Theoretical Studies on Thiophene-Containing Compounds

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

Volumn , Issue , 2009, Pages 365-417

  Zade, Sanjio S ^a   Bendikov, Michael ^b  

^a INDIAN INSTITUTE OF SCIENCE EDUCATION AND RESEARCH KOLKATA   (India)

^b WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

FT IR and FT Raman spectroscopies and DFT quantum chemical calculations; HOMO LUMO gap and bandgap calculations; Organic light emitting diodes (OLEDs); Quantum chemical techniques and oligomers and polymers based on end capped oligofluorene thiophenes; Quinoid oligothiophenes; Thiophene containing compounds and advancing field of organic electronic materials; Twisting (inter ring deviation from planarity) in oligo and polythiophenes; UV Vis spectra

Indexed keywords

EID: 78751536515     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470745533.ch8     Document Type: Chapter

References (208)

1. K. Müllen, G. Wegner (eds), Electronic Materials: the Oligomer Approach, Wiley-VCH Verlag GmbH, Weinheim, 1998;
2. D. Fichou (ed.), Handbook ofOligo-and Polythiophenes, Wiley-VCH Verlag GmbH, Weinheim, 1999;
3. T. A. Skotheim, R. L. Elsenbaumer, J. R. Reynolds (eds), Handbook of Conducting Polymers, 2nd edn, Marcel Dekker, New York, 1998;
4. J. L. Bredas, R. Silbey (eds), Conjugated Polymers: the Novel Science and Technology of Highly Conducting and Nonlinear Optically Active Materials, Klüwer Academic, Dordrecht, 1991;
5. H. S. Nalwa (ed.), Handbook of Organic Conductive Molecules and Polymers, Vols 1-4, John Wiley &Sons, Inc., New York, 1997;
6. J. M. Tour, Conjugated macromolecules of precise length and constitution. Organic synthesis for the construction of nanoarchitectures, Chem. Rev., 96, 537-553 (1996);
7. J. Roncali, Synthetic principles for bandgap control in linear π-conjugated systems, Chem. Rev., 97, 173-206 (1997);
8. L. B. Groenendaal, F. Jonas, D. Freitag, H. Pielartzik, J. R. Reynolds, Poly(3,4-ethylenedioxythiophene) and its derivatives: past, present and future, Adv. Mater., 12, 481-494 (2000);
9. J. L. Bredas, D. Beljonne, V. Coropceanu, J. Cornil, Charge-transfer and energy-transfer processes in pi-conjugated oligomers and polymers: a molecular picture, Chem. Rev., 104, 4971-5004 (2004);
10. I. F. Perepichka, D. F. Perepichka, H. Meng, F. Wudl, Light-emitting polythiophenes, Adv. Mater., 17, 2281-2305 (2005).
11. J. Cornil, D. Beljonne, J. L. Bredas, A quantum chemical approach to conjugated oligomers: the case of oligothiophenes, in Electronic Materials: the Oligomer Approach, ed. K. Müllen, G. Wegner, Wiley-VCH Verlag GmbH, Weinheim, 1998, pp. 432-447.
12. J. Cornil, D. Beljonne, V. Parente, R. Lazzaroni, J. L. Bredas, Geometric and electronic structure and optical response of oligo-and polythiophenes: relation to their use in electro-optic and photonic devices, in Handbook ofOligo-and Polythiophenes, ed. D. Fichou, Wiley-VCH Verlag GmbH, Weinheim, 1999, pp. 317-360.
13. U. Salzner, Conjugated organic polymers: from bulk to molecular wire, in Handbook of Theoretical and Computational Nanotechnology, Vol. 8, ed. M. Rieth, W. Schommers, American Scientific Publishers, Stevenson Ranch, CA, 2006, pp. 203-251;
14. U. Salzner, Theoretical design of conjugated organic polymers, Curr. Org. Chem., 8, 569-590 (2004).
15. V. Coropceanu, J. Cornil, D. A. da Silva Filho, Y. Olivier, R. Silbey, J. L. Bredas, Charge transport in organic semiconductors, Chem. Rev., 107, 926-952 (2007);
16. C. R. Newman, C. D. Frisbie, D. A. da Silva Filho, J. L. Bredas, P. C. Ewbank, K. R. Mann, Introduction to organic thin film transistors and design of n-channel organic semiconductors, Chem. Mater., 16, 4436-4451 (2004);
17. J. Cornil, D. Beljonne, J.-P. Calbert, J. L. Bredas, Interchain interactions in organic π-conjugated materials: impact on electronic structure, optical response and charge transport, Adv. Mater., 13, 1053-1067 (2001);
18. J. L. Bredas, Electronic structure and optical properties of conducting and semiconducting conjugated oligomers and polymers: an overview of the quantum-mechanical approaches, Synth. Met., 84, 3-10 (1997);
19. J. L. Bredas, Conjugated polymers and oligomers. Designing novel materials using a quantum-chemical approach, Adv. Mater., 7, 263-274 (1995).
20. G. Horowitz, X. Peng, D. Fichou, F. Garnier, The oligothiophene-based field-effect transistor: how it works and how to improve it, J. Appl. Phys., 67, 528-532 (1990);
21. J. Paloheimo, P. Kmvalainen, H. Stubb, E. Vuorimaa, P. Yli-Lahti, Molecular field-effect transistors using conducting polymer Langmuir-Blodgett films, Appl. Phys. Lett., 56, 1157-1159 (1990);
22. F. Garnier, R. Hajlaoui, A. Yassar, P. Srivastava, All-polymer field-effect transistor realized by printing techniques, Science, 265, 1864-1866 (1994);
23. A. Dodabalapur, H. E. Katz, L. Torsi, R. C. Haddon, Organic heterostructure field-effect transistors, Science, 269, 1560-1562 (1995);
24. C. D. Dimitrakopoulos, P. R. L. Malenfant, Organic thin film transistors for large area electronics, Adv. Mater., 14, 99-117 (2002);
25. G. Horowitz, Organic field-effect transistors, Adv. Mater., 10, 365-377 (1998);
26. H. E. Katz, Organic molecular solids as thin film transistor semiconductors, J. Mater. Chem., 7, 369-376 (1997);
27. M. Halik, H. Klauk, U. Zschieschang, G. Schmid, S. Ponomarenko, S. Kirchmeyer, W. Weber. Relationship between molecular structure and electrical performance of oligothiophene organic thin film transistors. Adv. Mater., 15, 917-922 (2003).
