Towards Designing Environmentally Stable Conjugated Polymers with very Small Band-Gaps

Bulletin of the Korean Chemical Society

Volumn 24, Issue 11, 2003, Pages 1649-1654

  Hong, Sung Y ^a   Kim, Sung C ^a  

^a Kosin University   (South Korea)

Author keywords

Aromaticity; Nucleus independent chemical shifts; Quantum chemical investigation; Small band gap polymers; Stabilization energy

Indexed keywords

AROMATIC COMPOUND; AZULENE DERIVATIVE; PENTAFULVALENE DERIVATIVE; POLYMER; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CHEMICAL REACTION; CONDUCTOR; CONJUGATION; ELECTRON TRANSPORT; MOLECULAR STABILITY; QUANTUM CHEMISTRY; SEMICONDUCTOR;

EID: 0347004671     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: 10.5012/bkcs.2003.24.11.1649     Document Type: Article

References (64)

1. Hong, S. Y.; Lee, K. W. Chem. Mater. 2000, 12, 155.
2. Hong, S. Y. Chem. Mater. 2000, 12, 495.
3. Doering, W. v. E. Theoretical Organic Chemistry; Butterworth; London, 1959; p 35. Matzner, E. Ph. D. Thesis; Yale University: 1958.
4. Dewar, M. J. S.; Gleicher, G. J. J. Am. Chem. Soc. 1965, 87, 685; 692.
5. Dewar, M. J. S.; de Llano, C. J. Am. Chem. Soc. 1969, 91, 789.
6. Hess, B. A., Jr.; Schaad, L. J. J. Am. Chem. Soc. 1971, 93, 305; 2413.
7. Hess, B. A., Jr.; Schaad, L. J. J. Org. Chem. 1971, 36, 3418.
8. Aihara, J. J. Am. Chem. Soc. 1976, 98, 2750; 1977, 99, 2048.
9. Aihara, J. J. Am. Chem. Soc. 1976, 98, 2750; 1977, 99, 2048.
10. Gutman, I.; Milun, M.; Trinajstic, N. J. Am. Chem. Soc. 1977, 99, 1692.
11. Schaad, L. J.; Hess, B. A., Jr. Chem. Rev. 2001, 101, 1465.
12. Neuenschwander, M. In The Chemistry of Functional Groups. Supplement A. The Chemistry of Double-Bonded Functional Groups; Patai, S., Ed.; Wiley: Chichester, 1989; Vol. 2, pp 1131-1268.
13. McAllister, M. A.; Tidwell, T. T. J. Am. Chem. Soc. 1992, 114, 5362.
14. Julg, A.; Francois, P. Theor. Chim. Acta 1967, 7, 249.
15. Kruszewski, J.; Krygowski, T. M. Bull. Acad. Pol. Sci., Ser. Sci. Chim. 1972, 20, 907.
16. Elvidge, J. L.; Jackman, L. M. J. Chem. Soc. 1961, 859.
17. Neuenschwander, M.; Bönzli, P. Helv. Chim. Acta 1991, 74, 1823.
18. Fowler, P.; Steiner, E. J. Phys. Chem. A 1997, 101, 1409.
19. Bader, R. F. W.; Keith, T. A. J. Chem. Phys. 1993, 99, 3683.
20. Fleischer, U.; Kutzelnigg, W.; Lazzeretti, P.; Müllenkamp, V. J. Am. Chem. Soc. 1994, 116, 5298.
21. Schleyer, P. v. R.; Jiao, H. Pure Appl. Chem. 1996, 28, 209.
22. Schleyer, P. v. R.; Maerker, C.; Dransfeld, A.; Jiao, H.; Hommes, N. J. R. v. E. J. Am. Chem. Soc. 1996, 118, 6317.
23. Mark, V. Tetrahedron Lett. 1961, 333.
24. Ginsberg, A. E.; Paatz, R.; Korte, F. Tetrahedron Lett. 1962, 779.
25. Kwistowski, P. T.; West, R. J. Am. Chem. Soc. 1966, 88, 4541.
26. Fallon, L.; Ammon, H. L.; West, R.; Rao, V. N. M. Acta Crystallogr. B 1974, 30, 2407.
27. Prinzbach, H.; Sauter, H. Angew. Chem. Int. Ed. Engl. 1972, 11, 133.
28. Burk, P.; Abboud, J.-L.; Koppel, I. A. J. Phys. Chem. 1996, 100, 6992.
29. Veszprémi, T.; Takahashi, M.; Hajgató, B.; Ogasawara, J.; Sakamoto, K.; Kira, M. J. Phys. Chem. A 1998, 102, 10530.
30. Abboud, J.-L. M.; Castaño, O.; Herreros, M.; Leito, I.; Notario, R.; Sak, K. J. Org. Chem. 1998, 63, 8995.
