Theoretical study of the structure and torsional potential of pyrrole oligomers

Journal of the Chemical Society - Faraday Transactions

Volumn 94, Issue 1, 1998, Pages 25-32

  Millefiori, Salvatore ^a   Alparone, Andrea ^a  

^a UNIVERSITY OF CATANIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748596859     PISSN: 09565000     EISSN: None     Source Type: Journal    
DOI: 10.1039/a705780f     Document Type: Article

References (74)

1. A. O. Patil, A. J. Heeger and F. Wudl, Chem. Rev., 1988, 88, 183.
2. A. J. Heeger, S. Kivelson, J. R. Schrieffer and W-P. Su, Rev. Mod. Phys., 1988, 60, 781.
3. Nonlinear Optical Properties of Polymers, ed. A. J. Heeger, J. Orenstein and D. R. Ulrich, MRS Symposia Proceedings N.109, Materials Research Society, Pittsburgh, 1988.
4. Handbook of Conducting Polymers, ed. T. A. Skotheim, Marcel Dekker, New York, 1986, vol. 1 and 2.
5. Conjugated Polymeric Materials: Opportunities in Electronics, Optoelectronics and Molecular Electronics, ed. J. L. Brédas and R. R. Chance, NATO ASI Ser. E, Vol. 182, Kluwer, Dordrecht, 1990.
6. (a) V. Hernandez, C. Castiglioni, M. Del Zoppo and G. Zerbi, Phys Rev. B, 1994, 50, 9815, and references therein;
7. (b) R. H. Baughman and R. R. Chance, J. Poym. Sci. Polym. Phys. Ed., 1976, 14, 2037;
8. (c) G. N. Patel, R. R. Chance and J. D. Witt, J. Chem. Phys., 1979, 70, 4387;
9. (d) G. Wenz, M. A. Muller, M. Schmidt and G. Wegner, Macromolecules, 1984, 17, 837;
10. (e) G. Zerbi, M. Veronelli, S. Martina, A-D. Schlüter and G. Wegner, Adv. Mater., 1994, 6, 385.
11. (a) A. F. Diaz, K. K. Kanazawa and G. P. Gardini, J. Chem. Soc., Chem. Commun., 1988, 183;
12. (b) K. K. Kanazawa, A. F. Diaz, R. H. Geiss, W. D. Gill, J. F. Kwak, J. A. Logan, J. F. Rabolt and G. B. Street, J. Chem. Soc., Chem. Commun., 1979, 635;
13. (c) K. K. Kanazawa, A. F. Diaz, W. D. Gill, P. H. Grant, G. B. Street, G. P. Gardini and J. F. Kwak, Synth. Met., 1980, 1, 329.
14. L. A. Prezyna, Y. J. Qiu, J. R. Reynolds and G. E. Wnek, Macromolecules, 1991, 24, 5283.
15. S. K. Ghoshal, Chem. Phys. Lett., 1989, 158, 65.
16. B. Z. Lubentsov, G. I. Zvereva, Ya. H. Samovarov, S. M. Bystriak, O. N. Timofeeva and M. L. Khidekel, Synth. Met., 1991, 41, 1143.
17. (a) T. C. Pearce, J. W. Gardner, S. Friel, P. N. Bartlett and N. Blair, Analyst, 1993, 118, 371;
18. (b) B. P. J. de Lacy Costello, P. Evans, R. J. Ewen, C. L. Honeybourne and N. M. Ratcliffle, J. Mater. Chem., 1996, 6, 289;
19. (c) P. Evans, N. M. Ratcliffe, J. R. Smith and S. A. Campbell, J. Mater. Chem., 1996, 6, 295.
20. P. R. Teasdale and G. G. Vallace, Analyst, 1993, 118, 329.
21. E. V. Thillo, G. Defieuw and W. de Winter, Bull. Soc. Chim. Belg., 1990, 99, 981.
22. C. J. Gow and C. F. Zukoski, J. Colloid Interface Sci., 1990, 136, 175.
23. T. Sata, T. Yamaguchi and K. Matsusaki, J. Phys., Chem., 1996, 100, 16633.
24. G. C. Teare and N. M. Ratcliffe, J. Mater. Chem., 1996, 6, 301.
25. S. Martina, U. Enkelmann, A-D. Schlüter and G. Wegner, Synth. Met., 1991, 41, 403.
26. L. Groenendaal, H. W. I. Peerlings, J. L. T. vanDogen, E. E. Havinga, J. A. J. M. Vekemans and E. W. Meijer, Macromolecules, 1995, 28, 116.
27. L. Nygaard, J. T. Nielsen, J. Kirchheiner, G. Maltesen, J. Rastrup-Andersen and G. O. Sørensen, J. Mol. Struct., 1969, 3, 491.
28. (a) J. L. Brédas, R. Silbey, D. S. Boudreaux and R. R. Chance, J. Am. Chem. Soc., 1983, 105, 6555;
29. (b) J-M. André, D. P. Vercauteren, G. B. Street and J. L. Brédas, J. Chem. Phys., 1984, 80, 5643;
30. (c) J. L. Brédas, G. B. Street, B. Thémans and J-M. André, J. Chem. Phys., 1985, 83, 1323;
31. (d) D. Beljonne and J. L. Brédas, Phys. Rev. B, 1994, 50, 2841;
32. (e) A. K. Bakhshi Poia, J. Chem. Soc., Faraday Trans., 1996, 92, 2281.