28. N. Tessler, J. Veres, O. Globerman, N. Rappaport, Y. Preezant, Y. Roichman, O. Solomesch, S. Tal, E. Gershman, M. Adler, V. Zolotarev, V. Gorelik, Y. Eichen, Conjugated polymer electronics-engineering materials and devices, in Handbook of Conducting Polymers. Conjugated Polymers: Processing and Applications, 3rd edn, ed. T. A. Skotheim, J. R. Reynolds, CRC Press, Boca Raton, FL, 2007, Chapter 7, pp. 7-1-7-42.
29. F. Geiger, M. Stoldt, H. Schweizer, P. Bauerle, E. Umbach, Electroluminescence from oligothiophene-based light-emitting devices, Adv. Mater., 5, 922-925 (1993);
30. U. Mitschke, P. Bauerle, The electroluminescence of organic materials, J. Mater. Chem., 10, 1471-1507 (2000);
31. G. Barbarella, L. Favaretto, G. Sotgiu, M. Zambianchi, A. Bongini, C. Arbizzani, M. Mastragostino, M. Anni, G. Gigli, R. Cingolani, Tuning solid-state photoluminescence frequencies and efficiencies of oligomers containing one central thiophene-5,5-dioxide unit, J. Am. Chem. Soc., 122, 11971-11978 (2000);
32. G. Barbarella, L. Favaretto, G. Sotgiu, L. Antolini, G. Gigli, R. Cingolani, 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).
33. N. D. Robinson, M. Berggren, Printing organic electronics on flexible substrates, in Handbook of Conducting Polymers. Conjugated Polymers: Processing and Applications, 3rd edn, ed. T. A. Skotheim, J. R. Reynolds, CRC Press, Boca Raton, FL, 2007, Chapter 4, pp. 4-1-4-26.
34. C. J. Brabec, N. S. Sariciftci, J. C. Hummelen, Plastic solar cells, Adv. Funct. Mater., 11, 15-26 (2001);
35. H. Hoppe, N. S. Sariciftci, Organic solar cells: an overview, J. Mater. Res., 19, 1924-1945 (2004).
36. A. J. Mozer, N. S. Sariciftci, Conjugated polymer-based photovoltaic devices, in Handbook of Conducting Polymers. Conjugated Polymers: Processing and Applications, 3rd edn, ed. T. A. Skotheim, J. R. Reynolds, CRC Press, Boca Raton, FL, 2007, Chapter 10, pp. 10-1-10-37.
37. A. L. Dyer, J. R. Reynolds, Electrochromism of conjugated conducting polymers, in Handbook of Conducting Polymers. Conjugated Polymers: Theory, Synthesis, Properties and Characterization, 3rd edn, ed. T. A. Skotheim, J. R. Reynolds, CRC Press, Boca Raton, FL, 2007, Chapter 20, pp. 20-1-20-63.
38. S. Yang, P. Olishevski, M. Kertesz, Bandgap calculations for conjugated polymers, Synth. Met., 141, 171-177 (2004);
39. M. Kertesz, C. H. Choi, S. Yang, Conjugated polymers and aromaticity, Chem. Rev., 105, 3448-3481 (2005).
40. J. Gierschner, J. Cornil, H. J. Egelhaaf, Optical bandgaps of π-conjugated organic materials at the polymer limit: experiment and theory, Adv. Mater., 19, 173-191 (2007).
41. C. Aleman, J. Casanovas, Comparative theoretical study of heterocyclic conducting oligomers: neutral and oxidized forms, J. Phys. Chem. C, 111, 4823-4830 (2007) and references therein.
42. M. A. De Oliveira, H. A. Duarte, J.-M. Pernaut, W. B. De Almeida, Energy gaps of α,α'-substituted oligothiophenes from semiempirical, ab initio and density functional methods, J. Phys. Chem. A, 104, 8256-8262 (2000).
43. U. Salzner, P. G. Pickup, R. A. Poirier, J. B. Lagowski, Accurate method for obtaining bandgaps in conducting polymers using a DFT/hybrid approach, J. Phys. Chem. A, 102, 2572-2578 (1998).
44. S. S. Zade, M. Bendikov, From oligomers to polymer: convergence in the HOMO-LUMO gaps of conjugated oligomers, Org. Lett., 8, 5243-5246 (2006).
45. T. C. Chung, J. Kaufman, A. J. Heeger, F. Wudl, Charge storage in doped poly(thiophene): optical and electrochemical studies, Phys. Rev. B, 30, 702-710 (1984).
46. M. Kobayashi, J. Chen, T. C. Chung, F. Moraes, A. J. Heeger, F. Wudl, Synthesis and properties of chemically coupled poly(thiophene), Synth. Met., 9, 77-86 (1984).
47. T.-T. Ong, S.-C. Ng, H. S. O. Chan, Synthesis, characterization and electrochemical properties of polybise-lenophene, Polymer, 44, 5597-5603 (2003).
48. D. Chakraborty, J. B. Lagowski, Configuration interaction study of singlet excited state of thiophene and its cyano derivative oligomers, J. Chem. Phys., 115, 184-194 (2001).
49. D. Beljonne, J. Cornil, R. H. Friend, R. A. J. Janssen, J. L. Bredas, Influence of chain length and derivatization on the lowest singlet and triplet states and intersystem crossing in oligothiophenes, J. Am. Chem. Soc., 118, 6453-6461 (1996).
50. H. Chosrovian, S. Rentsch, D. Grebner, D. U. Dahm, E. Birckner, Time-resolved fluorescence studies on thiophene oligomers in solution, Synth. Met., 60, 23-26 (1993);
51. R. A. J. Janssen, D. Moses, N. S. Sariciftci, Electron and energy transfer processes of photoexcited oligothiophenes onto tetracyanoethylene and C60, J. Chem. Phys., 101, 9519-9527 (1994);
52. R. A. J. Janssen, L. Smilowitz, N. S. Sariciftci, D. Moses, Triplet-state photoexcitations of oligothiophene films and solutions, J. Chem. Phys., 101, 1787-1798 (1994).
