Fused Oligothiophenes

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

Volumn , Issue , 2009, Pages 219-254

  Skabara, Peter J ^a  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

Author keywords

Cyclic and helical fused oligothiophenes; Dithienothiophene structural isomers; Fused oligothiophenes; Linked bithiophenes; New copolymers based on an alternating cyclopentadithiophene benzothiadiazole structure; Organic field effect transistors (OFETs); Thienothiophene structural isomers; Thiophene based derivatives as organic semiconductor materials

Indexed keywords

EID: 84890689509     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470745533.ch3     Document Type: Chapter

References (147)

1. G. Subramanian, P. v. R. Schleyer and H. Jiao, Are the most stable fused heterobicycles the most aromatic?, Angew. Chem. Int. Ed. Engl., 35, 2638-2641 (1996).
2. T. M. Krygowski and M. K. Cyranski, Structural aspects of aromaticity, Chem. Rev., 101, 1385-1419 (2001).
3. R. Gleiter, R. Bartetzko, G. Brahler and H. Bock, Electronic-structure of sulfur-compounds. 28. Electronic-structure of tetraphenylthieno[3,4-c]thiophene-photoelectron, electron-spin resonance and electronic absorption-spectra, J. Org. Chem., 43, 3893-3897 (1978).
4. C. Muller, A. Schweig, M. P. Cava and M. V. Lakshmikantham, Theory and application of photoelectron-spectroscopy. 69. Thieno[3,4-c]thiophenes-electronic structure, J. Am. Chem. Soc., 98, 7187-7189 (1976).
5. J. I. Aihara, Arornaticity and stability of furofurans and thienothiophenes, J. Phys. Org. Chem., 18, 235-239 (2005).
6. J. Nakayama, A. Ishii, Y. Kobayashi and M. Hoshino, Generation and characterization of the parent 2-lambda-4-delta-2-thieno[3,4-c]thiophene, J. Chem. Soc., Chem. Commun., 959-960 (1988).
7. M. P. Cava and G. E. M. Husbands, Tetraphenylthieno[3,4-c]thiophene. A stable nonclassical thiophene, J. Am. Chem. Soc., 91, 3952-3953 (1969).
8. A. Ishii, J. Nakayama, J. Kazami, Y. Ida, T. Nakamura and M. Hoshino, Synthesis and reactions of 1,3,4,6-tetra-2-thienylthieno[3,4-c]thiophene, J. Org. Chem., 56, 78-82 (1991).
9. S. Yoneda, K. Ozaki, A. Tsubouchi, H. Kojima and K. Yanagi, Tetrakis(alkylthio)thieno[3,4-c]thiophene-synthesis, stability and reactivity, J. Heterocycl. Chem., 25, 559-563 (1988).
10. S. Yoneda, K. Ozaki, T. Inoue, A. Sugimoto, K. Yanagi and M. Minobe, Novel dimerization reaction of bis(alkylthio)cyclopropenethiones affording tetrakis(alkylthio)thieno[3,4-c]thiophenes, J. Am. Chem. Soc., 107, 5801-5802 (1985).
11. N. Beye and M. P. Cava, Synthesis of the first thieno[3,4-c]thiophene stabilized only by electronic effects, J. Org. Chem., 59, 2223-2226 (1994).
12. R. R. Amaresh, M. V. Lakshmikantham, R. X. Geng and M. P. Cava, Thieno[3,4-c]thiophenes: novel synthesis of 1,3-dicarbomethoxy-4,6-dicyanothieno[3,4-c]thiophene, Tetrahedron Lett., 41, 8843-8845 (2000).
13. A. Comel, G. Sommen and G. Kirsch, Thienothiophenes: synthesis and applications, Mini-Rev. Org. Chem., 1, 367-374 (2004).
14. H. Wynberg and D. J. Zwanenburg, Thieno[3,4-b]thiophene. Third thiophthene, Tetrahedron Lett., 761-764 (1967).
15. L. Brandsma and H. D. Verkruijsse, An alternative synthesis of thieno[3,4-b]thiophene, Synth. Commun., 20, 2275-2277 (1990).
16. G. A. Sotzing and K. H. Lee, Poly(thieno[3,4-b]thiophene): a p-and n-dopable polythiophene exhibiting high optical transparency in the semiconducting state, Macromolecules, 35, 7281-7286 (2002).
17. L. S. Fuller, B. Iddon and K. A. Smith, Thienothiophenes. 2. Synthesis, metallation and bromines lithium exchange reactions of thieno[3,2-b]thiophene and its polybromo derivatives, J. Chem. Soc., Perkin Trans. 1, 3465-3470 (1997).
