Evidence of quinonoid structures in the vibrational spectra of thiophene based conducting polymers: Poly(thiophene), poly(thieno[3,4-6]benzene), and poly(thieno[3,4-b]pyrazine)

Journal of Chemical Physics

Volumn 106, Issue 13, 1997, Pages 5541-5553

  Cuff, Lilee ^a   Kertesz, Miklos ^a  

^a GEORGETOWN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001228943     PISSN: 00219606     EISSN: None     Source Type: Journal    
DOI: 10.1063/1.473576     Document Type: Article

References (64)

1. G. L. Baker, in Electronic and Photonic Applications of Polymers, ACS Adv. in Chemistry Series 210, edited by M. J. Bowden and S. R. Turner (American Chemical Society, Washington, D.C., 1988), p. 271.
2. C. Yong, and R. Renyuan, Solid State Commun. 54, 211 (1985).
3. (a) P. N. Prasad, J. Swiatkiewicz, and J. Pfleger, Mol. Cryst. Liquid Cryst. 160, 53 (1988);
4. (b) T. Sugiyama, T. Wada, and H. Sasabe, Synth. Met. 28, C323 (1989).
5. J. Roncali, Chem. Rev. 92, 711 (1992).
6. F. Wudl, M. Kobayashi, and A. J. Heeger, J. Org. Chem. 36, 3382 (1984).
7. (a) M. Pomerantz, B. Chaloner-Gill, L. O. Harding, J. J. Tseng, and W. J. Pomerantz, J. Chem. Soc. Chem. Commun. 1992, 1672
8. (b) M. Kobayashi, N. Colaneri, M. Boysel, F. Wudl, and A. J. Heeger, J. Chem. Phys. 82, 5717 (1985).
9. (a) Y. S. Lee and M. Kertesz, J. Chem. Phys. 88, 2609 (1988);
10. (b) Int. J. Quantum Chem. Quantum Chem. Symp. 21, 163 (1987).
11. Y. Ikenoue, F. Wudl, and A. J. Heeger, Synth. Met. 40, 1 (1991).
12. (a) C. X. Cui and M. Kertesz, J. Chem. Phys. 93, 5257 (1990);
13. (b) L. Cuff, C. X. Cui, and M. Kertesz, J. Am. Chem. Soc. 116. 9269 (1994).
14. (a) Ch. Ehrendorfer and A. Karpfen, J. Phys. Chem. 99, 5341 (1995);
15. (b) Vibrational Spectrosc. 8, 293 (1995).
16. (a) M. Akimoto, Y. Furukawa, H. Takeuchi, and I. Harada, Synth. Met. 15, 353 (1986);
17. (b) Y. Furukawa, M. Akimoto, and I. Harada, ibid. 18, 151 (1987);
18. (c) M. Kofranek, T. Kovar, H. Lischka, and A. Karpfen, J. Mol. Struct. Theochem 259, 181 (1992);
19. (d) J. T. Lopez Navarrete and G. Zerbi, J. Chem. Phys. 94, 965 (1991);
20. (e) J. L. Sauvajol, D. Chenouni, J. P. Lere-Porte, C. Chorro, B. Moukala, and J. Petrissans, Synth. Met. 38, 1 (1990);
21. (f) Z. Vardeny, E. Ehrenfreund, O. Brafman, A. J. Heeger, and F. Wudl, ibid. 18, 183 (1987).
22. G. Louarn, J. Y. Mevellec, J. P. Buisson, and S. Lefrant, J. Chim. Phys 89, 987 (1992).
23. Y. Furukawa, N. Yokonuma, M. Tasumi, M. Kuroda, and J. Nakayama, Mol. Cryst. Liquid Cryst. 256, 113 (1994).
24. J. L. Bredas, B. Themans, J. G. Fripiat, J. M. Andre, and R. R. Chance, Phys. Rev. B 29, 6761 (1984).
25. A. Karpfen and M. Kertesz, J. Phys. Chem. 95, 7680 (1991).
26. M. Kertesz, Synth. Met. 69, 641 (1995).
27. J. Kurti, P. R. Surjan, and M. Kertesz, J. Am. Chem. Soc. 113, 9865 (1991).
28. K. Nayak and D. S. Marynick, Macromolecules 73, 2237 (1990).
29. J. Kastner, H. Kuzmany, D. Vegh, M. Landl, L. Cuff, and M. Kertesz, Macromolecules 28, 2922 (1995).
30. I. Hoogmartens, P. Adriensens, D. Vanderzande, J. Gelan, C. Quattrocchi, R. Lazzaroni, and J. L. Bredas, Macromolecules 25, 7347 (1992).
31. J. Kurti and P. R. Surjan, J. Chem. Phys. 92, 3247 (1990).
32. L. Cuff, M. Kertesz, J. Geisselbrecht, J. Kurti, and H. Kuzmany, Synth. Met. 55, 564 (1993).
33. E. Faulques, W. Wallnofer, and H. Kuzmany, J. Chem. Phys. 90, 7585 (1989).
