Efficient charge separation in C60-based dyads: Triazolino[4',5':1,2][60]fullerenes

Journal of Organic Chemistry

Volumn 65, Issue 7, 2000, Pages 1978-1983

  Guldi, Dirk M ^a   González, Susana ^b   Martín, Nazario ^b   Antón, Aránzazu ^c   Garín, Javier ^c   Orduna, Jesús ^c  

^a UNIVERSITY OF NOTRE DAME   (United States)

^b UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^c CSIC   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

FULLERENE DERIVATIVE; TETRATHIAFULVALENE DERIVATIVE; TRIAZOLINE DERIVATIVE;

ARTICLE; ELECTRON TRANSPORT; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; PHOTODYNAMICS; QUANTUM CHEMISTRY;

EID: 0342264588     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991248d     Document Type: Article

References (39)

1. (a) Kurreck, H.; Huber, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 849.
2. (b) Wasielewski, M. R. In Photoinduced Electron Transfer; Fox, M. A., Chanon, M., Eds.; Elsevier: Amsterdam, 1988.
3. (c) Wasielewski, M. R. Chem. Rev. 1992, 92, 435.
4. (d) Gust, D.; Moore, T. A.; Moore, A. L. Acc. Chem. Res. 1993, 26, 198.
5. (e) Paddon-Row, M. N. Acc. Chem. Res. 1994, 27, 18.
6. (a) Martín, N.; Sánchez, L.; Illescas, B.; Pérez, I. Chem. Rev. 1998, 98, 2527.
7. (b) Imahori, H.; Sakata, Y. Adv. Mater. 1997, 9, 537.
8. (a) Martín, N.; Sánchez, L.; Seoane, C.; Andreu, R.; Garín, J.; Orduna, J., Tetrahedron Lett., 1996, 37, 5979.
9. (b) Martín, N.; Sánchez, L.; Herranz, M. A.; Guldi, D. M. J. Phys. Chem., in press.
10. Khodorkovsky, V.; Becker, J. Y. In Organic Conductors: Fundamentals and Applications; Farges, J.-P., Ed.: Marcel Dekker: New York, 1994; Chapter 3.
11. (a) Llacay, J.; Veciana, J.; Vidal-Gancedo, J.; Bourdelande, J. L.; González-Moreno, R.; Rovira, C. J. Org. Chem. 1998, 63, 5201.
12. (b) Merrant, M. A.; Martín, N. Org. Lett. 1999, 1, 2005.
13. Simonsen, K. C.; Konovalov, V. V.; Konovalova, T. A.; Kawai, T.; Cava, M. P.; Kispert, L. D.; Metzger, R. M.; Becher, J., J. Chem. Soc., Perkin Trans. 2 1999, 657-665.
14. Prato, M.; Li, Q. C.; Wudl, F.; Lucchini, V. J. Am. Chem. Soc. 1993, 115, 1148.
15. (a) Grösser, T.; Prato, M.; Lucchini, V.; Hirsch, A.; Wudl, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 1343.
16. (b) Schick, G.; Hirsch, A.; Mauser, H.; Clarck, T. Chem.-Eur. J. 1996, 2, 935.
17. (a) Lamparth, I.; Nuber, B.; Schick, G.; Skiebe, A.; Grösser, T.; Hirsch, A., Angew. Chem., Int. Ed. Engl. 1995, 34, 2257.
18. (b) Hummelen, J. C.; Knight, B.; Pavlovich, J.; González, R.; Wudl, F. Science 1995, 269, 1554.
19. (c) Nuber, B.; Hirsch, A. J. Chem. Soc., Chem. Commun. 1998, 1421.
20. (d) Keshavarz-K, M.; González, R.; Hicks, R.; Srdanov, G.; Srdanov, V.; Collins, T.; Hummelen, J.; Bellavia-Lund, C.; Pavlovich, J.; Wudl, F. Nature 1996, 383, 147.
21. Nuber, B.; Hampel, F.; Hirsch, A. Chem. Commun. 1996, 1799.
22. Lau, J.; Simonsen, O.; Becker, J. Synthesis 1995, 521.
23. Echegoyen, L.; Echegoyen, L. E. Acc. Chem. Res. 1998, 31, 593-601.
24. 60, linked to a ferrocene as an electron-donor moiety. However, no photophysical data were reported: Ros, T. D.; Prato, M.; Carano, M.; Ceroni, P.; Paolucci, F.; Roffia, S. J. Am. Chem. Soc. 1998, 120, 11645-11648.
25. (a) Martín, N.; Sánchez, L.; Seoane, C.; Andreu, R.; Garín, J.; Orduna, J.; Ortí, E.; Viruela, P. M.; Viruela, R. J. Phys. Chem. Solids 1997, 58, 1713.
26. (b) Prato, M.; Maggini, M. Acc. Chem. Res. 1998, 31, 519-526.
27. Sun, Y.-P. In Molecular and Supramolecular Photochemistry; Ramamurthy, V., Schanze, K., Eds.; Marcel Dekker: New York, 1997; Vol. 1, 325-390.
28. Guldi, D. M.; Asmus, K.-D. J. Phys. Chem. A 1997, 101, 1472-1481.
29. Weller, A. Z. Physik. Chem. 1982, 132, 93.
30. Foote, C. Top. Curr. Chem. 1994, 169, 347.
31. Guldi, D. M.; Maggini, M.; Scorrano, G.; Prato, M. J. Am. Chem. Soc. 1997, 119, 974.
32. 60-TTF). To probe this bimolecular reaction, the triplet quantum yield of dyad 5 and reference 6 was determined as a function of laser intensity (5.9%, 15.7%, 80%, and 100%), but no significant deviation in the triplet quantum yields were noticed, which rules out this mechanism.
33. Alam, M. M.; Watanabe, A.; Ito, O. Photochem Photobiol. 1997, 104, 59-64.
34. Guldi, D. M.; Hungerbühler, H.; Janata, E.; Asmus, K.-D. J. Chem. Soc., Chem. Commun. 1993, 84.
35. Jolliffe, K. A.; Langford, S. J.; Ranasinghe, M. G.; Shephard, M. J.; Paddon-Row, M. N. J. Org. Chem. 1999, 64, 1238.
36. Bell, T. D. M.; Smith, T. A.; Ghiggino, K. P.; Ranasinghe, M. G.; Shepard, M. J.; Paddon-Row, M. N. Chem. Phys. Lett. 1997, 268, 223.
37. (a) Lawson, J. M.; Oliver, A. M.; Rothenfluh, D. F.; An, Y.-A.; Ellis, G. A.; Ranasinghe, M. G.; Khan, S. L; Franz, A. G.; Ganapathi, P. S.; Shephard, M. J.; Paddon-Row: M. N.; Rubin, Y. J. Org. Chem. 1996, 67, 5032.
38. (b) Williams, R. M.; Koeberg, M.; Lawson, J. M.; An, Y.-Z.; Rubin, Y.; Paddon-Row: M. N.; Verhoeven, J. W. J. Org. Chem., 1996, 61, 5055.
39. Thomas, M. D.; Hug, G. L. Comput. Chem. 1998, 22, 491.