Synthesis of n-type poly(benzotriazole)s having p-conducting and polymerizable carbazole pendants

Macromolecules

Volumn 39, Issue 10, 2006, Pages 3546-3552

  Tanimoto, Akitoshi ^a   Yamamoto, Takakazu ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COPOLYMERIZATION; DOPING (ADDITIVES); ELECTROCHEMISTRY; MOLECULAR WEIGHT; ORGANOMETALLICS; PALLADIUM; PHOTOLUMINESCENCE; POLYCONDENSATION; SYNTHESIS (CHEMICAL);

HOMOPOLYMERS; P-PHENYLENE; POLY BENZOTRIAZOLES P(BTZ); QUANTUM YIELDS;

ORGANIC POLYMERS;

EID: 33744466349     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma052688b     Document Type: Article

References (56)

1. (a) Handbook of Conducting Polymers, 2nd ed.; Stokheim, T. A., Elsenbaumer, R. L., Reinolds, J. R., Eds.; Dekker: New York, 1997.
2. (b) McCullough, R. D. Handbook of Oligo- and polythiophene; Ficher, D., Ed.; Wiley-VCH: Weinheim, Germany, 1999.
3. (c) Yamamoto, T. Bull. Chem. Soc. Jpn. 1999, 72, 621.
4. (d) Handbook of Organic Conductive Molecules and Polymers; Nalwa, H. S., Ed.; Wiley: Chichester, U.K., 1997; Vol. 2.
5. (a) Heywang, G.; Jonas, F. Adv. Mater. 1992, 4, 116.
6. (b) Kudoh, Y.; Fukuyama, M.; Kojima, T.; Nanai, N.; Yoshimura, S. In Intrinsically Conducting Polymers: An Emerging Technology; Aldissi, M., Ed.; Kluwer Academic; Dordrecht, The Netherlands, 1992.
7. (c) Patil, A. O.; Ikenoue, Y.; Wudl, F.; Heeger, A. J. J. Am. Chem. Soc. 1987, 109, 1858.
8. (d) Catalogue of Achilles Corporation; 22 Daikyo-cho, Shinjuku-ku, Tokyo, Japan.
9. (a) Freudenmann, R.; Behnisch, B.; Hanack, M. J. Mater. Chem. 2001, 11, 1618.
10. (b) Thomas, K. R. J.; Velusamy, M.; Lin, J. T.; Tao, Y.-T.; Chuen, C.-H. Adv. Funct. Mater. 2004, 14, 387.
11. (c) Li, Z. H.; Wong, M. S.; Fukutani, H.; Tao, Y. Chem. Mater. 2005, 17, 5032.
12. (d) Cea, P.; Hua, Y.; Pearson, C.; Wang, C.; Bryçe, M. R.; Royo, F. M.; Petty, M. C. Thin Solid Films 2002, 408, 275.
13. (e) Karabunarliev, S.; Bittner, E. R. J. Phys. Chem. B 2004, 108, 10219.
14. (f) Morteani, A. C.; Dhoot, A. S.; Kim, J.-S.; Silva, C.; Greenham, N. C.; Murphy, C.; Moons, E.; Ciná, S.; Burroughes, J. H.; Friend, R. H. Adv. Mater. 2003, 15, 1708.
15. (g) Lee, S. K.; Hwang, D.-H.; Jung, B.-J.; Cho, N. S.; Lee, J.; Lee, J.-D.; Shin, H.-K. Adv. Funct. Mater. 2005, 15, 1647.
16. (a) Babel, A.; Wind, J. D.; Jenekhe, S. A. Adv. Funct. Mater. 2004, 14, 891.
17. (b) Meijer, E. J.; deLeeuw, D. M.; Setayesh, S.; van-Veenendaal, E.; Huisman, B.-H.; Blom, P. W. M.; Hummelen, J. C.; Scherf, U.; Klapwijk, T. M. Nat. Mater. 2003, 2, 678.
18. (c) Dodabalapur, A.; Katz, H. E.; Torsi, L.; Haddon, R. C. Science 1995, 209, 1560.
19. (d) Chesterfield, R. J.; Newman, C. R.; Pappenfus, T. M.; Ewbank, P. C.; Haukaas, M. H.; Mann, K. R.; Miller, L. L.; Frisbie, C. D. Adv. Mater. 2003, 75, 1278.
20. (e) Yamamoto, T.; Yasuda, T.; Sakai, Y.; Aramaki, S. Macromol. Rapid Commun. 2005, 26, 1214.
21. (a) Chung, S.-J.; Kwon, K.-Y.; Lee, S.-W.; Jin, J.-I.; Lee, C. H.; Lee, C. E.; Park, Y. Adv. Mater. 1998, 10, 1112.
22. (b) Sung, H.-H.; Lin, H.-C. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 2700.
