Orientation-dependent electron transfer processes in fullerene-aniline dyads

Journal of Physical Chemistry A

Volumn 103, Issue 50, 1999, Pages 10755-10763

  Thomas, K George ^a,b   Biju, V ^a   Guldi, D M ^b   Kamat, Prashant V ^b   George, M V ^a,b,c  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

^b UNIVERSITY OF NOTRE DAME   (United States)

^c JAWAHARLAL NEHRU CENTRE FOR ADVANCED SCIENTIFIC RESEARCH   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0033576844     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp992369k     Document Type: Article

References (51)

1. (a) Deisenhofor, J.; Michel, H.;Angew Cliem. Int. Ed. Engl. 1989, 28, 829.
2. (b) Huber, R.; Angew. Cliem., Int. Ed. Engl 1989, 28, 848.
3. Balzani, V.; Maggi, L.; Scandola, F. In Supramolecular Photochemistry, Balzani, V., Ed.; Reidel: Holland, 1987; pp 1-28.
4. (a) Imahori, H.; Sakata, Y.; Adv. Mater. 1997, 9, 537.
5. (b) Martin, N.; Sanchez, B.; Illescas, B.; Ferez, I. Chem. Rev. 1998, 98, 2527.
6. Sun, Y.-P. In Molecular and Supramolecular Photochemistry, Vol. I, Organic Photochemistry; Ramamurthy, V., Schanze, K. S., Eds.; Marcel Dekker: New York, 1997; pp 325-390.
7. Foote, C. S. In Topics in Current Chemistry; Electron Transfer 1; Matty, J., Ed.; Springer-Verlag: Berlin, 1994; p 347.
8. (e) Kamat, P. V.; Asmus, K.-D. Interface 1996, 5, 22.
9. (f) Zhou, F.; Jehoulelt, C.; Bard, A. J. J. Am. Cliem. Soc. 1992, 114, 11004.
10. (g) Dubois, D. K.; Kadish, K. M.; Flanagan, S.; Haufler, R. E.; Chibante, L. P. E. Wilsson, L. F. J. Am. Cliem. Soc. 1992, 114, 3978.
11. (h) Arbogast, J. W.; Foote, C. S.; Kao, M. J. Am. Cliem. Soc. 1992, 114, 2277.
12. (a) Williams, R. M.; Koeberg, M.; Lawson, J. M.; An, Y.-Z. Rubin, Y.; Paddon-Row, M. N.; Verhoeven, J. W. J. Org. Cliem. 1996, 61, 5055.
13. (b) Williams, R. M.; Zwier, J. M.; Verhoeven, J. W. J. Am. Cliem. Soc. 1995, 117, 4093
14. (a) Kuciauskas, D.; Linddell, P. A.; Moore, A. L.; Moore, T. A.; Gust, D. J. Am. Cliem. Soc. 1998, 720, 10880.
15. (b) Liddell, P. A.; Kuciauskas, D.; Sumida, J. P.; Nash, B.; Nguyen, D.; Moore, A. L.; Moore, T. A.; Gust, D. J. Am. Chem. Soc. 1997,119, 1400.
16. Kuciauskas, D.; Lin, S.; Seely, G. R.; Moore, A. L.; Moore, T. A.; Gust, D.; Drovetskaya, T.; Reed, C. A.; Boyd, P. D. W. J. Phys. Chem. 1996, 100, 15926.
17. Liddell, P. A.; Sumida, J. P.; Macpherson, A. N.; Noss, L.; Seely, G. R.; Clark, K. N.; Moore, A. L.; Moore, T. A.; Gust, D. Photochem. Photobiol. 1994, 60, 537.
18. (e) Imahori, H.; Hagivvara, K.; Asoki, M.; Akiyama, T.; Taniguchi, S. Okada, T.; Shirakawa, M.; Sakata, Y. J. Am. Chem. Soc. 1996,118, 11771.
19. (f) Imahori, H.; Yamada, K.; Hasegawa, M.; Taniguchi, S. Okada, T.; Sakata, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 2626.
20. Baran, P. S.; Monaco, R. R.; Khan, A. U.; Schuster, D. I.; Wilson, S. R. J. Am. Chem. Soc. 1997, 119, 8363.
21. (a) Guldi, D. M.; Maggini, M.; Scarrano, G.; Prato, M. J. Am. Chem. Soc. 1997, 119, 974.
22. (b) Sariciftci, N. S.; Wudl, F.; Heeger, A. J.; Maggini, M.; Scarrano, G.; Prato, M.; Bourassa, J.; Ford, F. C. Chem. Phys. Lett. 1995, 247, 510.
23. (a) Thomas, K. G.; Biju, V.; George, M. V.; Guldi, D. M.; Kamat, P. V. J. Phys. Chem. 1998, 702,5341.
24. (b) Thomas, K. G.; Biju, V.; George, M. V.; Guldi, D. M.; Kamat, P. V. J. Phys. Chem. B 1999, 103, 8864.
