Polym. Adv. Technol., 14, 52-57 (2003).
474. S. Roquet, A. Cravino, P. Leriche, A. O., P. Fröre and J. Roncali, Triphenylamine-thienylenevinylene hybrid systems with internal charge transfer as donor materials for heterojunction solar cells, J. Am. Chem. Soc., 128, 3459-3466 (2006).
475. A. Cravino, P. Leriche, O. Aleveque, S. Roquet and J. Roncali, Light-emitting organic solar cells based on a 3D conjugated system with internal charge transfer, Adv. Mater., 18, 3033-3037 (2006).
476. J. Pei, J. L. Wang, X. Y. Cao, X. H. Zhou and W. B. Zhang, Star-shaped polycyclic aromatics based on oligothiophene-functionalized truxene: synthesis, properties and facile emissive wavelength tuning, J. Am. Chem. Soc., 125, 9944-9945 (2003).
477. Y. M. Sun, K. Y. Q. L. J. L. W. Xiao, J. Pei, G. Yu and D. B. Zhu, Oligothiophene-functionalized truxene: star-shaped compounds for organic field-effect transistors, Adv. Funct. Mater., 15, 818-822 (2005).
478. J. L. Wang, J. Luo, L. H. Liu, Q. F. Zhou, Y. Ma and J. Pei, Nanosized gradient π-conjugated thienylethynylene dendrimers for light harvesting: synthesis and properties, Org. Lett., 8, 2281-2284 (2006).
479. H. Wang, J.-L. Wang, S.-C. Yuan, P. Jian and W.-W. Pei, Novel highly fluorescent dendritic chiral amines: synthesis and optical properties, Tetrahedron, 61, 8465-8474 (2005).
480. J. L. Wang, X. F. Duan, B. Jiang, L. B. Gan, J. Pei, C. He and Y. F. Li, Nanosized rigid π-conjugated molecular heterojunctions with multi [60]fullerenes: facile synthesis and photophysical properties, J. Org. Chem., 71, 4400-4410 (2006).
481. C. C. You, C. R. Saha-Moller and F. Würthner, Synthesis and electropolymerization of novel oligothiophene-functionalized perylene bisimides, Chem. Commun., 2030-2031 (2004).
482. L. X. Chen, S. Xiao and L. Yu, Dynamics of photoinduced electron transfer in a molecular donor-acceptor quartet, J. Phys. Chem. B, 110, 11730-11738 (2006).
483. J. Cremer and P. Bauerle, Star-shaped perylene-oligothiophene-triphenylamine hybrid systems for photovoltaic applications, J. Mater. Chem., 16, 874-884 (2006).
484. A. Petrella, J. Cremer, L. De Cola, P. Bauerle and R. M. Williams, Charge transfer processes in conjugated triarylamine-oligothiophene-perylenemonoimide dendrimers, J. Phys. Chem. A, 109, 11687-11695 (2005).
485. P. Arsenyan, O. Pudova, J. Popelis and E. Lukevics, Novel radial oligothienyl silanes Tetrahedron Lett., 45, 3109-3111 (2004).
486. S. Roquet, R. de Bettignies, P. Leriche, A. Cravino and J. Roncali, Three-dimensional tetra(oligothienyl)silanes as donor material for organic solar cells, J. Mater. Chem., 16, 3040-3045 (2006).
487. 6i blends, Appl. Phys. Lett., 87, 083506(1)-083506(3) (2005).
488. V. D. Mihailetchi, H. X. Xie, B. de Boer, L. J. A. Koster and P. W. M. Blom, Charge transport and photocurrent generation in poly(3-hexylthiophene): methanofullerene bulk-heterojunction solar cells, Adv. Funct. Mater., 16, 699-708 (2006).
489. Y. Kim, S. Cook, S. M. Tuladhar, S. A. Choulis, J. Nelson, J. R. Durrant, D. D. C. Bradley, M. Giles, I. McCulloch, C.-S. Ha and M. Ree, A strong regioregularity effect in self-organizing conjugated polymer films and high-efficiency polythiophene:fullerene solar cells, Nat. Mater., 5, 197-203 (2006).
