Synthesis and characterization of p-phenylenediamine derivatives bearing an electron-acceptor unit

Journal of Organic Chemistry

Volumn 70, Issue 7, 2005, Pages 2754-2762

  Sakurai, Hidehiro ^a   Ritonga, Mendra T S ^a   Shibatani, Harumi ^a   Hirao, Toshikazu ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION; CATALYST ACTIVITY; CYCLIC VOLTAMMETRY; DERIVATIVES; OLIGOMERS; OXIDATION; PALLADIUM; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

BENZOTHIADIAZOLE (BT); ELECTRON ACCEPTORS; P-PHENYLENEDIAMINE; QUINOXALINE (QX);

AROMATIC COMPOUNDS;

AMINO ACID; ANILINE; BENZOTHIAZOLE DERIVATIVE; OLIGOMER; PALLADIUM; PHENYLENEDIAMINE DERIVATIVE; QUINONE DERIVATIVE; QUINOXALINE; SILVER;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; DERIVATIZATION; ELECTRON TRANSPORT; ISOMER; OLIGOMERIZATION; OXIDATION KINETICS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 17044370417     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048324j     Document Type: Article

References (57)

1. (a) Nakajima, T.; Kawagoe, T. Synth. Met. 1989, 28, C629.
2. (b) Bergeron, J.-Y.; Dao, L. H. Macromolecules 1992, 25, 3332.
3. (a) Kitani, A.; Kaya, M.; Sakaki, K. J. Electrochem. Soc. 1986, 133, 1069.
4. (b) MacDiarmid, A. G.; Yang, L. S.; Huang, W. S.; Humphrey, B. D. Synth. Met. 1987, 18, 393.
5. Gustafsson, G.; Cao, Y.; Treacy, G. M.; Klavetter, F.; Colaneri, N.; Heeger, A. G. Nature 1992, 356, 47.
6. DeBerry, D. J. Electrochem. Soc. 1985, 132, 1022.
7. (a) Genies, E. M.; Lapkowski, M.; Santier, C.; Vieil, E. Synth. Met. 1987, 18, 631.
8. (b) Nguyen, M. T.; Dao, L. H. J. Electrochem. Soc. 1989, 136, 2131.
9. (c) Paul, E. W.; Ricco, A. J.; Wrighton, M. S. J. Phys. Chem. 1985, 89, 1441.
10. Nagaoka, T.; Kakuno, K.; Fujimoto, M.; Nakao, H.; Yano, J.; Ogura, K. J. Electroanal. Chem. 1994, 368, 315.
11. Noufi, R.; Nozik, A. J.; White, J.; Warren, L. F. J. Electrochem. Soc. 1982, 129, 2261.
12. Epstein, A. J.; Ginder, J. M., Ritcher, A. F.; MacDiarmid, A. G. In Conducting Polymers; Alcacer, L., Ed.; Reidel: Holland, 1987; p 121.
13. Kaplan, S.; Conwell, E. M.; Richter, A. F.; MacDiarmid, A. G. Synth. Met. 1989, 29, E235.
14. (a) Hirao, T.; Higuchi, M.; Ikeda, I.; Oshiro, Y. J. Chem. Soc., Chem. Commun. 1993, 194.
15. (b) Hirao, T.; Higuchi, M.; Oshiro, Y.; Ikeda, I. Chem. Lett. 1993, 1889.
16. (c) Higuchi, M.; Ikeda, I.; Hirao, T. J. Org. Chem. 1997, 62, 1072.
17. Hirao, T.; Fukuhara, S. J. Org. Chem. 1998, 63, 7534.
18. (a) Higuchi, M.; Yamaguchi, S.; Hirao, T. Synlett 1996, 1213.
19. (b) Higuchi, M.; Imoda, D.; Hirao, T. Macromolecules 1996, 29, 8277.
20. (c) Hirao, T.; Yamaguchi, S.; Fukuhara, S. Tetrahedron Lett. 1999, 40, 3009.
21. (d) Hirao, T.; Yamaguchi, S.; Fukuhara, S. Synth. Met. 1999, 106, 67.
22. (e) Moriuchi, T.; Bandoh, S.; Miyaishi, M.; Hirao, T. Eur. J. Inorg. Chem. 2001, 651.
23. (f) Hirao, T.; Fukuhara, S.; Otomaru, Y.; Moriuchi, T. Synth. Met. 2001, 123, 373.
24. (a) Bredas, J. L.; Heeger, A. J.; Wudl, F. J. Chem. Phys. 1986, 85, 4673.
25. (b) Bredas, J. L. Synth. Met. 1987, 17, 115.
26. Roncali, J. Chem. Rev. 1997, 97, 173.