18. D. R. Rutherford, J. K. Stille, C. M. Elliott and V. R. Reichert, Poly(2,5-ethynylenethiophenediylethynylenes), related heteroaromatic analogs and poly(thieno[3,2-b]thiophenes)-synthesis and thermal and electrical properties, Macromolecules, 25, 2294-2306 (1992).
19. S. Gronowitz and B. Persson, A convenient synthesis of thieno[2,3-b]thiophene, Acta Chem. Scand., 21, 812-813 (1967).
20. T. Otsubo, Y. Kono, N. Hozo, H. Miyamoto, Y. Aso, F. Ogura, T. Tanaka and M. Sawada, Syntheses, structures and properties of 2,3,6,7-tetrathiabenzo[1,3-cd:4,6-c'd']dipentalene and its methyl, ethyl, methylthio and ethylthio derivatives-novel fused polynuclear heteroarenes, Bull. Chem. Soc. Jpn., 66, 2033-2041 (1993).
21. R. L. P. de Jong and L. Brandsma, Synthesis of condensed bicyclic thiophene derivatives from diyne systems, J. Chem. Soc., Chem. Commun., 1056-1057 (1983).
22. K. Lee and G. A. Sotzing, Poly(thieno[3,4-b]thiophene). A new stable low bandgap conducting polymer, Macromolecules, 34, 5746-5747 (2001).
23. A. Kumar, Z. Buyukmumcu and G. A. Sotzing, Poly(thieno[3,4-b]furan). A new low bandgap conjugated polymer, Macromolecules, 39, 2723-2725 (2006).
24. B. Lee, M. S. Yavuz and G. A. Sotzing, Poly(thieno[3,4-b]thiophene)s from three symmetrical thieno[3,4-b]thiophene dimers, Macromolecules, 39, 3118-3124 (2006).
25. B. Lee, V. Seshadri, H. Palko and G. A. Sotzing, Ring-sulfonated poly(thienothiophene), Adv. Mater., 17, 1792-1795 (2005).
26. B. Lee, V. Seshadri and G. A. Sotzing, Poly(thieno[3,4-b]thiophene)-poly(styrene sulfonate): a low bandgap, water dispersible conjugated polymer, Langmuir, 21, 10797-10802 (2005).
27. B. Lee, V. Seshadri and G. A. Sotzing, Water dispersible low bandgap conductive polymer based on thieno[3,4-b]thiophene, Synth. Met., 152, 177-180 (2005).
28. V. Seshadri, L. Wu and G. A. Sotzing, Conjugated polymers via electrochemical polymerization of thieno[3,4-b]thiophene (T34bT) and 3,4-ethylenedioxythiophene (EDOT), Langmuir, 19, 9479-9485 (2003).
29. V. Seshadri and G. A. Sotzing, Polymerization of two unsymmetrical isomeric monomers based on thieno[3,4-b]thiophene containing cyanovinylene spacers, Chem. Mater., 16, 5644-5649 (2004).
30. C. J. Neef, I. D. Brotherston and J. P. Ferraris, Synthesis and electronic properties of poly(2-phenylthieno[3,4-b]thiophene): A new low bandgap polymer, Chem. Mater., 11, 1957-1958 (1999).
31. M. Pomerantz, X. M. Gu and S. X. Zhang, Poly(2-decylthieno[3,4-b]thiophene-4,6-diyl). A new low bandgap conducting polymer, Macromolecules, 34, 1817-1822 (2001).
32. X. N. Zhang, M. Kohler and A. J. Matzger, Alkyl-substituted thieno[3,2-b]thiophene polymers and their dimeric subunits, Macromolecules, 37, 6306-6315 (2004).
33. S. B. Saidman, R. O. Garay and J. B. Bessone, Kinetic study of 3,6-dimethylthieno[3,2-b]thiophene electropoly-merization, J. Appl. Electrochem., 31, 839-844 (2001).
34. C. Taliani, R. Zamboni, R. Danieli, P. Ostoja, W. Porzio, R. Lazzaroni and J. L. Bredas, Influence of molecular architecture on electronic and transport-properties in sulfur-containing heterocyclic conducting polymers, Phys. Scr., 40, 781-785 (1989).
35. M. Turbiez, P. Frere, P. Leriche, N. Mercier and J. Roncali, Poly(3,6-dimethoxy-thieno[3,2-b]thiophene): a possible alternative to poly(3,4-ethylenedioxythiophene) (PEDOT), Chem. Commun., 1161-1163 (2005).
36. -1, J. Am. Chem. Soc., 128, 12604-12605 (2006).
37. T. Yamamoto and K. Takimiya, Facile synthesis of highly pi-extended heteroarenes, dinaphtho[2,3-b:2',3'-f ]chalcogenopheno[3,2-b]chalcogenophenes and their application to field-effect transistors, J. Am. Chem. Soc., 129, 2224-2225 (2007).