31. Nyulászi, L.; Schleyer, P. v. R. J. Am. Chem. Soc. 1999, 121, 6872.
32. Balci, M.; Mckee, M. L.; Schleyer, P. v. R. J. Phys. Chem. A 2000, 104, 1246.
33. Hess, B. A., Jr.; Schaad, L. J. Israel J. Chem. 1978, 17, 155.
34. (a) Hohenberg, P.; Kohn, W. Phys. Rev. 1964, 136, B864.
35. (b) Kohn, W.; Sham, I. J. Phys. Rev. 1965, 140, A1133.
36. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
37. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Retersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanatakara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, N. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98 (Revision A.9); Gaussian; Inc.: Pittsburgh, PA, 1998.
38. Hehre, W. J.; Ditchfield, R.; Radom, L.; Pople, J. A. J. Am. Chem. Soc. 1970, 92, 4796.
39. George, P.; Trachtman, M.; Bock, C. W.; Brett, A. M. Theoret. Chim. Acta(Berl.) 1975, 38, 121.
40. George, P.; Trachtman, M.; Bock, C. W.; Brett, A. M. J. Chem. Soc. Perkin II 1976, 1222.
41. George, P.; Trachtman, M.; Brett, A. M.; Bock, C. W. J. Chem. Soc. Perkin II 1977, 1036.
42. Schleyer, P. v. R.; Jiao, H.; Hommes, N. J. R. v. E.; Malkin, V. G.; Malkina, O. I. J. Am. Chem. Soc. 1997, 119, 12669.
43. West, R.; Buffy, J. J.; Haaf, M.; Müller, T.; Gehrhus, B.; Lappert, M. F.; Apeloig, Y. J. Am. Chem. Soc. 1998, 120, 1639.
44. (a) Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902.
45. (b) Stewart, J. J. P. QCPE Bull. 1985, 5, 62.
46. (c) Cui, C. X.; Kertesz, M. J. Am. Chem. Soc. 1989, 111, 4216.
47. Hong, S. Y.; Kim, D. Y.; Kim, C. Y.; Hoffmann, R. Macromolecules 2001, 34, 6476.
48. Hong, S. Y.; Marynick, D. S. J. Chem. Phys. 1992, 96, 5497.
49. (a) Hong, S. Y.; Song, J. M. J. Chem. Phys. 1997, 107, 10607.
50. Hong, S. Y. Bull. Korean Chem. Soc. 1999, 20, 42.
51. (b) See the following references to compare the MEH predictions and experimental measurements for polysilole: Yamagauchi, S.; Goto, T.; Tamao, K. Angew. Chem. Int. Ed. Engl. 2000, 39, 1695.
52. Hong, S. Y.; Kwon, S. J.; Kim, S. C. J. Chem. Phys. 1996, 104, 1140.
53. Hong, S. Y.; Song, J. M. Synth. Met. 1997, 85, 1113.
54. (c) See the following references to compare the MEH predictions and the experimental measurements for poly(thieno[3,4-b]thiophene): Lee, K.; Sotzing, G. A. Macromolecules 2001, 34, 5746.
55. Pomerantz, M.; Gu, X. Synth. Met. 1997, 84, 243.
56. Hong, S. Y.; Marynick, D. S. Macromolecules 1992, 25, 4652.
57. Lias, S. G.; Bartmess, J. E.; Liebman, J. F.; Holmes, J. L.; Levin, R. D.; Mallard, W. G. J. Phys. Chem. Ref. Data 1988, 17, Suppl. 1.
58. Martin, J. L.; El-Yazal, J.; Francois, J.-P. J. Phys. Chem. 1996, 100, 15358.
59. Bally, T.; Chai, S.; Neuenschwander, M.; Zhu, Z. J. Am. Chem. Soc. 1997, 119, 1869.
60. Le Goff, E. J. Am. Chem. Soc. 1962, 84, 3935.
61. Zyweitz, T. K.; Jiao, H.; Schleyer, P. v. R.; Meijere, A. de J. Org. Chem. 1998, 63, 3417.
62. nd Ed.; Lide, D. R., Ed.; CRC Press: Boca Raton, Florida, 2001-2002.
63. Scott, A. P.; Agranat, I.; Biedermann, P. U.; Riggs, N. V.; Radom, L. J. Org. Chem. 1997, 62, 2026.
64. Tewari, V. P.; Srivastavs, A. K. Ind. J. Chem. 1988, 27A, 657.