Reactions between 1-ethynylazulenes and 7,7,8,8-tetracyanoquinodimethane (TCNQ): Preparation, properties, and redox behavior of novel azulene-substituted redox-active chromophores

European Journal of Organic Chemistry

Volumn , Issue 25, 2009, Pages 4316-4324

  Shoji, Taku ^a   Ito, Shunji ^b   Toyota, Kozo ^a   Iwamoto, Takeaki ^a   Yasunami, Masafumi ^c   Morita, Noboru ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b HIROSAKI UNIVERSITY   (Japan)

^c NIHON UNIVERSITY   (Japan)

Author keywords

Azulenes; Cycloaddition; Donor acceptor systems; Electrochromism; Redox chemistry

Indexed keywords

EID: 68949086198     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900539     Document Type: Article

References (24)

1. a) J. Ferraris, D. O. Cowan, V. Walatka Jr., J. H. Perlstein, J. Am. Chem. Soc. 1973, 95, 948-949;
2. b) E. B. Vickers, T. D. Selby, M. S. Thorum, M. L. Taliaferro, J. S. Miller, Inorg. Chem. 2004, 43, 6414-6420;
3. c) E. B. Vickers, I. D. Giles, J. S. Miller, Chem. Mater. 2005, 17, 1667-1672.
4. a) M. Kivala, C. Boudon, J. Gisselbrecht, P. Seiler, M. Gross, F. Diederich, Chem. Commun. 2007, 4731-4733;
5. b) P. Reutenauer, M. Kivala, P. D. Jarowski, C. Boudon, J. P. Gisselbrecht, M. Gross, F. Diederich, Chem. Commun. 2007, 4898-4900;
6. c) M. Kivala, C. Boudon, J. Gisselbrecht, B. Enko, P. Seiler, I.-B. Müller, N. Langer, P.-D. Jarowski, G. Gescheidt, F. Diederich, Chem. Eur. J. 2009, 15, 4111-4123.
7. a) D. S. Acker, W. R. Hertler, J. Am. Chem. Soc. 1962, 84, 3370-3374;
8. b) L. R. Melby, R. J. Harder, W. R. Hertler, W. Mahler, R. E. Benson, W. E. Mochel, J. Am. Chem. Soc. 1962, 84, 3374-3387;
9. c) W. R. Hertler, H. D. Hartzler, D. S. Acker, R. E. Benson, J. Am. Chem. Soc. 1962, 84, 3387-3393;
10. d) J. K. Williams, J. Am. Chem. Soc. 1962, 84, 3478-3479;
11. e) J. Ferraris, D. O. Cowan, V. Walatka Jr., J. H. Perlstein, J. Am. Chem. Soc. 1973, 95, 948-949;
12. f) N. Martin, J. L. Segura, C. Seoane, J. Mater. Chem. 1997, 7, 1661-1676;
13. g) E. B. Vickers, T. D. Selby, M. S. Thorum, M. L. Taliaferro, J. S. Miller, Inorg. Chem. 2004, 43, 6414-6420;
14. h) E. B. Vickers, I. D. Giles, J. S. Miller, Chem. Mater. 2005, 17, 1667-1672;
15. i) K. Walzer, B. Maennig, M. Pfeiffer, K. Leo, Chem. Rev. 2007, 107, 1233-1271.
16. K.-P. Zeller, Azulene. In Houben-Weyl, Methoden der Organischen Chemie, 4th ed. (Ed.: H. Kropf), Georg Thieme, Stuttgart, Germany, 1985, vol. V, part 2c, pp. 127-418.
17. T. Shoji, S. Ito, K. Toyota, M. Yasunami, N. Morita, Chem. Eur. J. 2008, 14, 8398-8408.
18. M. Kivala, C. Boudon, J. Gisselbrecht, P. Seiler, M. Gross, F. Diederich, Angew. Chem. 2007, 119, 6473-6477;
19. Angew. Chem. Int. Ed. 2007, 46, 6357-6360.
20. Reactions between electron-rich acetylene derivatives and TCNE have recently been reported; a) T. Michinobu, J. C. May, J. H. Lim, C. Boudon, J.-P. Gisselbrecht, P. Seiler, M. Gross, I. Biaggio, F. Diederich, Chem. Commun. 2005, 737-739;
21. b) T. Michinobu, C. Boudon, J. Gisselbrecht, P. Seiler, B. Frank, N. N. P. Moonen, M. Gross, F. Diederich, Chem. Eur. J. 2006, 12, 1889-1905;
22. c) M. Kivala, T. Stanoeva, T. Michinobu, B. Frank, G. Gescheidt, F. Diederich, Chem. Eur. J. 2008, 14, 7638-7647;
23. d) J.-L. Alonso-Gómez, P. Schanen, P. Rivera-Fuentes, P. Seiler, F. Diederich, Chem. Eur. J. 2008, 14, 10564-10568;
24. e) M. Kivala, F. Diederich, Acc. Chem. Res. 2009, 42, 235-248.