38. Y. N. Li, Y. L. Wu, P. Liu, M. Birau, H. L. Pan and B. S. Ong, Poly(2,5-bis(2-thienyl)-3,6-dialkylthieno[3,2-b]thiophene)s-high-mobility semiconductors for thin-film transistors, Adv. Mater., 18, 3029-3032 (2006).
39. I. McCulloch, M. Heeney, C. Bailey, K. Genevicius, I. Macdonald, M. Shkunov, D. Sparrowe, S. Tierney, R. Wagner, W. M. Zhang, M. L. Chabinyc, R. J. Kline, M. D. McGehee and M. F. Toney, Liquid-crystalline semiconducting polymers with high charge-carrier mobility, Nat. Mater., 5, 328-333 (2006).
40. D. M. DeLongchamp, R. J. Kline, E. K. Lin, D. A. Fischer, L. J. Richter, L. A. Lucas, M. Heeney, I. McCulloch and J. E. Northrup, High carrier mobility polythiophene thin films: structure determination by experiment and theory, Adv. Mater., 19, 833-837 (2007).
41. M. L. Chabinyc, M. F. Toney, R. J. Kline, I. McCulloch and M. Heeney, X-ray scattering study of thin films of poly(2,5-bis(3-alkylthiophen-2-yl)thieno[3,2-b]thiophene), J. Am. Chem. Soc., 129, 3226-3237 (2007).
42. E. Lim, B. J. Jung and H. K. Shim, Synthesis and characterization of a new light-emitting fluorene-thieno[3,2-b]thiophene-based conjugated copolymer, Macromolecules, 36, 4288-4293 (2003).
43. M. Heeney, C. Bailey, K. Genevicius, M. Shkunov, D. Sparrowe, S. Tierney and I. McCulloch, Stable polythiophene semiconductors incorporating thieno[2,3-b]thiophene, J. Am. Chem. Soc., 127, 1078-1079 (2005).
44. M. Shkunov, R. Simms, M. Heeney, S. Tierney and I. McCulloch, Ambipolar field-effect transistors based on solution-processable blends of thieno[2,3-b]thiophene terthiophene polymer and methanofullerenes, Adv. Mater., 17, 2608-2612 (2005).
45. T. Ozturk, E. Ertas and O. Mert, Dithienothiophenes, Tetrahedron, 61, 11055-11077 (2005).
46. M. Fujitsuka, T. Sato, H. Segawa and T. Shimidzu, Photochemical polymerization of oligothiophene and dithienothiophene, Synth. Met., 69, 309-310 (1995).
47. M. Fujitsuka, T. Sato, A. Watanabe, O. Ito and T. Shimidzu, Photochemical polymerization of dithienothiophenes, Chem. Lett., 285-286 (1996).
48. M. Biserni, A. Marinangeli and M. Mastragostino, Doped polydithienothiophene-a new cathode-active material, J. Electrochem. Soc., 132, 1597-1601 (1985).
49. P. Di Marco, M. Mastragostino and C. Taliani, Optical, electrical and electrochemical characterization of the doped polydithienothiophene, Mol. Cryst. Liq. Cryst, 118, 241-244 (1985).
50. C. Arbizzani, M. Catellani, M. Mastragostino and M. G. Cerroni, A spectroelectrochemical study of poly(dithienothiophenes), J. Electroanal. Chem., 423, 23-28 (1997).
51. C. Quattrocchi, R. Lazzaroni, J. L. Bredas, R. Zamboni and C. Taliani, Theoretical investigation of the structure and electronic properties of poly(dithieno[3,4-b/3',4'-d]thiophene), a small-band-gap conjugated polymer, Macromolecules, 26, 1260-1264 (1993).
52. S. Inaoka and D. M. Collard, Synthesis, polymerization and characterization of substituted dithieno[3,4-b:3',4'-d]thiophenes, J. Mater. Chem., 9, 1719-1725 (1999).
53. A. Cravino, H. Neugebauer, S. Luzzati, M. Catellani, A. Petr, L. Dunsch and N. S. Sariciftci, Positive and negative charge carriers in doped or photoexcited polydithienothiophenes: a comparative study using Raman, infrared and electron spin resonance spectroscopy, J. Phys. Chem. B, 106, 3583-3591 (2002).
54. A. Cravino, H. Neugebauer, S. Luzzati, M. Catellani and N. S. Sariciftci, Vibrational spectroscopy on pDTT3-A low bandgap polymer based on dithienothiophene, J. Phys. Chem. B, 105, 46-52 (2001).
55. H. Neugebauer, A. Cravino, S. Luzzati, M. Catellani, A. Petr, L. Dunsch and N. S. Sariciftci, Spectral signatures of positive and negative charged states in doped and photoexcited low band-gap polydithienothiophenes, Synth. Met., 139, 747-750 (2003).