53. T. A. Chen, R. D. Rieke, Polyalkylthiophenes with the smallest bandgap and the highest intrinsic conductivity, Synth. Met., 60, 175-177 (1993);
54. R. D. McCullough, R. D. Lowe, M. Jayaraman, D. L. Anderson, Design, synthesis and control of conducting polymer architectures: structurally homogeneous poly(3-alkylthiophenes), J. Org. Chem., 58, 904-912 (1993).
55. J. Gama Amazonas, J. R. Gmmaraes, S. Cristina Santos Costa, B. Laks, J. Del Nero, Theoretical modelling of low bandgap organic oligomers, THEOCHEM, 759, 87-91 (2006).
56. U. Salzner, Does the donor-acceptor concept work for designing synthetic metals? 1. Theoretical investigation of poly(3-cyano-3'-hydroxybithiophene), J. Phys. Chem. B, 106, 9214-9220 (2002).
57. U. Salzner, M. E. Kose, Does the donor-acceptor concept work for designing synthetic metals? 2. Theoretical investigation of copolymers of 4-(dicyanomethylene)-4_ff-cyclopenta[2,1-b:3,4-b']dithiophene and 3,4-(ethylenedioxy)thiophene, J. Phys. Chem. B, 106, 9221-9226 (2002).
58. U. Salzner, O. Karalti, S. Durdagi, Does the donor-acceptor concept work for designing synthetic metals? 3. Theoretical investigation of copolymers between quinoid acceptors and aromatic donors, J. Mol. Model, 12, 687-701 (2006).
59. C. Aleman, E. Armelin, J. I. Iribarren, F. Liesa, M. Laso, J. Casanovas, Structural and electronic properties of 3,4-ethylenedioxythiophene, 3,4-ethylenedisulfanylfurane and thiophene oligomers: a theoretical investigation, Synth. Met., 149, 151-156 (2005).
60. A. O. Patil, A. J. Heeger, F. Wudl, Optical properties of conducting polymers, Chem. Rev., 88, 183-200, (1988);
61. A. J. Heeger, S. Kivelson, J. R. Schrieffer, W. P. Su, Solitons in conducting polymers, Rev. Mod. Phys., 60, 781-850 (1988);
62. J. L. Bredas, G. B. Street, Polarons, bipolarons and solitons in conducting polymers, Acc. Chem. Res., 18, 309-315 (1985);
63. L. L. Miller, K. R. Mann, π-Dimers and π-stacks in solution and in conducting polymers, Acc. Chem. Res., 29, 417-423 (1996);
64. W. R. Salaneck, R. H. Friend, J. L. Bredas, Electronic structure of conjugated polymers: consequences of electron-lattice coupling, Phys. Rep., 319, 231-251 (1999);
65. Y. Furukawa, Electronic absorption and vibrational spectroscopies of conjugated conducting polymers, J. Phys. Chem., 100, 15644-15653 (1996).
66. K. Kaneto, S. Hayashi, S. Ura, K. Yoshino, ESR and transport studies in electrochemically doped polythio-phene film, J. Phys. Soc. Jpn., 54, 1146-1153 (1984);
67. J. Chen, A. J. Heeger, F. Wudl, Confined soliton pairs (bipolarons) in polythiophene: in-situ magnetic resonance measurements, Solid State Commun., 58, 251-257 (1986);
68. N. Colaneri, M. Nowak, D. Spiegel, S. Hotta, A. J. Heeger, Bipolarons in poly(3-methylthiophene): spectroscopic, magnetic and electrochemical measurements, Phys. Rev. B, 36, 7964-7968 (1987);
69. D. Fichou, G. Horowitz, B. Xu, F. Garnier, Stoichiometric control of the successive generation of the radical cation and dication of extended a-conjugated oligothiophenes: a quantitative model for doped polythiophene, Synth. Met., 39, 243-259 (1990).
70. J. L. Bredas, B. Themans, J. G. Fripiat, J. M. Andre, R. R. Chance, Highly conducting polyparaphenylene, polypyrrole and polythiophene chains: an ab initio study of the geometry and electronic-structure modifications upon doping, Phys. Rev. B, 29, 6761-6773 (1984);
71. J. L. Bredas, F. Wudl, A. J. Heeger, Polarons and bipolarons in doped polythiophene: a theoretical investigation, Solid State Commun., 63, 577-580 (1987);
72. D. Bertho, C. Jouanin, Polaron and bipolaron excitations in doped polythiophene, Phys. Rev. B, 35, 626-633 (1987);
73. G. M. e Silva, Electric-field effects on the competition between polarons and bipolarons in conjugated polymers, Phys. Rev. B, 61, 10777-10781 (2000).
74. A. J. W. Tol, The instability of a bipolaron versus two polarons: charge localization in cyclododecathiophene, Synth. Met., 74, 95-98 (1995);
75. A. J. W. Tol, The electronic and geometric structure of dications of oligo-thiophenes, Chem. Phys., 208, 73-79 (1996).
76. C. Ehrendorfer, A. Karpfen, Spatial extension of a bipolaronic defect in oligothiophenes and in polythiophene: a combined semiempirical and ab initio study, J. Phys. Chem., 98, 7492-7496 (1994);
77. E. Yurtsever, Multiple bipolaron formation in oligothiophenes, Synth. Met., 105, 179-183 (1999).
78. G. Brocks, Polarons and bipolarons in oligothiophenes: a first principles study, Synth. Met., 102, 914-915 (1999).
79. M. G. Hill, K. R. Mann, L. L. Miller, J.-F. Penneau, Oligothiophene cation radical dimers. An alternative to bipolarons in oxidized polythiophene, J. Am. Chem. Soc., 114, 2728-2730 (1992);
80. M. G. Hill, J.-F. Penneau, B. Zinger, K. R. Mann, L. L. Miller, Oligothiophene cation radicals. π-Dimers as alternatives to bipolarons in oxidized polythiophenes, Chem. Mater., 4, 1106-1113 (1992);
81. D. Beljonne, J. Cornil, H. Sirringhaus, P. J. Brown, M. Shkunov, R. H. Friend, J. L. Bredas, Optical signature of delocalized polarons in conjugated polymers, Adv. Funct. Mater., 11, 229-234 (2001);
82. G. Brocks, π-Dimers of oligothiophene cations, J. Chem. Phys., 112, 5353-5363 (2000).
83. M. C. dos Santos, M. Pickholz, The electronic structure of oligothiophenes, J. Non-Cryst. Solids, 338-340, 586-589 (2004).