490. J. Y. Kim, K. Lee, N. E. Coates, D. Moses, T.-Q. Nguyen, M. Dante and A. J. Heeger, Efficient tandem polymer solar cells fabricated by all-solution processing, Science, 317, 222-225 (2007).
491. X.-M. Liu, C. He and J. Huang, A water-soluble non-aggregating fluorescent octa-carboxylic acid derived from tetraphenylmethane: synthesis and optical properties, Tetrahedron Lett., 45, 6173-6177 (2004).
492. X.-M. Liu, C. He and J.-W. Xu, Synthesis and optical properties of tetraphenylmethane-based tetrahedral fluorescent compounds and their water-soluble PEG-linked polymers, Tetrahedron Lett., 45, 1593-1597 (2004).
493. R. Wu, J. S. Schümm, D. L. Pearson and J. M. Tour, Convergent synthetic routes to orthogonally fused conjugated oligomers directed toward molecular scale electronic device applications, J. Org. Chem., 61, 6906-6921 (1996).
494. J. M. Tour, Conjugated macromolecules of precise length and constitution. Organic synthesis for the construction of nanoarchitectures, Chem. Rev., 96, 537-553 (1996).
495. J. Pei, J. Ni, X. H. Zhou, X. Y. Cao and Y. H. Lai, Head-to-tail regioregular oligothiophene-functionalized 9,9'-spirobifluorene derivatives. 1. Synthesis, J. Org. Chem., 67, 4924-4936 (2002).
496. J. Pei, J. Ni, X. H. Zhou, X. Y. Cao and Y. H. Lai, Regioregular head-to-tail oligothiophene-functionalized 9,9'-spirobifluorene derivatives. 2. NMR characterization, thermal behaviors and electrochemical properties, J. Org. Chem., 67, 8104-8113 (2002).
497. S. A. Ponomarenko, E. A. Tatarinova, A. M. Muzafarov, S. Kirchmeyer, L. Brassat, A. Mourran, M. Moeller, S. Setayesh and D. de Leeuw, Star-shaped oligothiophenes for solution-processible organic electronics: flexible aliphatic spacers approach, Chem. Mater., 18, 4101-4108 (2006).
498. L. L. Miller, Y. Kunugi, A. Canavesi, S. Rigaut, C. N. Moorefield and G. R. Newkome, 'Vapoconductivity'. Sorption of organic vapors causes large increases in the conductivity of a dendrimer, Chem. Mater., 10, 1751-1754 (1998).
499. S. Deng, J. Locklin, D. Patton, A. Baba and R. C. Advincula, Thiophene dendron jacketed poly(amidoamine) dendrimers: nanoparticle synthesis and adsorption on graphite, J. Am. Chem. Soc., 127, 1744-1751 (2005).
500. R. C. Advincula, Hybrid organic-inorganic nanomaterials based on polythiophene dendronized nanoparticles, Dalton Trans., 2778-2784 (2006).
501. W. U. Huynh, J. J. Dittmer and A. P. Alivisatos, Hybrid nanorod-polymer solar cells, Science, 295, 2425-2427 (2002).
502. S. A. Ponomarenko, S. Kirchmeyer, A. Elschner, B. H. Huisman, A. Karbach and D. Drechsler, Star-shaped oligothiophenes for solution-processible organic field-effect transistors, Adv. Funct. Mater., 13, 591-596 (2003).
503. S. Ponomarenko and S. Kirchmeyer, Organic compounds having a core-shell structure, US Patent 7 078 724, 2006.
504. C. Xia, X. Fan, J. Locklin and R. C. Advincula, A first synthesis of thiophene dendrimers, Org. Lett., 4, 2067-2070 (2002).