56. J. Frey, A. D. Bond and A. B. Holmes, Improved synthesis of dithieno[3,2-b:2'3'-d]thiophene (DTT) and derivatives for cross coupling, Chem. Commun., 2424-2425 (2002).
57. J. Frey, S. Proemmel, M. A. Armitage and A. B. Holmes, Synthesis of dithieno[3,2-b;2'3'-d]thiophene, Org. Synth., 83, 209-216 (2006).
58. H. Sirringhaus, R. H. Friend, X. C. Li, S. C. Moratti, A. B. Holmes and N. Feeder, Bis(dithienothiophene) organic field-effect transistors with a high ON/OFF ratio, Appl. Phys. Lett., 71, 3871-3873 (1997).
59. X. C. Li, H. Sirringhaus, F. Garnier, A. B. Holmes, S. C. Moratti, N. Feeder, W. Clegg, S. J. Teat and R. H. Friend, A highly pi-stacked organic semiconductor for thin film transistors based on fused thiophenes, J. Am. Chem. Soc., 120, 2206-2207 (1998).
60. F. Garnier, A. Yassar, R. Hajlaoui, G. Horowitz, F. Deloffre, B. Servet, S. Ries and P. Alnot, Molecular engineering of organic semiconductors-design of self-assembly properties in conjugated thiophene oligomers, J. Am. Chem. Soc., 115, 8716-8721 (1993).
61. J. J. Morrison, M. M. Murray, X. C. Li, A. B. Holmes, S. C. Morratti, R. H. Friend and H. Sirringhaus, Preparation of bis(dithienothiophene) derivatives for organic thin film transistors, Synth. Met., 102, 987-988 (1999).
62. L. San Miguel, W. W. Porter and A. J. Matzger, Planar beta-linked oligothiophenes based on thieno[3,2-b]thiophene and dithieno[3,2-b:2'3'-d]thiophene fused units, Org. Lett., 9, 1005-1008 (2007).
63. Y. M. Sun, Y. W. Ma, Y. Q. Liu, Y. Y. Lin, Z. Y. Wang, Y. Wang, C. G. Di, K. Xiao, X. M. Chen, W. F. Qiu, B. Zhang, G. Yu, W. P. Hu and D. B. Zhu, High-performance and stable organic thin-film transistors based on fused thiophenes, Adv. Funct. Mater., 16, 426-432 (2006).
64. M. D. Iosip, S. Destri, M. Pasini, W. Porzio, K. P. Pernstich and B. Batlogg, New dithieno[3,2-b:2',3'-d]thiophene oligomers as promising materials for organic field-effect transistor applications, Synth. Met., 146, 251-257 (2004).
65. W. Porzio, S. Destri, M. Pasini, A. Bolognesi, A. Angiulli, P. Di Gianvincenzo, D. Natali, M. Sampietro, M. Caironi and L. Fumagalli, Oligo-and polymeric FET devices: thiophene-based active materials and their interaction with different gate dielectrics, Mater. Sci. Eng, C26, 996-1001 (2006).
66. P. Leriche, J. M. Raimundo, M. Turbiez, V. Monroche, M. Allain, F. X. Sauvage, J. Roncali, P. Frere and P. J. Skabara, Linearly extended tetrathiafulvalene analogues with fused thiophene units as pi-conjugated spacers, J. Mater. Chem., 13, 1324-1332 (2003).
67. R. P. Ortiz, M. C. R. Delgado, J. Casado, V. Hernandez, O. K. Kim, H. Y. Woo and J. T. L. Navarrete, Electronic modulation of dithienothiophene (DTT) as pi-center of D-pi-D chromophores on optical and redox properties: analysis by UV-vis-NIR and Raman spectroscopies combined with electrochemistry and quantum chemical DFT calculations, J. Am. Chem. Soc., 126, 13363-13376 (2004).
68. O. K. Kim and J. M. Lehn, Solvatochromism of non-linear optical chromophores containing the dithienothiophene group in donor-acceptor molecules, Chem. Phys. Lett., 255, 147-150 (1996).
69. O. K. Kim, K. S. Lee, H. Y. Woo, K. S. Kim, G. S. He, J. Swiatkiewicz and P. N. Prasad, New class of two-photon-absorbing chromophores based on dithienothiophene, Chem. Mater., 12, 284-286 (2000).
70. O. K. Kim, K. S. Lee, Z. Huang, W. B. Heuer and C. S. Paik-Sung, Oligothiophene as photonic/electronic property modulator, Opt. Mater., 21, 559-564 (2002).
71. O. K. Kim, H. Y. Woo, J. K. Kim, W. B. Heuer, K. S. Lee and C. Y. Kim, Bipolar behavior revealed by D-π-D chromophores bearing dithienothiophene (DTT) as π-center in redox and LE properties, Chem. Phys. Lett., 364, 432-437 (2002).
