Copolymers of Thiophene and Thiazole. Regioregulation in Synthesis, Stacking Structure, and Optical Properties

Macromolecules

Volumn 36, Issue 21, 2003, Pages 7986-7993

  Yamamoto, Takakazu ^a   Arai, Minoru ^a   Kokubo, Hisashi ^a   Sasaki, Shintaro ^b  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b JAPAN ADVANCED INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE TRANSFER; DOPING (ADDITIVES); ELECTROCHEMISTRY; OXIDATION; POLYCONDENSATION; REDUCTION; SYNTHESIS (CHEMICAL);

STACKED STRUCTURE;

COPOLYMERS;

EID: 0142184933     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma030167n     Document Type: Article

References (69)

1. (a) McCullough, R. D.; Lowe, R. D. J. Chem. Soc., Chem. Commun. 1992, 70.
2. (b) McCullough, R. D.; Tristram-Nagle, S.; Williams, S. F.; Lowe, R. D.; Jayaraman, M. J. Am. Chem. Soc. 1993, 115, 4910.
3. (c) McCullough, R. D.; Lowe, R. D.; Jayaraman, M.; Anderson, D. L. J. Org. Chem. 1993, 58, 904.
4. (d) McCullough, R. D.; Ewband, P. C.; Loewe, R. S. J. Am. Chem. Soc. 1997, 119, 633.
5. (e) McCullough, R. D. Adv. Mater. 1998, 10, 93.
6. (a) Chen, T.-A.; Rieke, R. D. J. Am. Chem. Soc. 1992, 114, 10087.
7. (b) Chen, T.-A.; Rieke, R. D. Synth. Met. 1998, 60, 175.
8. (c) Wu, X.; Chen, T.-A.; Rieke, R. D. Macromolecules 1995, 28, 2101.
9. (d) Chen, T.-A.; Wu, X.; Rieke, R. D. J. Am. Chem. Soc. 1995, 117, 233.
10. (a) Miller, L. L.; Mann, K. R. Acc. Chem. Res. 1998, 29, 417.
11. Graf, D. D.; Duan, R. G.; Campbell, J. P.; Miller, L. L.; Mann, K. R. J. Am. Chem. Soc. 1997, 119, 5888.
12. (a) Märdalen, J.; Samuelsen, B.; Gautun, O. R.; Carlsen, P. H. Solid State Commun. 1991, 80, 687.
13. (b) Winokur, M. J.; Wamsley, P.; Moulton, J.; Smith, P.; Heeger, A. J. Macromolecules 1991, 24, 3812.
14. (c) Watanabe, J.; Harkness, B. R.; Sone, M.; Ichimura, H. Macromolecules 1994, 27, 507.
15. (a) Yamamoto, T. Chem. Lett. 1996, 703.
16. (b) Yamamoto, T.; Komarudin, D.; Arai, M.; Lee, B.-L.; Suganuma, H.; Asakawa, N.; Inoue, Y.; Kubota, K.; Sasaki, S.; Fukuda, T.; Matsuda, H. J. Am. Chem. Soc. 1998, 120, 2047.
17. (c) Yamamoto, T.; Suganuma, H.; Maruyama, T.; Inoue, T.; Muramatsu, Y.; Arai, M.; Komarudin, D.; Ooba, N.; Tomaru, S.; Sasaki, S.; Kubota, K. Chem. Mater. 1997, 9, 1217.
18. (d) Yamamoto, T.; Lee, B.-L.; Suganuma, H.; Sasaki, S. Polym. J. 1998, 30, 853.
19. (e) Yamamoto, T.; Suganuma, H.; Maruyama, T.; Kubota, K. J. Chem. Soc., Chem. Commun. 1995, 1613.
20. (F) Yamamoto, T.; Kokubo, H. J. Polym. Sci., Part B: Polym. Phys. 2000, 38, 84.
21. (g) Yamamoto, T.; Oguro, D. Macromolecules 1996, 29, 1833.
22. (a) Yamamoto, T.; Kokubo, H.; Morikita, T. J. Polym. Sci., Part B: Polym. Phys. 2001, 39, 1713.
23. (b) Morikita, T.; Yamaguchi, I.; Yamamoto, T. Adv. Mater. 2001, 13, 1862.
24. (c) Yamamoto, T.; Shiraishi, K.; Mahmut, A.; Yamaguchi, I.; Groenendaol, L. B. Polymer 2002, 711.
25. (d) Yamamoto, T.; Lee, B.-L. Macromolecules 2002, 35, 2993.
26. (a) Nanos, J. I.; Kampf, J. W.; Curtis, M. D.; Gonzalez, L.; Martin, D. C. Chem. Mater. 1995, 7, 2332.
27. (b) Politis, J. K.; Nemes, J. C.; Curtis, M. D. J. Am. Chem. Soc. 2001, 123, 2537.
28. (a) Bangcuyo, C. G.; Evans, U.; Myrick, M. L.; Bunz, U. H. F. Macromolecules 2001, 34, 7592.
29. (b) Perahia, D.; Traiphol, R.; Bunz, U. H. F. J. Chem. Phys. 2002, 117, 1827.
30. Bunz, U. H. F.; Enkelmann, V.; Kloppenburg, L.; Jones, D.; Shimizu, K. D.; Claridge, J. B.; zur Loye, H.-C.; Lieser, G. Chem. Mater. 1999, 11, 1416.