34. I. Hoogmartens, D. Vanderzande, and H. Martens, Synth. Met. 14/1-2, 513 (1991).
35. E. B. Wilson, Jr., J. C. Decius, and P. C. Cross, Molecular Vibrations (McGraw-Hill, New York, 1995).
36. H. Tadokoro, Structure of Crystalline Polymers (Wiley, New York, 1979).
37. See, for example, P. C. Painter, M. M. Coleman, and J. L. Koenig, The Theory of Vibrational Spectroscopy and its Applications to Polymeric Materials (Wiley, New York, 1982).
38. F. J. Ramirez, V. Hernandez, and J. T. Lopez Navarrete, J. Comput. Chem. 15, 405 (1994).
39. C. W. Bock, Y. N. Panchenko, and V. I. Pupyshev, J. Comput. Chem. 11, 623 (1990).
40. L. Cuff and M. Kertesz, Macromolecules 27, 762 (1994).
41. L. Cuff and M. Kertesz, J. Phys. Chem. 98, 12 223 (1994).
42. C. X. Cui, M. Kertesz, and H. Eckhardt, Synth. Met. 41-43, 3491 (1991).
43. M. Kofranek, H. Lischka, and A. Karpfen, J. Chem. Phys. 96, 982 (1992).
44. J. A. Pople, H. B. Schlegel, R. Krishnan, D. S. Defrees, J. S. Binkley, M. J. Frisch, R. A. White, R. F. Hout, and W. J. Hehre, Int. J. Quantum Chem. Quantum Chem. Symp. 15, 267 (1981).
45. P. Pulay, G. Fogarasi, and J. E. Boggs, J. Chem. Phys. 74, 3999 (1981).
46. G. Fogarasi and P. Pulay, Vibrational Spectra and Structure, edited by J. R. Durig (Elsevier, Amsterdam, 1985), Vol. 14, pp. 125-219.
47. Ch. Ehrendorfer and A. Karpfen, J. Phys. Chem. 99, 10 196 (1995).
48. M. Kofranek, T. Kovar, A. Karpfen, and H. Lishka, J. Chem. Phys. 96, 4464 (1992).
49. P. Pulay, G. Fogarasi, F. Pang, and J. E. Boggs, J. Am. Chem. Soc. 101, 2550 (1979).
50. (a) M. J. Frisch, M. Head-Gordon, G. W. Trucks, J. B. Foresman, H. B. Schlegel, K. Raghavachari, M. A. Robb, J. S. Binkley, C. Gonzalez, D. J. Defrees, D. J. Fox, R. A. Whiteside, R. Seeger, C. S. Melius, J. Baker, R. L. Martin, L. R. Kahn, J. J. P. Stewart, S. Topiol, and J. Pople, GAUSSIAN 90, Gaussian Inc., Pittsburgh, Pennsylvania, 1990;
51. (b) M. J. Frisch, M. Head-Gordon, G. W. Trucks, P. M. Gill, M. W. Wong, J. B. Foresman, B. G. Johnson, H. B. Schlegel, M. A. Robb, E. S. Replogle, R. Gomperts, J. L. Andres, K. Raghavachari, J. S. Binkley, C. Gonzalez, R. L. Martin, D. J. Fox, D. J. Defrees, J. Baker, J. J. P. Stewart, and J. Pople, GAUSSIAN 92, Gaussian Inc., Pittsburgh, Pennsylvania, 1992.
52. R. M. Badger, J. Chem. Phys. 2, 128 (1934).
53. R. M. Badger, J. Chem. Phys. 3, 193 (1935).
54. P. Pulay, G. Fogarasi, J. E. Boggs, and A. Vargha, J. Am. Chem. Soc. 105, 7037 (1983).
55. G. Fogarasi, P. G. Szalay, P. P. Liescheski, J. E. Boggs, and P. Pulay, J. Mol. Struct. 151, 341 (1987).
56. W. D. Allen, A. G. Csaszar, and D. A. Horner, J. Am. Chem. Soc. 114, 6834 (1992).
57. D. Damiani, L. Ferretti, and E. Gallinella, Chem. Phys. Lett. 37, 265 (1976).
58. V. K. Belsky, V. E. Zavodnik, and V. M. Vozzhennikov, Acta Crystallogr. C 40, 1210 (1984).
59. A. Langseth and P. B. Stoicheff, Can. J. Phys. 34, 350 (1956).
60. J. M. Orza, M. Rico, and F. J. Biarge, J. Mol. Spectrosc. 19, 188 (1966).
61. B. Bak, D. Christensen, L. Hansen-Nygaard, and J. Rastrup-Andersen, J. Mol. Spectrosc. 7, 58 (1961).
62. G. Zerbi, M. Gussoni, and C. Castiglioni, in Conjugated Polymers, edited by J. L. Bredas and R. Silbey (Kluwer, Netherlands, 1991), p. 435.
63. G. Zerbi and B. Chierichetti, J. Chem. Phys. 94, 4637 (1991).
64. C. Castiglioni, M. Del Zoppo, and G. Zerbi, J. Raman Spectrosc. 24, 485 (1993).