84. D. A. Scherlis, N. Marzari, π-Stacking in charged thiophene oligomers, J. Phys. Chem. B, 108, 17791-17795 (2004).
85. Y. Gao, C.-G. Liu, Y.-S. Jiang, Electronic structure of thiophene oligomer dications: an alternative interpretation from the spin-unrestricted DFT study, J. Phys. Chem. A, 106, 5380-5384 (2002).
86. V. M. Geskin, J. L. Bredas, Polaron pair versus bipolaron on oligothiophene chains: a theoretical study of the singlet and triplet states, ChemPhysChem, 4, 498-505 (2003).
87. S. S. Zade, M. Bendikov, Theoretical study of long oligothiophene dications: bipolaron vs polaron pair vs triplet state, J. Phys. Chem. B, 110, 15839-15846 (2006).
88. S. S. Zade, M. Bendikov, Theoretical study of long oligothiophene polycations as a model for doped polythiophene, J. Phys. Chem. C, 111, 10662-10672 (2007).
89. H. Nakanishi, N. Sumi, Y. Aso, T. Otsubo, Synthesis and properties of the longest oligothiophenes: the icosamer and heptacosamer, J. Org. Chem., 63, 8632-8633 (1998);
90. N. Sumi, H. Nakanishi, S. Ueno, K. Takimiya, Y. Aso, T. Otsubo, Synthesis and properties of a series of the longest oligothiophenes up to the 48-mer, Bull. Chem. Soc. Jpn., 74, 979-988 (2001).
91. F. Demanze, J. Cornil, F. Garnier, G. Horowitz, P. Valat, A. Yassar, R. Lazzaroni, J. L. Bredas, Tuning of the electronic and optical properties of oligothiophenes via cyano substitution: a joint experimental and theoretical study, J. Phys. Chem. B, 101, 4553-4558 (1997).
92. F. Demanze, P. Godillot, F. Garnier, P. Hapiot, Electrochemical oxidative coupling of cyano-substituted oligoth-iophenes, J. Electroanal. Chem., 414, 61-67 (1996).
93. D. Beljonne, F. Meyers, J. L. Bredas, Excited states in bis-substituted polyenes: configuration interaction description of the vertical excitation energies and nonlinear optical properties, Synth. Met., 80, 211-222 (1996).
94. L. Yang, J. K. Feng, A.-M. Ren, Structural, electronic and optical properties of a series of oligofluorene-thiophene oligomers and polymers, THEOCHEM, 758, 29-39 (2006).
95. K.-T. Wong, C.-F. Wang, C. H. Chou, Y. O. Su, G.-H. Lee, S.-M. Peng, Synthesis and properties of novel thiophene-based conjugated homologues: 9,9-diphenylfluorene-capped oligothiophenes, Org. Lett., 4, 4439-4442 (2002).
96. V. Hernandez, H. Muguruma, S. Hotta, J. Casado, J. T. Lopez Navarrete, A combined spectroscopic and theoretical study of a series of aminomethyl end-capped oligothiophenes with potential applications in thin film devices, J. Phys. Chem. A, 104, 735-740 (2000).
97. S. E. Koh, B. Delley, J. E. Medvedeva, A. Facchetti, A. J. Freeman, T. J. Marks, M. A. Ratner, Quantum chemical analysis of electronic structure and n-and p-type charge transport in perfluoroarene-modified oligothiophene semiconductors, J. Phys. Chem. B, 110, 24361-24370 (2006).
98. A. Facchetti, M.-H. Yoon, C. L. Stern, H. E. Katz, T. J. Marks, Building blocks for n-type organic electronics: regiochemically modulated inversion of majority carrier sign in perfluoroarene-modified polythiophene semiconductors, Angew. Chem. Int. Ed., 42, 3900-3903 (2003).
99. A. Raya, M. A. Mora, Theoretical study of perfluorinated oligothiophenes: electronic and structural properties, Polymer, 45, 6391-6397 (2004).
100. G. Horowitz, B. Bachet, A. Yassar, P. Lang, F. Demanze, J. L. Fave, F. Garnier, Growth and characterization of sexithiophene single crystals, Chem. Mater., 7, 1337-1341 (1995).
101. Y. Sakamoto, S. Komatsu, T. Suzuki, Tetradecafluorosexithiophene: the first perfluorinated oligothiophene, J. Am. Chem. Soc., 123, 4643-4644 (2001).
102. W. R. Salaneck, O. Inganas, J.-O. Nilsson, J.-E. Osterholm, B. Themans, J. L. Bredas, Thermochromism in the poly(3-alkylthiophene)s: a study of conformational defects by photoelectron spectroscopy, Synth. Met., 28, 451-460 (1989);
103. H. Zhang, B. Yang, Y. Zheng, G. Yang, L. Ye, Y. Ma, X. Chen, G. Cheng, S. Liu, New biphenyl derivative with planar phenyl-phenyl conformation in crystal at room temperature exhibits highly efficient UV light-emitting, J. Phys. Chem. B, 108, 9571-9573 (2004);
104. J. Gierschner, H.-G. Mack, L. Luer, D. Oelkrug, Fluorescence and absorption spectra of oligophenylenevinylenes: vibronic coupling, band shapes and solvatochromism, J. Chem. Phys., 116, 8596-8609 (2002).
105. J. Gierschner, L. Liier, D. Oelkrug, E. Musluoglu, B. Behnisch, M. Hanack, Preparation and optical properties of oligophenylenevinylene/perhydrotriphenylene inclusion compounds, Adv. Mater., 12, 757-761 (2002).
106. M. J. Marsella, T. M. Swager, Designing conducting polymer-based sensors: selective ionochromic response in crown ether-containing polythiophenes, J. Am. Chem. Soc., 115, 12214-12215 (1993).
107. C. Roux, M. Leclerc, Rod-to-coil transition in alkoxy-substituted polythiophenes, Macromolecules, 25, 2141-2144 (1992);
108. N. Elmaci, E. Yurtsever, Thermochromism in oligothiophenes: the role of the internal rotation, J. Phys. Chem. A, 106, 11981-11986 (2002);
109. W. R. Salaneck, O. Inganas, B. Themans, J. O. Nilsson, B. Sjogren, J.-E. Österholm, J. L. Bredas, S. Svensson, Thermochromism in poly(3-hexylthiophene) in the solid state: a spectroscopic study of temperature-dependent conformational defects, J. Chem. Phys., 89, 4613-4619 (1988).