31. (a) Sirringhaus, H.; Brown, P. J.; Friend, R. H.; Nielsen, M. M.; Bechgaard, K.; Langeveld-Boss, B. M. W.; Spiering, J. H.; Janssen, R. A. J.; Meijer, E. W.; Herwig, P.; de Leeuw, D. M. Nature 1999, 401, 685.
32. (b) Sherf, U.; List, E. J. W. Adv. Mater. 2002, 14, 477.
33. n -) (refs 6a,b and 8) can form the stacked structure.
34. (a) Zhou, Z.-H.; Maruyama, T.; Kanbara, T.; Ikeda, T.; Ichimura, K.; Yamamoto, T.; Tokuda, K. J. Chem. Soc., Chem. Commun. 1991, 1210.
35. (b) Yamamoto, T.; Zhou, Z.-H.; Kanbara, T.; Shimura, M.; Kizu, K.; Maruyama, T.; Nakamura, Y.; Fukuda, T.; Lee, B.-L.; Ooba, N.; Tomaru, S.; Kurihara, T.; Kaino, T.; Kubota, K.; Sasaki, S. J. Am. Chem. Soc. 1996, 118, 10389.
36. (c) Lee, B.-L.; Yamamoto, T. Macromolecules, 1999, 32, 1375.
37. (a) Ferraris, J. P.; Bravo, A.; Kim, W.; Hrnir, D. C. J. Chem. Soc., Chem. Commun. 1994, 991.
38. (b) Karikomi, M.; Kitamura, C.; Tanaka, S.; Yamashita, Y. J. Am. Chem. Soc. 1995, 117, 6791.
39. (a) Zhu, S. S.; Swager, T. M. Adv. Mater. 1996, 8, 497.
40. (b) van Mullekom, H. A. M.; Vekemans, J. A. J. M.; Meijer, E. W. Chem. Commun. 1996, 2163.
41. (a) Zhang, Q. T.; Tour, J. M. J. Am. Chem. Soc. 1997, 119, 5065.
42. (b) Zhang, Q. T.; Tour, J. M. J. Am. Chem. Soc. 1998, 120, 5355.
43. (a) Havinga, E. E.; Ten Hoeve, W.; Wynberg, H. Polym. Bull. (Berlin) 1992, 29, 119.
44. (b) Eldo, J.; Ajayaghosh, A. Chem. Mater. 2002, 14, 410.
45. Doyle, M. P.; Siegfried, B.; Dellaria, J. F., Jr. J. Org. Chem. 1977, 42, 2425.
46. Coulson, D. Inorg. Synth. 1972, 13, 121.
47. w that are lower than the real values.
48. (a) Aizawa, M.; Watanabe, S.; Shinohara, H.; Shirakawa, H. Denki Kagaku 1984, 52, 81.
49. (b) Yamamoto, T.; Sanechika, K.; Yamamoto, A. J. Polym. Sci., Polym. Lett. Ed. 1980, 18, 9.
50. (c) Kobayashi, M.; Chen, J.; Chung, T.-C.; Moraes, F.; Heeger, A. J.; Wudl, F. Synth. Met. 1984, 9, 77.
51. (d) Yamamoto, T.; Kanbara, T.; Mori, C.; Wakayama, H.; Fukuda, T.; Inoue, T.; Sasaki, S. J. Phys. Chem. 1996, 100, 12631.
52. (a) Lére-Porte, J.-P.; Moreau, J. J.; Torreillers, C. Eur. J. Org. Chem. 2001, 1249.
53. (b) Yamamoto, T.; Honda, Y.; Kokubo, H. Polymer, submitted.
54. Marsella, M. J.; Fu, D.-K.; Swager, T. M. Adv. Mater. 1995, 7, 145.
55. (a) Andersson, M. R.; Seise, D.; Berggren, M.; Járvinen, H.; Hjerberg, T.; Inganäs, O.; Wennerström, O.; Osterholm, J. E. Macromolecules 1994, 27, 6503.
56. (b) Amou, S.; Hoba, O.; Shirato, K.; Hayakawa, T.; Ueda, M.; Takeuchi, K.; Asai, M. J. Polym. Sci., Part A: Polym. Chem. 1999, 37, 1943.
57. Soga, K; Ohgisawa, M.; Shiono, T. Makromol. Chem. Rapid Commun. 1989, 10, 503.
58. (a) Jordan, E. F., Jr.; Feideisen, D. W.; Wrigley, A. N. J. Polym. Sci., Part A-1 1971, 9, 1835.
59. (b) Hsieh, H. W.; Post, B.; Morawetz, H. J. Polym. Sci., Polym. Phys. Ed. 1976, 14, 1241.
60. (c) Swan, P. R. J. Polym. Sci. 1962, 56, 403.
61. (a) Yamamoto, T. Macromol. Rapid Commun. 2002, 23, 583.
62. (b) Yamamoto, T. Synlett 2003, 425.
63. Piesczek, Y.; Strobl, G. R.; Malzahn, K. Acta Crystallogr. 1974, B30, 1278.
64. (a) Handbook of Organic Conductive Molecules and Polymers; Nalwa, H. S., Ed.; John Wiley: Chichester, 1997.
65. (b) Yamamoto, T.; Lee, B.-L. Macromolecules 2002, 35, 2993.
66. (a) Inganäs, O.; Salaneck, W. R.; Österholm, J.-E.; Laakso, J. Synth. Met. 1988, 22, 395.
67. (b) Sandstedt, C. A.; Rieke, R. D.; Eckhardt, C. J. Chem. Mater. 1995, 7, 1057.
68. (c) Faid, K.; Frechette, M.; Ranger, M.; Mazerolle, L.; Levesgue, I.; Leclerc, M.; Chen, T. A.; Rieke, R. D. Chem. Mater. 1995, 7, 1390.
69. (d) Kokubo, H.; Yamamoto, T. Macromol. Chem. Phys. 2001, 202, 1031.