33. G. Rossi, R. R. Chance and R. Silbey, J. Chem. Phys., 1989, 90, 7594.
34. (a) M. Kofranek, T. Kovár, A. Karpfen and H. Lischka, J. Chem. Phys., 1992, 96, 4464;
35. (b) B. Tian and G. Zerbi, J. Chem. Phys., 1990, 92, 3886;
36. (c) E. Faulques, W. Wallnöfer and H. Kuzmany, J. Chem. Phys., 1989, 90, 7585;
37. (d) R. Kostić, D. Raković, S. A. Stepanyan, I. E. Davidova and L. A. Gribov, J. Chem. Phys., 1995, 102, 3104;
38. (e) G. Zerbi, M. Veronelli, S. Martina, A-D. Schlüter and G. Wegner, J. Chem. Phys., 1994, 100, 978.
39. (a) Y. Verbandt, H. Thiepont, I. Veretennicoff and P. Geerlings, Chem. Phys. Lett., 1996, 251, 47;
40. (b) J. L. Toto, T. T. Toto and C. P. de Melo, Chem. Phys. Lett., 1995, 245, 660;
41. (c) J. L. Toto, T. T. Toto, C. P. de Melo and K. A. Robins, J. Chem. Phys., 1995, 102, 8048;
42. (d) V. Keshari, M. K. P. Wijekoon, P. N. Prasad and S. P. Karna, J. Phys. Chem., 1995, 99, 9045;
43. (e) A. Hinchliffe and M. H. J. Soscún, J. Mol. Struct. (THEOCHEM), 1995, 331, 109;
44. (f) Y. Matsuzaki, M. Nakano, K. Yamaguchi, T. Tanaka and T. Yamabe, Chem. Phys. Lett., 1996, 263, 119.
45. (a) E. D. Simandiras, N. C. Handy and R. D. Amos, J. Phys. Chem., 1988, 92, 1739;
46. (b) P. I. Nagy, G. J. Durant and D. A. Smith, J. Am. Chem. Soc., 1993, 115, 2912;
47. (c) N. El-Bakali Kassimi, R. J. Doerksen and A. J. Thakkar, J. Phys. Chem., 1995, 99, 12790;
48. (d) S. Y. Lee and B. H. Boo, J. Phys. Chem., 1996, 100, 15078.
49. E. Ortí, J. Sánchez-Marín and F. Tomás, Theor. Chim. Acta, 1986, 69, 41.
50. L. Padilla-Campos and A. Toro-Labbè, J. Mol. Struct. (THEOCHEM), 1995, 330, 223.
51. (a) V. Galasso and N. Trinajstic, Tetrahedron, 1972, 28, 4419;
52. (b) E. Ortí, F. Tomás and J. Sánchez-Marín, J. Mol. Spectrosc., 1983, 104, 197;
53. (c) J. T. Lopez Navarrete, B. Tian and G. Zerbi, Synth. Met., 1990, 38, 299;
54. (d) S. Y. Hong, S. J. Kwon, S. C. Kim and D. S. Marynick, Synth. Met., 1995, 69, 701;
55. (e) S. Y. Hong, Bull. Korean Chem. Soc., 1995, 16, 845;
56. (f) M. Breza and V. Laurinc, Macromol. Theory Simul., 1996, 5, 107;
57. (g) R. J. Waltman and J. Bargon, Tetrahedron, 1984, 40, 3963;
58. (h) E. Yurtsever and B. Erman, Polymer, 1993, 34, 3887.
59. K. Burke, J. P. Perdew and M. Levy, Modern Density Functional Theory: A Tool for Chemistry, ed. J. M. Seminario and P. Politzer, Elsevier, Amsterdam, 1994.
60. (a) Density Functional Methods in Chemistry, ed. J. Lobanowski and J. W. Andzelm, Springer-Verlag, New York, 1991;
61. (b) N. Oliphant and R. J. Bartlett, J. Chem. Phys., 1994, 100, 6550.
62. J. R. Smith, P. A. Cox, S. A. Campbell and N. M. Ratcliffe, J. Chem. Soc., Faraday Trans., 1995, 91, 2331.
63. GAUSSIAN 94, Revision B.1, M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. A. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart M. Head-Gordon C. Gonzales and J. A. Pople, Gaussian, Inc., Pittsburg PA, 1995.
64. A. D. Becke, J. Chem. Phys., 1993, 98, 5648.
65. C. Lee, W. Yang and R. G. Parr, Phys. Rev. B, 1988, 37, 785.
66. (a) Internal Rotation in Molecules, ed. W. J. Orville-Thomas, J. Wiley, London, 1974;
67. (b) L. Radom and J. A. Pople, J. Am. Chem. Soc., 1970, 92, 4786.
68. L. Salem, The Molecular Orbital Theory of Conjugated Systems, Benjamin, New York, 1966.
69. E. Ortí, P. M. Viruela, J. Sánchez-Marín and F. Tomás, J. Phys. Chem., 1995, 99, 4955.
70. S. Millefiori and A. Alparone, in preparation.
71. G. J. Pyrka and Q. Fernando, Acta Crystallogr., Sect. C, 1988, 44, 562.
72. S. Samdal, E. J. Samuelsen and H. V. Volden, Synth. Met., 1993, 59, 259.
73. V. Hernandez and J. T. Lopez-Navarrete, J. Chem. Phys., 1994, 101, 1369.
74. M. Ciofalo and G. La Manna, Chem. Phys. Lett., 1996, 263, 73.