25. (a) Connolly, J. S.; Bolton, J. R. In Photoinduced Electron Transfer, Part D; Fox, M. A., Channon, M., Eds.; Elsevier: Amsterdam, 1988; pp 303-393.
26. (b) Wasielewski, M. R. In Photoinduced Electron Transfer, Pan A; Fox, M. A., Channon, M., Eds.; Elsevier: Amsterdam, 1988; pp 161-206.
27. Osuka, A.; Morikawa, S.; Maruyama, K.; Hirayama, S.; Minami T. J. Chem. Soc., Chem. Commun. 1987, 359. (d) Fox, M. A. In Photoinduced Electron Transfer III, Topics in Current Chemistry-159; Mattay, J., Ed.; Springer- Verlag: Berlin, 1991; pp 67-101.
28. (e) Gust, D.; Moore, T. A. In Photoinduced Electron Transfer III, Topics in Current Chemistry-159; Mattay, J., Ed.; Springer- Verlag: Berlin, 1991; pp 103-151.
29. (a) Luo C.; Fujitsuka, M.; Huang, C.-H.; Ito, O. J. Phys. Chem. A. 1998, 102, 8716.
30. (11) Confirmed on a Cosmosil Buckprep HLPC column.
31. (a) For synthesis of 5, see: Maggini, G.; Scarrano, G. Prato, M. J. Am. Chem. Soc. 1993, 115, 9798.
32. (b) For the preparation of 10 through a different route see, Liang, K.; Law, K.-Y.; Whitten, D. G. J. Phys. Chem. B 1997, 101, 540.
33. Nagarajan, V.; Fessenden, F. W. J. Phys. Chem. 1985, 89, 2330.
34. Evaluated using the Sybyl force field method of PC SPARTAN software obtained from Wavefunction, Inc.; 18401, Von Kaiman, Suite 370, Irvine, CA 92612.
35. (a) For discussions on the 700 nm band observed in the case of methanofullerene derivatives see, Bensasson, R. V.; Bienvenue, E.; Fahre, C. Janot, J.-M.; Land, E. J.; Leach, S.; Leboulaire, V.; Rassat, A.; Roux, S.; Seta, P. Chem. Eur. J. 1998, 4, 270.
36. (b) Guldi, D. M.; Maggini M. Gazz. Chim. Ital. 1997, 727, 779.
37. Prato, M.; Maggini, M.; Ace. Chem. Res. 1998, 31, 519.
38. Protonation of the anilinic nitrogen by adding trifluoroacetic acid (25 mM) to ClhCh solutions of dyads 2-4 causes a partial disappearance of the band around 700 nm. This change is completely reversed by adding pyridine (30 mM) to the above solution. The absorption spectrum of the model compound was found to be unaffected by the addition of TFA (250 mM), ruling out the possibility of a ground state charge transfer interaction.
39. (a) Sun, Y.-P.; Ma, B.; Lawson, G. E. Chem. Phys. Lett. 1995, 233, 57.
40. (b) Sun, Y.-P.; Bunker, C. E.; Ma, B. J. Am. Chem. Soc. 1994, 116,9692.
41. Seshadri, R.; Rao, C. N. R.; Pal, H.; Mukherjee, T.; Mitttal, J. P. Chem. Phys. Lett. 1993, 205, 395.
42. Wang, Y. J. Phys. Chem. 1992, 96,764.
43. (e) Nakamura, Y.; Minowa, T.; Hayashida, Y.; Tobita, S.; Shizuka, H.; Nishimura, J. J. Chem. Soc., Faraday Trans. 1996, 92, 377.
44. 4,7a
45. An increase in fluorescence was observed on addition of trifluoroacetic acid (25 mM) to benzonitrile solution of dyads 1-4 (~80% of 0f of that in toluene) and is due to the protonation of the anilinic nitrogen which inhibits the electron transfer processes.
46. ref = 1280 ps];
47. cs].
48. (a) Sakata, Y.; Nakashima, S.; Goto, Y.; Misumi, S.; Asahi, T.; Hagihara, M.; Nishikawa, S.; Okada, T.; Malaga, N. J. Am. Client. Soc. 1989, 111, 8979.
49. (b) Wasielewski, M. R.; Niemczyk, M. P.; Johnson, D. G.; Svec, W. A.; Minsek, D. W. Tetrahedron 1989, 45, 4785.
50. Sakata, Y.; Tsue, H.; Goto, Y.; Misumi, S.; Asahi, T.; Nishikawa, S.; Okada, T.; Malaga, N. Chem. Lett. 1991, 1307.
51. Luo, C.; Fujitsuka, M.; Watanabe, A.; Ito, O.; Can, L.; Huang, Y.; Huang, C.-H. J. Chem. Soc., Faraday Trails. 1998, 94, 527.