110. T. Oike, T. Kurata, K. Takimiya, T. Otsubo, Y. Aso, H. Zhang, Y. Araki, O. Ito, Polyether-bridged sexithiophene as a complexation-gated molecular wire for intramolecular photoinduced electron transfer, J. Am. Chem. Soc., 127, 15372-15373 (2005).
111. K. P. R. Nilsson, J. Rydberg, L. Baltzer, O. Inganas, Twisting macromolecular chains: self-assembly of a chiral supermolecule from nonchiral polythiophene polyanions and random-coil synthetic peptides, Proc. Natl. Acad. Sci. USA, 101, 11197-11202 (2004).
112. S. Samdal, E. J. Samuelsen, H. V. Volden, Molecular conformation of 2,2'-bithiophene determined by gas phase electron diffraction and ab initio calculations, Synth. Met., 59, 259-265 (1993);
113. M. Takayanagi, T. Gejo, I. Hanazaki, Geometry and torsional potential of 2,2'-bithiophene in a supersonic jet, J. Phys. Chem., 98, 12893-12898 (1994).
114. C. J. Tonzola, M. M. Alam, B. A. Bean, S. A. Jenekhe, New soluble n-type conjugated polymers for use as electron transport materials in light-emitting diodes, Macromolecules, 37, 3554-3563 (2004);
115. A. Wakamiya, D. Yamazaki, T. Nishinaga, T. Kitagawa, K. Komatsu, Synthesis and properties of novel oligothiophenes surrounded by bicyclo[2.2.2]octene frameworks, J. Org. Chem., 68, 8305-8314 (2003);
116. G. Gigli, F. Della Sala, M. Lomascolo, M. Anni, G. Barbarella, A. Di Carlo, P. Lugli, R. Cingolani, Photoluminescence efficiency of substituted quaterthiophene crystals, Phys. Rev. Lett., 86, 167-170 (2001);
117. G. Gigli, M. Lomascolo, R. Cingolani, G. Barbarella, M. Zambianchi, L. Antolini, F. Della Sala, A. Di Carlo, P. Lugli, Relationship between optical and structural properties in substituted quaterthiophene crystals, Appl. Phys. Lett., 73, 2414-2416 (1998).
118. P. Bauerle, Sulfur-containing oligomers, in Electronic Materials: the Oligomer Approach, ed. K. Müllen, G. Wegner, Wiley-VCH Verlag GmbH, Weinheim, 1998, pp. 105-197.
119. G. Zhang, Y. Pei, J. Ma, K. Yin, C.-L. Chen, Packing structures and packing effects on excitation energies of amorphous phase oligothiophenes, J. Phys. Chem. B, 108, 6988-6995 (2004).
120. P. Bucci, M. Longeri, C. A. Veracini, L. Lunazzi, Nematic phase nuclear magnetic resonance investigations of rotational isomerism. III. Conformational preferences and interconversion barrier of 2,2'-bithienyl, J. Am. Chem. Soc., 96, 1305-1309 (1974).
121. A. Alberti, L. Favaretto, G. Seconi, G. F. Pedulli, Radical cations and anions from some simple polythiophenes: an ESR investigation, J. Chem. Soc., Perkin Trans. 2, 931-935 (1990).
122. N. Di Cesare, M. Belletete, G. Durocher, M. Leclerc, Towards a theoretical design of thermochromic polythiophenes, Chem. Phys. Lett., 275, 533-539 (1997).
123. I. Levesque, M. Leclerc, Ionochromic and thermochromic phenomena in a regioregular polythiophene derivative bearing oligo(oxyethylene) side-chains, Chem. Mater., 8, 2843-2849 (1996).
124. N. Di Cesare, M. Belletete, C. Marrano, M. Leclerc, G. Dürocher, Intermolecülar interactions in conjugated oligothiophenes. 1. Optical spectra of terthiophene and substituted terthiophenes recorded in various environments, J. Phys. Chem. A, 103, 795-802 (1999);
125. N. Di Cesare, M. Belletete, M. Leclerc, G. Dürocher, Intermolecülar interactions in conjugated oligothiophenes. 2. Quantum chemical calculations performed on crystalline structures of terthiophene and substituted terthiophenes, J. Phys. Chem. A, 103, 803-811 (1999);
126. N. Di Cesare, M. Belletete, E. R. Garcia, M. Leclerc, G. Dürocher, Intermolecülar interactions in conjugated oligothiophenes. 3. Optical and photophysical properties of quaterthiophene and substituted quaterthiophenes in various environments, J. Phys. Chem. A, 103, 3864-3875 (1999).
127. H. Tachibana, N. Hosaka, Y. Tokura, Hysteretic thermochromism of regioregular poly(3-alkylthiophene) thin films, Macromolecules, 34, 1823-1827 (2001).
128. P. M. Viruela, R. Viruela, E. Orti, Difficulties of density functional theory in predicting the torsional potential of 2,2'-bithiophene, Int. J. Quantum Chem., 70, 303-312 (1998).
129. E. Orti, P. M. Viruela, J. Sanchez-Marin, F. Tomas, Ab initio determination of the geometric structure and internal rotation potential of 2,2'-bithiophene, J. Phys. Chem., 99, 4955-4963 (1995).
130. N. Di Cesare, M. Belletete, M. Leclerc, G. Dürocher, HF/3-21G*ab initio calculations on methoxy-sübstitüted bithiophenes, THEOCHEM, 467, 259-273 (1999).
131. F. Wudl, M. Kobayashi, A. J. Heeger, Poly(isothianaphthene), J. Org. Chem., 49, 3382-3384 (1984);
132. M. Kobayashi, N. Colaneri, M. Boysel, F. Wudl, A. J. Heeger, The electronic and electrochemical properties of poly(isothianaphthene), J. Chem. Phys., 82, 5717-5723 (1985);
133. N. Colaneri, M. Kobayashi, A. J. Heeger, F. Wudl, Electrochemical and opto-electrochemical properties of poly(isothianaphthene), Synth. Met., 14, 45-52 (1986).