72. O. K. Kim, A. Fort, M. Barzoukas, M. Blanchard-Desce and J. M. Lehn, Nonlinear optical chromophores containing dithienothiophene as a new type of electron relay, J. Mater. Chem., 9, 2227-2232 (1999).
73. J. Casado, V. Hernandez, O. K. Kim, J. M. Lehn, J. T. L. Navarrete, S. D. Ledesma, R. P. Ortiz, M. C. R. Delgado, Y. Vida and E. Perez-Inestrosa, Vibrational and quantum-chemical study of nonlinear optical chromophores containing dithienothiophene as the electron relay, Chem. Eur. J., 10, 3805-3816 (2004).
74. G. Barbarella, L. Favaretto, M. Zambianchi, O. Pudova, C. Arbizzani, A. Bongini and M. Mastragostino, From easily oxidized to easily reduced thiophene-based materials, Adv. Mater., 10, 551-554 (1998).
75. 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).
76. L. Antolini, E. Tedesco, G. Barbarella, L. Favaretto, G. Sotgiu, M. Zambianchi, D. Casarini, G. Gigli and R. Cingolani, Molecular packing and photoluminescence efficiency in odd-membered oligothiophene 5,5-dioxides, J. Am. Chem. Soc., 122, 9006-9013 (2000).
77. G. Barbarella, L. Favaretto, G. Sotgiu, L. Antolini, G. Gigli, R. Cingolani and A. Bongini, Rigid-core oligothiophene-5,5-dioxides with high photoluminescence efficiencies both in solution and in the solid state, Chem. Mater., 13, 4112-4122 (2001).
78. E. Tedesco, F. Della Sala, L. Favaretto, G. Barbarella, D. Albesa-Jove, D. Pisignano, G. Gigli, R. Cingolani and K. D. M. Harris, Solid-state supramolecular organization, established directly from powder diffraction data and photoluminescence efficiency of rigid-core oligothiophene-S, S-dioxides, J. Am. Chem. Soc., 125, 12277-12283 (2003).
79. G. Sotgiu, M. Zambianchi, G. Barbarella, F. Aruffo, F. Cipriani and A. Ventola, Rigid-core fluorescent oligothiophene-5,5-dioxide isothiocyanates. Synthesis, optical characterization and conjugation to monoclonal antibodies, J. Org. Chem., 68, 1512-1520 (2003).
80. G. Sotgiu and G. Barbarella, Synthesis of photostable amine-reactive fluorescent dyes by postsynthetic conversion of bromide dithienothiophene derivatives, J. Org. Chem., 72, 4925-4931 (2007).
81. M. Catellani, B. Boselli, S. Luzzati and C. Tripodi, Dithienothiophene and dithienothiophene-5,5-dioxide copolymers for photovoltaics, Thin Solid Films, 403, 66-70 (2002).
82. 2, Thin Solid Films, 403, 52-56 (2002).
83. X. Zhan, Z. Tan, B. Domercq, Z. An, X. Zhang, S. Barlow, Y. Li, D. Zhu, B. Kippelen and S. R. Marder, A high-mobility electron-transport polymer with broad absorption and its use in field-effect transistors and all-polymer solar cells, J. Am. Chem. Soc., 129, 7246-7247 (2007).
84. T. Baumgartner, Pi-conjugated heterocyclic fused bithiophene materials, J. Inorg. Organomet. Polym. Mater., 15, 389-409 (2005).
85. P. Coppo and M. L. Turner, Cyclopentadithiophene based electroactive materials, J.Mater. Chem., 15, 1123-1133 (2005).
86. G. Koeckelberghs, L. DeCremer, A. Persoons and T. Verbiest, Influence of the substituent and polymerization methodology on the properties of chiral poly(dithieno[3,2-b:2',3'-d]pyrrole)s, Macromolecules, 40, 4173-4181 (2007).
87. K. Ogawa and S. C. Rasmussen, N-functionalized poly(dithieno[3,2-b:2',3'-d]pyrrole)s: highly fluorescent materials with reduced bandgaps, Macromolecules, 39, 1771-1778 (2006).
88. T. Baumgartner and W. Wilk, Synthesis and unexpected reactivity of Si-H functionalized dithieno[3,2-b:2',3'-d]phospholes, Org. Lett., 8, 503-506 (2006).
89. T. Neumann, Y. Dienes and T. Baumgartner, Highly sensitive sensory materials for fluoride ions based on the dithieno[3,2-b:2',3'-d]phosphole system, Org. Lett., 8, 495-497 (2006).
90. S. Durben, Y. Dienes and T. Baumgartner, Cationic dithieno[3,2-b:2',3'-d]phospholes: a new building block for luminescent, conjugated polyelectrolytes, Org. Lett., 8, 5893-5896 (2006).