23. (c) Sanda, F.; Kawaguchi, T.; Masuda, T.; Kobayashi, N. Macromolecules 2003, 36, 2224.
24. (d) Lee, G. J.; Kim, K.; Jin, J.-I. Opt. Commun. 2000, 203, 151.
25. (e) An, B.-K.; Kim, Y.-H.; Shin, D.-C.; Park, S. Y.; Yu, H.-S.; Kwon, S.-K. Macromolecules 2001, 34, 3993.
26. (f) Lu, S.; Liu, T.; Ke, L.; Ma, G.-G.; Chua, S.-J.; Huang, W. Macromolecules 2005, 38, 8494.
27. (g) Liang, F.; Kurata, T.; Nishide, H.; Kido, J. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 5765.
28. (a) Meerhold, K.; Gregorius, H.; Müller, K.; Heinze, J. Adv. Mater. 1994, 6. 671.
29. (b) Yamamoto, T.; Xu, Y.; Inoue, T.; Yamaguchi, I. J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 1493.
30. (a) Yamamoto, T.; Sugiyama, K.; Kanbara, T.; Hayashi, H.; Etori, H. Macromol. Chem. Phys. 1998, 199, 1807.
31. (b) Tanimoto, A.; Shiraishi, K.; Yamamoto, T. Bull. Chem. Soc. Jpn. 2004, 77, 597.
32. (a) Kanbara, T.; Yamamoto, T. Chem. Lett. 1993, 583.
33. (b) Bernius, M. T.; Inbasekaran, M.; O'brien, J.; Wu, W. Adv. Mater. 2000, 12, 1737 and references therein.
34. (c) Tessler, N,; Medvedev, V.; Kazes, M.; Kan, S.; Banin, U. Science 2002, 295, 1506.
35. (d) Huang, J.; Xu, Y.; Hou, Q.; Yang, W.; Yuan, M.; Cao, Y. Macromol. Rapid Commun. 2002, 23, 709.
36. (e) Witker, D.; Reinolds, J. R. Macromolecules 2005, 38, 7636.
37. (f) Yamamoto, T.; Fang, Q.; Morikita, T. Macromolecules 2003, 36, 4262.
38. (a) Tanimoto, A.; Yamamoto, T. Adv. Synth. Catal. 2004, 346, 1818.
39. (b) Ahn, S.-H.; Czae, M.-Z.; Kim, E.-R.; Lee, H.; Han, S.-H.; Noh, J.; Hara, M. Macromolecules 2001, 34, 2522.
40. (a) Atta-ur-Rahman Nuclear Magnetic Resonance. Basic Principles; Springer-Verlag: New York, 1986.
41. (b) Kamiya, M.; Katayama, S.; Akahori, Y. Chem. Pharm. Bull. 1969, 17, 1821.
42. Xia, C.; Advincula, R. C. Chem. Mater. 2001, 13, 1682.
43. Melhuish, W. H. J. Phys. Chem. 1962, 65, 229.
44. (a) Diamant, Y.; Furmanovich, E.; Landau, A.; Lellouche, J.-P.; Zaban, A. Electrochim. Acta 2003, 48, 507.
45. (b) Macit, H.; Sen, S.; Sacak, M. J. Appl. Polym. Sci. 2005, 96, 894.
46. (c) Gracia-Melmonte, G.; Pomerantz, Z.; Bisquert, J.; Lellouche, J.-P.; Zaban, A. Electrochim. Acta 2004, 49, 3413.
47. (d) Sarac, A. S.; Sezer, E.; Ustamehmetoglu, B. Polym. Adv. Technol. 1997, 8, 556.
48. Yamamoto, T.; Sugiyama, K.; Kushida, T.; Inoue, T.; Kanbara, T. J. Am. Chem. Soc. 1996, 118, 3930.
49. (a) Mazik, M.; Bläser, D.; Boese, R. J. Org. Chem. 2005, 70, 9115.
50. (b) Pickering, A. L.; Seeber, G.; Long. D.-L.; Cronin, L. Cryst. Eng. Commun. 2005, 7, 504.
51. (c) Aglifoglio, G.; Karam. A. R.; Catari, E. L.; Gronzalez, T.; Atencia, R. Acta Crystallogr. Sect. E 2005, 61, o2613.
52. Jenekhe, S. A.; Lu, L.; Alam, M. M. Macromolecules, 2001, 34, 7315.
53. Grochala, W.; Hoffman, R.; Edwards, P. P. Chem. - Eur. J. 2003, 9, 575.
54. Ikeda, T.; Lee, B.; Kurihara, S.; Tazuke, S.; Ito, S.; Yamamoto, M. J. Am. Chem. Soc. 1988, 110, 8299.
55. Bogdanovi, B.; Kroener, M.; Wilke, G.; Justus, L. Ann. Chem. 1966, 699, 1.
56. Vahlenkamp, T.; Wegner, G. Macromol. Chem. Phys. 1994, 195, 1933.