134. J. L. Bredas, Relationship between bandgap and bond length alternation in organic conjugated polymers, J. Chem. Phys., 82, 3808-3811 (1985);
135. J. L. Bredas, B. Themans, J. M. Andre, A. J. Heeger, F. Wudl, Geometric and electronic structures of isothianaphthene and thieno[3,4-c]thiophene: a theoretical investigation, Synth. Met., 11, 343-352 (1985);
136. J. L. Bredas, A. J. Heeger, F. Wudl, Towards organic polymers with very small intrinsic bandgaps. I. Electronic structure of polyisothianaphthene and derivatives, J. Chem. Phys., 85, 4673-4678 (1986);
137. J. L. Bredas, Theoretical design of polymeric conductors, Synth. Met., 17, 115-121 (1987);
138. Y. S. Lee, M. Kertesz, The effect of heteroatomic substitutions on the bandgap of polyacetylene and poly(_p-phenylene) derivatives, J. Chem. Phys., 88, 2609-2617 (1988);
139. M. Kertesz, Y. S. Lee, Energy gap and bond length alternation in heterosübstitüted narrow gap semiconducting polymers, J. Phys. Chem., 91, 2690-2692 (1987);
140. Y. S. Lee, M. Kertesz, R. L. Elsenbaumer, Importance of energetics in the design of small bandgap conducting polymers, Chem. Mater., 2, 526-530 (1990);
141. A. Karpfen, M. Kertesz, Energetics and geometry of conducting polymers from oligomers, J. Phys. Chem., 95, 7680-7681 (1991);
142. J. Kürti, P. R. Surjan, M. Kertesz, Electronic structure and optical absorption of poly(biisothianaphthene-methine) and poly(isonaphthothiophene-thiophene): two low-bandgap polymers, J. Am. Chem. Soc., 113, 9865-9867 (1991);
143. J. Kürti, P. R. Surjan, Qüinoid vs aromatic structure of polyisothianaphthene, J. Chem. Phys., 92, 3247-3248 (1990);
144. E. Faülqües, W. Wallnofer, H. Küzmany, Vibrational analysis of heterocyclic polymers: a comparative stüdy of polythiophene, polypyrrole and polyisothianaphthene, J. Chem. Phys., 90, 7585-7593 (1989);
145. J. Geisselbrecht, J. Kürti, H. Küzmany, Effective conjugation coordinate model: an investigation of polythiophene and polyisothianaphthene, Synth. Met., 55-57, 4266-4271 (1993);
146. K. Nayak, D. S. Marynick, The interplay between geometric and electronic structures in polyisothianaphthene, polyisonaphthothiophene, polythieno(3,4-b)pyrazine and polythieno(3,4-b)qüinoxaline, Macromolecules, 23, 2237-2245 (1990);
147. I. Hoogmartens, P. Adriaensens, R. Carleer, D. Vanderzande, H. Martens, J. Gelan, An investigation into the electronic structure of poly(isothianaphthene), Synth. Met., 51, 219-228 (1992);
148. I. Hoogmartens, P. Adriaensens, D. Vanderzande, J. Gelan, C. Qüattrocchi, R. Lazzaroni, J. L. Bredas, Low-bandgap conjugated polymers. A joint experimental and theoretical stüdy of the structure of polyisothianaphthene, Macromolecules, 25, 7347-7356 (1992);
149. R. Kiebooms, I. Hoogmartens, P. Adriaensens, D. Vanderzande, J. Gelan, Low-bandgap conjugated polymers. Improved model compounds for the structural analysis of poly(isothianaphthene), Macromolecules, 28, 4961-4969 (1995);
150. G. Zerbi, M. C. Magnoni, I. Hoogmartens, R. Kiebooms, R. Carleer, D. Vanderzande, J. Gelan, On the quinoid structure of poly(isothianaphthene). A vibrational spectroscopic study, Adv. Mater., 7, 1027-1030 (1995).
151. P. M. Viruela, R. Viruela, E. Orti, J. L. Bredas, Geometric structure and torsional potential of biisothianaphthene. A comparative DFT and ab initio study, J. Am. Chem. Soc., 119, 1360-1369 (1997).
152. C. Quattrocchi, R. Lazzaroni, J. L. Bredas, R. Kiebooms, D. Vanderzande, J. Gelan, L. Van Meervelt, Optical absorption spectra of aromatic isothianaphthene oligomers: theory and experiment, J. Phys. Chem., 99, 3932-3938 (1995).
153. C. Aleman, J. Casanovas, Theoretical investigation of the 3,4-ethylenedioxythiophene dimer and unsubstituted heterocyclic derivatives, J. Phys. Chem. A, 108, 1440-1447 (2004).
154. S. S. Zade, M. Bendikov, Twisting and conjugated oligomers and polymers: case study of oligo-and polythiophene, Chem. Eur. J., 13, 3688-3700 (2007).
155. G. Raos, A. Famulari, V. Marcon, Computational reinvestigation of the bithiophene torsion potential, Chem. Phys. Lett., 379, 364-372 (2003).
156. J. Roncali, F. Garnier, R. Garreau, M. Lemaire, Reduction of the steric hindrance to conjugation in 3,4-disubstituted poly(thiophenes);cyclopenta[c]thiophene and thieno[c]thiophene as precursors of electrogener-ated conducting polymers, J. Chem Soc., Chem. Commun., 1500-1502 (1987).
157. M. Bednarz, P. Reineker, E. Mena-Osteritz, P. Bauerle, Optical absorption spectra of linear and cyclic thiophenes-selection rules manifestation, J. Lumin., 110, 225-231 (2004);
158. J. Kromer, P. Bauerle, Homologous series of regioregular alkylsubstituted oligothiophenes up to an 11-mer, Tetrahedron, 57, 3785-3794 (2001).
159. J. Serrano, J. Casado, V. Hernaindez, L. Favaretto, G. Distefano, J. T. Loipez Navarrete, Vibrational and theoretical DFT study of two regioregular methyl-disubstituted bithiophenes, J. Mol. Struct., 563-564, 539-544 (2001).
160. C. Moreno Castro, M. C. Ruiz Delgado, V. Hernandez, Y. Shirota, J. Casado, 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).
161. J. Casado, M. C. Ruiz Delgado, Y. Shirota, V. Hernandez, J. T. Lopez Navarrete, Computation and spec-troelectrochemistry as complementary tools for the study of electrochemically induced charged defects in 4-[bis(4-methylphenyl)amino]phenyl oligothiophenes as model systems for hole-transporting materials, J. Phys. Chem. B, 107, 2637-2644 (2003).