27. (a) Havinga, E. E.; ten Hoeve, W.; Wynberg, H. Polym. Bull. 1992, 29, 119.
28. (b) Havinga, E. E.; ten Hoeve, W.; Wynberg, H. Synth. Met. 1993, 55, 299.
29. (a) Karikomi, M.; Kitamura, C.; Tanaka, S.; Yamashita, Y. J. Am. Chem. Soc. 1995, 117, 6791.
30. (b) Kitamura, C.; Tanaka, S.; Yamashita, Y. Chem. Mater. 1996, 8, 570.
31. Akoudad, S.; Roncali, J. Chem. Commun. 1998, 2081.
32. van Mullekom, H. A. M.; Vekemans, J. A. J. M.; Meijer, E. W. Chem. Commun. 1996, 2163.
33. (a) Yamashita, Y.; Ono, K.; Tomura, M.; Tanaka, S. Tetrahedron 1997, 53, 10169.
34. (b) van Mullekom, H. A. M.; Vekemans, J. A. J. M.; Meijer, E. W. Chem. Eur. J. 1998, 4, 1235.
35. (c) Raimundo, J. M.; Blanchard, P.; Brisset, H.; Akoudad, S.; Roncali, J. Chem. Commun. 2000, 939.
36. (d) Morikita, T.; Yamaguchi, I.; Yamamoto, T. Adv. Mater. 2001, 13, 1862.
37. (e) Jayakannan, M.; van Hal, P. A.; Janssen, R. A. J. J. Polym. Sci. A 2002, 40, 2360.
38. (f) Kitamura, C.; Saito, K.; Nakagawa, M.; Ouchi, M.; Yoneda, A.; Yamashita, Y. Tetrahedron Lett. 2002, 43, 3373.
39. (a) Yamamoto, T.; Maruyama, T.; Zhou, Z.-H.; Ito, T.; Fukuda, T.; Yoneda, Y.; Begum, F.; Ikeda, T.; Sasaki, S.; Takezoe, H.; Fukuda, A.; Kubota, K. J. Am. Chem. Soc. 1994, 116, 4832.
40. (b) Yamamoto, T.; Kanbara, T.; Ooba, N.; Tomaru, S. Chem. Lett. 1994, 1709.
41. (c) 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.
42. Preliminary results have been reported. See: (a) Ritonga, M. T. S.; Sakurai, H.; Hirao, T. Tetrahedron Lett. 2002, 43, 9009. (b) Hirao, T.; Sakurai, H.; Ritonga, M. T. S. Proc. Electrochem. Soc. 2003, 12, 189.
43. Preliminary results have been reported. See: (a) Ritonga, M. T. S.; Sakurai, H.; Hirao, T. Tetrahedron Lett. 2002, 43, 9009. (b) Hirao, T.; Sakurai, H.; Ritonga, M. T. S. Proc. Electrochem. Soc. 2003, 12, 189.
44. Pilgram, K.; Zupan, M.; Skiles, R. J. Heterocycl. Chem. 1970, 7, 629.
45. Sadighi, J. P.; Singer, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 4960.
46. Kranenburg, M.; van der Burgt, Y. E. M.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Goublitz, K.; Fraanje, J. Organometallics 1995, 14, 3081.
47. (a) Tsubata, Y.; Suzuki, T.; Miyashi, T.; Yamashita, Y. J. Org. Chem. 1992, 57, 6749.
48. (b) Yamamoto, T.; Sugiyama, K.; Kushida, T.; Inoue, T.; Kanbara, T. J. Am. Chem. Soc. 1996, 118, 3930.
49. Kalinowski, H.-O.; Berger, S.; Braun, S. In Carbon-13 NMR Spectroscopy; Wiley: Chichester, 1998; p 572.
50. The related paper has been reported. See: MacDiarmid, A. G.; Zhou, Y.; Feng, J. Synth. Met. 1999, 100, 131.
51. (a) Pickup, P. G. J. Mater. Chem. 1999, 9, 1641.
52. (b) Kokil, A.; Shiyanovskaya, I.; Singer, K. D.; Weder, C. J. Am. Chem. Soc. 2002, 124, 9978.
53. (c) Kokil, A.; Huber, C.; Caseri, W. R.; Weder, C. Macromol. Chem. Phys. 2003, 204, 40.
54. (d) Wang, F.; Lai, Y.-H.; Han, M. Y. Org. Lett. 2003, 5, 4791 and references therein.
55. (a) Kowalski, G.; Pielichowski, J. Synlett 2002, 2107.
56. (b) Kowalski, G.; Pielichowski, J.; Jasieniak, M. Appl. Catal., A 2003, 247, 295.
57. Albuquerque, J. E.; Mattoso, L. H. C.; Balogh, D. T.; Faria, R. M.; Masters, J. G.; MacDiarmid, A. G. Synth. Met. 2000, 113, 19.