Synthesis and electrolytic polymerization of the ethylenedioxy-substituted terthiophene-fullerene dyad

Organic Letters

Volumn 6, Issue 26, 2004, Pages 4865-4868

  Yamazaki, Tetsuya ^a   Murata, Yasujiro ^a   Komatsu, Koichi ^a   Furukawa, Kazuaki ^b   Morita, Masao ^b   Maruyama, Norihiko ^a   Yamao, Takeshi ^a   Fujita, Shizuo ^a  

^a KYOTO UNIVERSITY   (Japan)

^b Kashino Diverse Brain Research Laboratory of NTT Communication Science Laboratories   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FULLERENE;

ARTICLE; ELECTROCHEMISTRY; ELECTROLYSIS; OXIDATION; POLYMERIZATION; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 12344260579     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048081h     Document Type: Article

References (37)

1. Martín, N.; Sánchez, L.; Illescas, B.; Pérez, L. Chem. Rev. 1998, 98, 2527 and references therein.
2. Diederich, F.; Gómez-López, M. Chem. Soc. Rev. 1999, 28, 263 and references therein.
3. For example, see: Brabec, C. J.; Sariciftci, N. S.; Hummelen, J. C. Adv. Funct. Mater. 2001, 11, 15.
4. Cravino, A.; Sariciftci, N. S. J. Mater. Chem. 2002, 12, 1931.
5. (a) Benincori, T.; Brenna, E.; Sannicoló, F.; Trimarco, L.; Zotti, G.; Sozzani, P. Angew. Chem., Int. Ed. Engl. 1996, 35, 648.
6. (b) Yassar, A.; Hmyene, M.; Loveday, D. C.; Ferraris, J. P. Synth. Met. 1997, 84, 231.
7. (c) Cravino, A.; Zerza, G.; Maggini, M.; Bucella, S.; Svensson, M.; Andersson, M. R.; Neugebauer, H.; Sariciftci, N. S. Chem. Commun. 2000, 2487.
8. (d) Jousselme, B.; Blanchard, P.; Levillain, E.; Bettignies, R.; Roncali, J. Macromolecules 2003, 36, 3020.
9. Murata, Y.; Suzuki, M.; Komatsu, K. Org. Biomol. Chem. 2003, 1, 2624.
10. (a) Negishi, N.; Yamada, K.; Takimiya, K.; Aso, Y.; Otsubo, T.; Harima, Y. Chem. Lett. 2003, 32, 404.
11. (b) Negishi, N.; Takimiya, K.; Otsubo, T.; Harima, Y.; Aso, Y. Chem. Lett. 2004, 33, 654.
12. Groenendaal, L. B.; Jonas, F.; Freitag, D.; Pielartzek, H.; Reynolds, J. R. Adv. Mater. 2000, 12, 481.
13. Akoudad, S.; Frére, P.; Mercier, N.; Roncali, J. J. Org. Chem. 1999, 64, 4267.
14. (a) Fu, Y.; Cheng, H.; Elsenbaumer, R. L. Chem. Mater. 1997, 9, 1720.
15. (b) Sotzig, G. A.; Thomas, T. A.; Reynolds, J. R.; Steel, P. J. Macromolecules 1998, 31, 3750.
16. (c) Akoudad, S.; Roncali, J. Chem. Commun. 1998, 2081.
17. (d) Huchet, L.; Akoudad, S.; Levillain, E.; Emge, A.; Bäuerle, P.; Roncali, J. J. Phys. Chem. 1998, 102, 7776. Akoudad, S.; Frére, P.; Mercier, N.; Roncali, J. J. Org. Chem. 1999, 64, 4267.
18. (d) Huchet, L.; Akoudad, S.; Levillain, E.; Emge, A.; Bäuerle, P.; Roncali, J. J. Phys. Chem. 1998, 102, 7776. Akoudad, S.; Frére, P.; Mercier, N.; Roncali, J. J. Org. Chem. 1999, 64, 4267.
19. (a) Sotzig, G. A.; Reynolds, J. R.; Steel, P. J. Chem. Mater. 1996, 8, 882.
20. (b) Balasubramanian, S.; Reynolds, J. R. Macromolecules 1997, 30, 2582.
21. (c) Irvin, D. J.; Dubois, C. J.; Reynolds, J. R. Chem. Commun. 1999, 2121.
22. (d) Akoudad, S.; Roncali, J. Synth. Met. 1999, 101, 149.
23. (e) Wang, F.; Wilson, M. S.; Rauh, R. D.; Schottland, P.; Thompson, B. C.; Reynolds, J. R. Macromolecules 2000, 33, 2083.
24. (f) Sonmez, G.; Meng, H.; Zhang, Q.; Wudl, F. Adv. Funct. Mater. 2003, 13, 726.
25. (a) Komatsu, K.; Murata, Y.; Takimoto, N.; Mori, S.; Sugita, N.; Wan, T. S. M. J. Org. Chem. 1994, 59, 6101.
26. (b) Anderson, H. L.; Faust, R.; Rubin, Y.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 1366.
27. (c) Tiimmerman, P.; Anderson, H. L.; Faust, R.; Nierengarten, J. L.; Habicher, T.; Seiler, P.; Diederich, F. Tetrahedron 1996, 52, 4925.
28. (d) Murata, Y.; Motoyama, K.; Komatsu, K.; Wan, T. S. M. Tetrahedron 1996, 52, 5077.
29. (e) Komatsu, K.; Takimoto, N.; Murata, Y.; Wan, T. S. M.; Wong, T. Tetrahedron Lett. 1996, 37, 6153.
30. (a) Pepitone, M. F.; Hardaker, S. S.; Gregory, R. V. Chem. Mater. 2003, 15, 557.
31. (b) Pepitone, M. F.; Eaiprasertsak, K.; Hardaker, S. S.; Gregory, R. V. Org. Lett. 2003, 5, 3229.
32. (a) Apperloo, J.; Groenendaal, L.; Verheyen, H.; Jayakannan, M.; Janssen, R. A.; Dkhissi, A.; Beljonne, D.; Lazzaroni, R.; Bredas, J. L. Chem. Eur. J. 2002, 8, 2384.
33. (b) Turbiez, M.; Frére, P.; Roncali, J. J. Org. Chem. 2003, 68, 5357.
34. Miyazaki, Y.; Kanbara, T.; Osakada, K.; Yamamoto, T. Chem. Lett. 1993, 415.
35. Deronzier, A.; Moutet, J.-C. J. Am. Chem. Soc. 1994, 116, 5019.
36. Hatano, T.; Takeuchi, M.; Ikeda, A.; Shinkai, S. Chem. Commun. 2003, 342.
37. Lahav, M.; Heleg-Shabtai, V.; Wasserman, J.; Katz, E.; Willner, I.; Durr, H.; Hu, Y.-Z.; Bossmann, S. H., J. Am. Chem. Soc. 2000, 122, 11480.