162. G. Zerbi, C. Castiglioni, M. Del Zoppo, Structure and optical properties of conjugated oligomers from their vibrational spectra, in Electronic Materials: the Oligomer Approach, ed. K. Müllen, G. Wegner, Wiley-VCH Verlag GmbH, Weinheim, 1998, pp. 345-402;
163. C. Castiglioni, J. T. Lopez Navarrete, G. Zerbi, M. Gussoni, A simple interpretation of the vibrational spectra of undoped, doped and photoexcited polyacetylene: amplitude mode theory in the GF formalism, Solid State Commun., 65, 625-630 (1988).
164. I. Harada, Y. Furukawa, Vibrational Spectra and Structure, Vol. 5, Elsevier, Amsterdam, 1991, pp. 369-469;
165. G. Louarn, J. P. Buisson, S. Lefrant, D. Fichou, Vibrational studies of a series of a-oligothiophenes as model systems of polythiophene, J. Phys. Chem, 99, 11399-11404 (1995).
166. J. Casado, M. Z. Zgierski, R. G. Hicks, D. J. T. Myles, P. M. Viruela, E. Orti, M. C. Ruiz Delgado, V. Hernandez, J. T. Lopez Navarrete, Mesitylthio-oligothiophenes in various redox states. Molecular and electronic views as offered by spectroscopy and theory, J. Phys. Chem. A, 109, 11275-11284 (2005).
167. E. Yurtsever, S. Kirmizialtin, Vibrational spectroscopy of structural defects in oligothiophenes, Mol. Phys., 101, 2725-2729 (2003).
168. F. Costanzo, D. Tonelli, G. Scalmani, J. Cornil, Theoretical investigation of the electronic and optical properties of oligothiophenes upon methyl, thiol and thiomethyl substitutions, Polymer, 47, 6692-6697 (2006).
169. G. G. Malliaras, J. K. Herrems, J. Wildeman, R. H. Wierings, S. S. Lampours, G. Hadziioannou, Tuning of the photo-and electroluminescence in multi-block copolymers of poly[(silanylene)thiophenes] via exciton confinement, Adv. Mater., 5, 721-723 (1993);
170. R. E. Gill, G. G. Malliaras, J. Wildeman, G. Hadziioannou, Tuning of photo-and electroluminescence in alkylated polythiophenes with well-defined regioregularity, Adv. Mater., 6, 132-135 (1994);
171. A. Hilberer, H.-J. Brouwer, B. J. van der Scheer, J. Wildeman, G. Hadziioannou, Synthesis and characterization of a new efficient blue-light-emitting copolymer, Macromolecules, 28, 4525-4529 (1995).
172. E. Zojer, J. Cornil, G. Leising, J. L. Bredas, Theoretical investigation of the geometric and optical properties of neutral and charged oligophenylenes, Phys. Rev. B, 59, 7957-7968 (1999).
173. A. Smie, A. Synowczyk, J. Heinze, R. Alle, P. Tschüncky, G. Götz, P. Bauerle, β,β-Disübstitüted oligothiophenes, a new oligomeric approach towards the synthesis of conducting polymers, J Electroanal Chem, 452, 87-95 (1998);
174. V. Barone, F. Lelj, N. Rüsso, M. Toscano, Conformational behavior of isomeric bithienyls. An ab initio stüdy, J. Chem. Soc., Perkin Trans. 2, 907-910 (1986).
175. U. Salzner, Theoretical investigation of excited states of oligothiophenes and of their monocations, J. Chem. Theory Comput., 3, 1143-1157 (2007).
176. S. S. Zade, M. Bendikov, unpublished work;for similar studies on oligo(phenylene vinylene) cation radicals, see V. M. Geskin, F. C. Grozema, L. D. A. Siebbeles, D. Beljonne, J. L. Bredas, J. Cornil, Impact of the computational method on the geometric and electronic properties of oligo(phenylene vinylene) radical cations J. Phys. Chem. B, 109, 20237-20243 (2005).
177. J. Casado, T. M. Pappenfus, L. L. Miller, K. R. Mann, E. Orti, P. M. Viruela, R. Poü-Amerigo, V. Hernandez, J. T. Loipez Navarrete, Nitro-functionalized oligothiophenes as a novel type of electroactive molecular material: spectroscopic, electrochemical and computational stüdy, J. Am. Chem. Soc., 125, 2524-2434 (2003).
178. J. Casado, L. L. Miller, K. R. Mann, T. M. Pappenfus, H. Higüchi, E. Orti, B. Milián, R. Poü-Amerigo, V. Hernaindez, J. T. Loipez Navarrete, Quinonoid oligothiophenes as electron-donor and electron-acceptor materials. A spectroelectrochemical and theoretical stüdy, J. Am. Chem. Soc., 124, 12380-12388 (2002).
179. J. Güay, P. Kasai, A. Diaz, R. Wü, J. M. Tour, L. H. Dao, Chain-length dependence of electrochemical and electronic properties of neutral and oxidized solüble a,a-coüpled thiophene oligomers, Chem. Mater., 4, 1097-1105 (1992);
180. P. Bauerle, U. Segelbacher, A. Maier, M. Mehring, Electronic structure of mono-and dimeric cation radicals in end-capped oligothiophenes, J. Am. Chem. Soc., 115, 10217-10223 (1993).
181. A. Berlin, S. Grimoldi, G. Zotti, R. M. Osüna, M. C. Rüiz Delgado, R. P. Ortiz, J. Casado, V. Hernandez, J. T. Lopez Navarrete, Synthesis and characterization of a novel terthiophene-based quinodimethane bearing a 3,4-ethylenedioxythiophene central ünit, J. Phys. Chem. B, 109, 22308-22318 (2005).
182. S. Hotta, K. Waragai, Alkyl-substituted oligothiophenes: crystallographic and spectroscopic studies of neutral and doped forms, J. Mater. Chem., 1, 835-842 (1991);
183. D. D. Graf, R. G. Düan, J. P. Campbell, L. L. Miller, K. R. Mann, From monomers to π-stacks. A comprehensive stüdy of the structure and properties of monomeric, π-dimerized and π-stacked forms of the cation radical of 3',4'-dibütyl-2,5"-diphenyl-2,2':5',2"-terthiophene, J. Am. Chem. Soc., 119, 5888-5899 (1997);
184. D. D. Graf, J. P. Campbell, K. R. Mann, L. L. Miller, Single-crystal X-ray structure of the cation radical of 3',4'-dibütyl-2,5"-diphenyl-2,2':5',2"-terthiophene: definitive evidence for π-stacked oxidized oligothiophenes, J. Am. Chem. Soc., 118, 5480-5481 (1996).