91. G. Klaerner and R. D. Miller, Polyfluorene derivatives: effective conjugation lengths from well-defined oligomers, Macromolecules, 31, 2007-2009 (1998).
92. B. Liu, W. L. Yu, Y. H. Lai and W. Huang, Synthesis, characterization and structure-property relationship of novel fluorene-thiophene-based conjugated copolymers, Macromolecules, 33, 8945-8952 (2000).
93. M. S. Liu, J. D. Luo and A. K. Y. Jen, Efficient green-light-emitting diodes from silole-containing copolymers, Chem. Mater., 15, 3496-3500 (2003).
94. K. Mouri, A. Wakamiya, H. Yamada, T. Kajiwara and S. Yamaguchi, Ladder distyrylbenzenes with silicon and chalcogen bridges: synthesis, structures and properties, Org. Lett., 9, 93-96 (2007).
95. K. Takimiya, Y. Konda, H. Ebata, N. Niihara and T. Otsubo, Facile synthesis, structure and properties of benzo[1,2-b:4,5-b']dichalcogenophenes, J. Org. Chem., 70, 10569-10571 (2005).
96. K. Takimiya, Y. Kunugi, Y. Konda, N. Niihara and T. Otsubo, 2,6-Diphenylbenzo[1,2-b:4,5-b']dichalcogenophenes: a new class of high-performance semiconductors for organic field-effect transistors, J. Am. Chem. Soc., 126, 5084-5085 (2004).
97. C. H. Wang, R. R. Hu, S. Liang, J. H. Chen, Z. Yang and J. Pei, Linear C-2-symmetric polycyclic benzodithio-phene: efficient, highly diversified approaches and the optical properties, Tetrahedron Lett., 46, 8153-8157 (2005).
98. H. L. Pan, Y. N. Li, Y. L. Wu, P. Liu, B. S. Ong, S. P. Zhu and G. Xu, Low-temperature, solution-processed, high-mobility polymer semiconductors for thin-film transistors, J. Am. Chem. Soc., 129, 4112-4113 (2007).
99. B. Wex, B. R. Kaafarani and D. C. Neckers, Efficient isomer-pure synthesis of a benzo[b]thiophene analogue of pentacene, J. Org. Chem., 69, 2197-2199 (2004).
100. B. Wex, B. R. Kaafarani, K. Kirschbaum and D. C. Neckers, Synthesis of the anti and syn isomers of thieno[ff']bis[1]benzothiophene. Comparison of the optical and electrochemical properties of the anti and syn isomers, J. Org. Chem., 70, 4502-4505 (2005).
101. B. Wex, B. R. Kaafarani, E. O. Danilov and D. C. Neckers, Altering the emission behavior with the turn of a thiophene ring: the photophysics of condensed ring systems of alternating benzenes and thiophenes, J. Phys. Chem. A, 110, 13754-13758 (2006).
102. K. Takimiya, K. Kato, Y. Aso, F. Ogura and T. Otsubo, Synthesis, structures and properties of two isomeric naph-thodithiophenes and their methyl, methylthio and 2-thienyl derivatives; application to conductive charge-transfer complexes and low-bandgap polymers, Bull. Chem. Soc. Jpn., 75, 1795-1805 (2002).
103. Y. Kunugi, K. Takimiya, K. Yamashita, Y. Aso and T. Otsubo, Organic field-effect transistors using di(2-thienyl)naphthodithiophenes as active layers, Chem. Lett., 958-959 (2002).
104. K. Takimiya, Y. Kunugi, Y. Toyoshima and T. Otsubo, 2,6-diarylnaphtho[1,8-fcc:5,4-b'c']dithiophenes as new high-performance semiconductors for organic field-effect transistors, J. Am. Chem. Soc., 127, 3605-3612 (2005).
105. G. Zotti, S. Zecchin, G. Schiavon, B. Vercelli, A. Berlin and W. Porzio, Electrostatically self-assembled multilayers of novel symmetrical rigid-rod polyanionic and polycationic polythiophenes on ITO/glass and gold electrodes, Chem. Mater., 16, 2091-2100 (2004).
106. M. Zhang, H. N. Tsao, W. Pisula, C. D. Yang, A. K. Mishra and K. Müllen, Field-effect transistors based on a benzothiadiazole-cyclopentadithiophene copolymer, J. Am. Chem. Soc., 129, 3472-3473 (2007).
107. Z. Zhu, D. Waller, R. Gaudiana, M. Morana, D. Muhlbacher, M. Scharber and C. Brabec, Panchromatic conjugated polymers containing alternating donor/acceptor units for photovoltaic applications, Macromolecules, 40, 1981-1986 (2007).
108. D. Muhlbacher, M. Scharber, M. Morana, Z. G. Zhu, D. Waller, R. Gaudiana and C. Brabec, High photovoltaic performance of a low-bandgap polymer, Adv. Mater., 18, 2884-2889 (2006).