505. W. J. Mitchell, N. Kopidakis, G. Rumbles, D. S. Ginley and S. E. Shaheen, The synthesis and properties of solution processable phenyl cored thiophene dendrimers, J. Mater. Chem., 15, 4518-4528 (2005).
506. N. Kopidakis, W. J. Mitchell, J. Van de Lagemaat, D. S. Ginley, G. Rumbles, S. E. Shaheen and W. L. Rance, Bulk heterojunction organic photovoltaic devices based on phenyl-cored thiophene dendrimers, Appl. Phys. Lett., 89, 103524(1)-103524(3) (2006).
507. H. John, R. Bauer, P. Espindola, P. Sonar, J. Heinze and K. Müllen, 3D-hybrid networks with controllable electrical conductivity from the electrochemical deposition of terthiophene-functionalized polyphenylene dendrimers, Angew. Chem. Int. Ed., 44, 2447-2451 (2005).
508. P. R. L. Malenfant, L. Groenendaal and J. M. J. Fréchet, Well-defined triblock hybrid dendrimers based on lengthy oligothiophene cores and poly(benzyl ether) dendrons, J. Am. Chem. Soc., 120, 10990-10991 (1998).
509. J. J. Apperloo, R. A. J. Janssen, P. R. L. Malenfant, L. Groenendaal and J. M. J. Frechet, Redox states of well-defined π-conjugated oligothiophenes functionalized with poly(benzyl ether) dendrons, J. Am. Chem. Soc., 122, 7042-7051 (2000).
510. J. A. E. H. Van Haare, E. E. Havinga, J. L. J. Van Dongen, R. A. J. Janssen, J. Cornil and J.-L. Bredas, Redox states of long oligothiophenes: two polarons on a single chain, Chem. Eur. J., 4, 1509-1522 (1998).
511. P. R. L. Malenfant, M. Jayaraman and J. M. J. Frechet, Dendrimer-supported oligothiophene synthesis: aliphatic ether dendrimers in the preparation of oligothiophenes with minimal substitution, Chem. Mater., 11, 3420-3422 (1999).
512. A. Adronov, P. R. L. Malenfant and J. M. J. Frechet, Synthesis and steady-state photophysical properties of dye-labeled dendrimers having novel oligothiophene cores: a comparative study, Chem. Mater., 12, 1463-1472 (2000).
513. A. W. Freeman, S. C. Koene, P. R. L. Malenfant, M. E. Thompson and J. M. J. Frechet, Dendrimer-containing light-emitting diodes: toward site-isolation of chromophores, J. Am. Chem. Soc., 122, 12385-12386 (2000).
514. C. Xia, X. Fan, J. Locklin, R. C. Advincula, A. Gies and W. Nonidez, Characterization, supramolecular assembly and nanostructures of thiophene dendrimers, J. Am. Chem. Soc., 126, 8735-8743 (2004).
515. C. Q. Ma, E. Mena-Osteritz, T. Debaerdemaeker, M. M. Wienk, R. A. Janssen and P. Bauerle, Functionalized 3D oligothiophene dendrons and dendrimers-novel macromolecules for organic electronics, Angew. Chem. Int. Ed., 46, 1679-1683 (2007).
516. Y. Z. Su, J. T. Lin, Y.-T. Tao, C.-W. Ko, S.-C. Lin and S.-S. Sun, Amorphous 2,3-substituted thiophenes: potential electroluminescent materials, Chem. Mater., 14, 1884-1890 (2002).
517. Y. Zhang, C. Zhao, J. Yang, M. Kapiamba, O. Haze, L. J. Rothberg and M. K. Ng, Synthesis, optical and electrochemical properties of a new family of dendritic oligothiophenes, J. Org. Chem., 71, 9475-9483 (2006).
518. N. Negishi, Y. Ie, M. Taniguchi, T. Kawai, H. Tada, T. Kaneda and Y. Aso, Synthesis of dendritic oligothiophenes and their self-association properties by intermolecular π-π interactions, Org. Lett., 9, 829-832 (2007).