185. C. Aleman, L. Jülia, Characterization of the qüinoid structure for the 2,2'-bithiophene and 2,2',5',2"-terthiophene dications, J. Phys. Chem., 100, 14661-14664 (1996);
186. S. Irle, H. Lischka, Combined ab initio and density functional study on polaron to bipolaron transitions in oligophenyls and oligothiophenes, J. Chem. Phys., 107, 3021-3031 (1997);
187. G. Moro, G. Scalmani, U. Cosentino, D. Pitea, On the structure of bipolaronic defects in thiophene oligomers: a density functional stüdy, Synth. Met., 92, 69-73 (1998).
188. D. E. Janzen, M. W. Bürand, P. C. Ewbank, T. M. Pappenfus, H. Higüchi, D. A. da Silva Filho, V. G. Young, J. L. Bredas, 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).
189. J. L. Bredas, J. P. Calbert, D. A. da Silva Filho, J. Cornil, Organic semiconductors: a theoretical characterization of the basic parameters governing charge transport, Proc. Natl. Acad. Sci. USA, 99, 5804-5809 (2002).
190. J. Cornil, J. P. Calbert, D. Beljonne, R. Silbey, J. L. Bredas, Charge transport versus optical properties in semiconducting crystalline organic thin films, Adv. Mater., 12, 978-983 (2000).
191. G. Führmann, T. Debaerdemaeker, P. Bauerle, Carbon-carbon bond formation through oxidatively induced elimination of platinum complexes: a novel approach to conjugated macrocycles, Chem. Commun., 948-949 (2003);
192. J. Kromer, I. Rios-Carreras, G. Führmann, C. Müsch, M. Wünderlin, T. Dabaerde-maeker, E. Mena-Osteritz, P. Bauerle, Synthesis of the first fülly π-conjugated macrocyclic oligothiophenes: cyclo[n]thiophenes with tunable cavities in the nanometer regime, Angew. Chem. Int. Ed., 39, 3481-3486 (2000).
193. E. Mena-Osteritz, P. Bauerle, Self-assembled hexagonal nanoarrays of novel macrocyclic oligothiophene-diacetylenes, Adv. Mater., 13, 243-246 (2001);
194. E. Mena-Osteritz, Superstructures of self-organizing thiophenes, Adv. Mater., 14, 609-616 (2002);
195. J. Casado, V. Hernandez, R. P. Ortiz, M. C. Ruiz Delgado, J. T. Lopez Navarrete, G. Fuhrmann, P. Bauerle, Application of Raman spectroscopy and quantum chemistry for featuring the structure of positively charged species in macrocyclic π-conjugated diacetylene-bridged oligothiophenes, J. Raman Spectrosc., 35, 592-599 (2004).
196. J. Casado, M. Z. Zgierski, G. Fuhrmann, P. Bauerle, J. T. Lopez Navarrete, Structural implications of ring shape, dimension and metal atom insertion in nanosized cyclic oligothiophenes: joint Raman and density functional theory study, J. Chem. Phys., 125, 044518-1-044518-9 (2006).
197. S. S. Zade, M. Bendikov, Cyclic oligothiophenes: novel organic materials and models for polythiophene. A theoretical study, J. Org. Chem., 71, 2972-2981 (2006).
198. H. Cao, J. Ma, G. Zhang, Y. Jiang, Borole/thiophene cooligomers and copolymers with quinoid structures and biradical characters, Macromolecules, 38, 1123-1130 (2005).
199. S. Fomine, P. Guadarrama, Oligothiophene catenanes and knots: a theoretical study, J. Phys. Chem. A, 110, 10098-10105 (2006);
200. S. Fomine, P. Guadarrama, P. Flores, Oligothiophene catenanes and knots. Part II. Mono and dications. A theoretical study, J. Phys. Chem. A, 111, 3124-3131 (2007).
201. R.-F. Chen, J.-F. Pan, J.-H. Pan, Y. Zhang, Q.-L. Fan, W. Huang, Theoretical investigation of the tunable behavior of p-n copolymers based on oligothiophenes and 1,4-bis(oxadiazolyl)-benzene, J. Phys. Chem. B, 110, 23750-23755 (2006).
202. W.-L. Yu, M. Hong, J. Pei, W. Huang, Tuning redox behavior and emissive wavelength of conjugated polymers by p-n diblock structures, J. Am. Chem. Soc., 120, 11808-11809 (1998);
203. J. F. Pan, S. J. Chua, W. Huang, Tuning redox behavior and emissive wavelength of conjugated polymers by p-n diblock structures-a theoretical investigation, Synth. Met., 110, 85-89 (2000);
204. M. K. Ng, L. P. Yu, Synthesis of amphiphilic conjugated diblock oligomers as molecular diodes, Angew. Chem. Int. Ed., 41, 3598-3601 (2002);
205. A. S. Fisyuk, R. Demadrille, C. Querner, M. Zagorska, J. Bleuse, A. Pron, Mixed alkylthiophene-based heterocyclic polymers containing oxadiazole units via electrochemical polymerization: spectroscopic, electrochemical and spectroelectrochemical properties, New. J. Chem., 29, 707-713 (2005).
206. X. Zhou, A.-M. Ren, J.-K. Feng, Theoretical investigation on the ground-and excited-state properties of novel octupolar oligothiophene-functionalized truxenes and dipolar analogs, Polymer, 45, 7747-7757 (2004).
207. A. Facchetti, M.-H. Yoon, C. L. Stern, G. R. Hutchison, M. A. Ratner, T. J. Marks, Building blocks for n-type molecular and polymeric electronics. Perfluoroalkyl-versus alkyl-functionalized oligothiophenes (nTs;n = 2-6). Systematic synthesis, spectroscopy, electrochemistry and solid-state organization, J. Am. Chem. Soc., 126, 13480-13501 (2004).
208. R. P. Ortiz, M. C. Ruiz Delgado, J. Casado, V. Hernandez, O.-K. Kim, H. Y. Woo, J. T. Lopez Navarrete, Electronic modulation of dithienothiophene (DTT) as π-center of D-π-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).