109. Y. Ie, M. Nitani, M. Ishikawa, K.-i. Nakayama, H. Tada, T. Kaneda and Y. Aso, Electronegative oligothiophenes for n-type semiconductors: difluoromethylene-bridged bithiophene and its oligomers, Org. Lett., 9, 2115-2118 (2007).
110. Y. Mazaki and K. Kobayashi, Synthesis of tetrathieno-acene and pentathieno-acene-UV-spectral trend in a homologous series of thieno-acenes, Tetrahedron Lett., 30, 3315-3318 (1989).
111. X. N. Zhang and A. J. Matzger, Effect of ring fusion on the electronic absorption and emission properties of oligothiophenes, J. Org. Chem., 68, 9813-9815 (2003).
112. N. Sato, Y. Mazaki, K. Kobayashi and T. Kobayashi, Linearly condensed/polythiophenes-characteristic molecular aggregation of thieno[2",3"-4',5']thieno[2',3'-d]thieno[3,2-b]thiophene crystals revealed by ultraviolet pho-toelectron spectroscopy, J. Chem. Soc., Perkin Trans. 2, 765-770 (1992).
113. Y. Mazaki and K. Kobayashi, Crystal and molecular-structure of thieno[2",3"/4',5']thieno[2',3'-d]thieno[3,2-b]thiophene as a hydrogen-poor heterocycle, J. Chem. Soc., Perkin Trans. 2, 761-764 (1992).
114. K. Xiao, Y. Q. Liu, T. Qi, W. Zhang, F. Wang, J. H. Gao, W. F. Qiu, Y. Q. Ma, G. L. Cui, S. Y. Chen, X. W. Zhan, G. Yu, J. G. Qin, W. P. Hu and D. B. Zhu, A highly pi-stacked organic semiconductor for field-effect transistors based on linearly condensed pentathienoacene, J. Am. Chem. Soc., 127, 13281-13286 (2005).
115. X. N. Zhang, A. P. Cote and A. J. Matzger, Synthesis and structure of fused alpha-oligothiophenes with up to seven rings, J. Am. Chem. Soc., 127, 10502-10503 (2005).
116. M. Q. He and F. X. Zhang, Synthesis and structure of alkyl-substituted fused thiophenes containing up to seven rings, J. Org. Chem., 72, 442-451 (2007).
117. R. M. Osuna, X. N. Zhang, A. J. Matzger, V. Hernandez and J. T. L. Navarrete, Combined quantum chemical density functional theory and spectroscopic Raman and UV-vis-NIR study of oligothienoacenes with five and seven rings, J. Phys. Chem. A, 110, 5058-5065 (2006).
118. W. Schroth, E. Hintzsche, H. Jordan, T. Jende, R. Spitzner and I. Thondorf, 1,2-Dithiins and precursors. 17. Synthesis and properties of thieno annellated 1,2-dithiins-structural influence on color, Tetrahedron, 53, 7509-7528 (1997).
119. W. Schroth, E. Hintzsche, M. Felicetti, R. Spitzner, J. Sieler and R. Kempe, Concerning the questionable existence of thioxoindigoid compounds, Angew. Chem. Int. Ed. Engl., 33, 739-741 (1994).
120. W. Schroth, E. Hintzsche, H. Viola, R. Winkler, H. Klose, R. Boese, R. Kempe and J. Sieler, Bis(benzo[4, 5]thieno)[3,2-c-2',3'-e][1, 2]dithiine, a valence isomer of dithioxo-thioindigo, Chem. Ber., 127, 401-408 (1994).
121. T. Okamoto, K. Kudoh, A. Wakamiya and S. Yamaguchi, General synthesis of thiophene and selenophene-based heteroacenes, Org. Lett., 7, 5301-5304 (2005).
122. K. Kudoh, T. Okamoto and S. Yamaguchi, Reactions of fused polycyclic 1,2-dithiins with transition metals: synthesis of heteroacenes via desulfurization, Organometallics, 25, 2374-2377 (2006).
123. 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).
124. K. Oyaizu, T. Iwasaki, Y. Tsukahara and E. Tsuchida, Linear ladder-type pi-conjugated polymers composed of fused thiophene ring systems, Macromolecules, 37, 1257-1270 (2004).
125. R. M. Osuna, R. P. Ortiz, V. Hernandez, J. T. L. Navarrete, M. Miyasaka, S. Rajca, A. Rajca and R. Glaser, Helically annelated and cross-conjugated beta-oligothiophenes: a Fourier transform Raman spectroscopic and quantum chemical density functional theory study, J. Phys. Chem. C, 111, 4854-4860 (2007).
126. M. Miyasaka, A. Rajca, M. Pink and S. Rajca, Cross-conjugated oligothiophenes derived from the (C2S)(n) helix: asymmetric synthesis and structure of carbon-sulfur [11]helicene, J. Am. Chem. Soc., 127, 13806-13807 (2005).
127. M. Miyasaka, A. Rajca, M. Pink and S. Rajca, Chiral molecular glass: synthesis and characterization of enan-tiomerically pure thiophene-based [7]helicene, Chem. Eur. J., 10, 6531-6539 (2004).
128. A. Rajca, M. Miyasaka, M. Pink, H. Wang and S. Rajca, Helically annelated and cross-conjugated oligothiophenes: asymmetric synthesis, resolution and characterization of a carbon-sulfur [7]helicene, J. Am. Chem. Soc., 126, 15211-15222 (2004).
129. M. Miyasaka and A. Rajca, Synthesis of functionalized carbon-sulfur [5]helicene: Pd-catalyzed Negishi cross-coupling between the beta-positions of thiophenes, Synlett, 177-181 (2004).
130. T. B. Freedman, X. L. Cao, A. Rajca, H. Wang and L. A. Nafie, Determination of absolute configuration in molecules with chiral axes by vibrational circular dichroism: A C-2-symmetric annelated heptathiophene and a D-2-symmetric dimer of 1,1'-binaphthyl, J. Phys. Chem. A, 107, 7692-7696 (2003).
131. A. Rajca, H. Wang, M. Pink and S. Rajca, Annelated heptathiophene: a fragment of a carbon-sulfur helix, Angew. Chem. Int. Ed., 39, 4481-4483 (2000).
132. M. Miyasaka and A. Rajca, Synthesis of dithieno[2,3-b:3',2'-d]thiophenes-building blocks for cross-conjugated beta-oligothiophenes, J. Org. Chem., 71, 3264-3266 (2006).
133. V. G. Nenajdenko, V. V. Sumerin, K. Y. Chernichenko and E. S. Balenkova, A new route to annulated oligoth-iophenes, Org. Lett., 6, 3437-3439 (2004).
134. J. H. Dopper, D. Oudman and H. Wynberg, Use of thieno[2,3-b]thiophene in synthesis of heterohelicenes by double photocyclizations, J. Am. Chem. Soc., 95, 3692-3698 (1973).
135. J. H. Dopper and H. Wynberg, Heterocirculenes-new class of polycyclic aromatic-hydrocarbons, Tetrahedron Lett., 763-766 (1972).
136. U. Dahlmann and R. Neidlein, Rhodium(I)-mediated synthesis of benzo[2,1-b:3,4-b':5,6-c"]trithiophenes and naphtho[2,1-b:3,4-b']dithiophenes, Synthesis, 1027-1033 (1997).
137. J. Pei, W. Y. Zhang, J. Mao and X. H. Zhou, Helical polycyclic aromatics containing thiophenes: synthesis and properties, Tetrahedron Lett., 47, 1551-1554 (2006).
138. F. Wudl, R. C. Haddon, E. T. Zellers and F. B. Bramwell, 3,4:3',4'-Bibenzo[b]thiophene, J. Org. Chem., 44, 2491-2493 (1979).
139. Y. Kono, H. Miyamoto, Y. Aso, T. Otsubo, F. Ogura, T. Tanaka and M. Sawada, 3,3'-4,4'-Bis(thieno[2,3-b]thiophene)-a novel fused heteroarene, Angew. Chem. Int. Ed. Engl., 28, 1222-1224 (1989).
140. K. Imamura, K. Takimiya, Y. Aso and T. Otsubo, Triphenyleno[1,12-fccd: 4,5-b'c'd':8,9-b"c"d"]trithiophene: the first bowl-shaped heteroaromatic, Chem. Commun., 1859-1860 (1999).
141. 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).
142. K. Y. Chernichenko, V. V. Sumerin, R. V. Shpanchenko, E. S. Balenkova and V. G. Nenajdenko, 'Sulflower': a new form of carbon sulfide, Angew. Chem. Int. Ed., 45, 7367-7370 (2006).
143. 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).
144. 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).
145. B. A. Gregg, The photoconversion mechanism of excitonic solar cells, MRS Bull., 30, 20-22 (2005).
146. Z. K. Chen, W. Huang, L. H. Wang, E. T. Kang, B. J. Chen, C. S. Lee and S. T. Lee, A family of electroluminescent silyl-substituted poly(_p-phenylenevinylene)s: synthesis, characterization and structure-property relationships, Macromolecules, 33, 9015-9025 (2000).
147. S. Janietz, D. D. C. Bradley, M. Grell, C. Giebeler, M. Inbasekaran and E. P. Woo, Electrochemical determination of the ionization potential and electron affinity of poly(9,9-dioctylfluorene), Appl. Phys. Lett., 73, 2453-2455 (1998).