Photophysical and Electron-Transfer Properties of Mono- and Multiple-Functionalized Fullerene Derivatives

Journal of Physical Chemistry B

Volumn 104, Issue 19, 2000, Pages 4625-4632

  Sun, Ya Ping ^a,b   Guduru, Radhakishan ^b   Lawson, Glenn E ^b   Mullins, Jason E ^b   Guo, Zhixin ^b   Quinlan, Jessica ^b   Bunker, Christopher E ^c   Gord, James R ^c  

^a CLEMSON UNIVERSITY   (United States)

^b AIR FORCE RESEARCH LABORATORY   (United States)

^c Idaho Eng/Environmental Laboratory   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001364255     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0000329     Document Type: Article

References (60)

1. (a) Foote, C. S. In Topics in Current Chemistry, Electron-Transfer I: Mattay, J., Ed.; Springer-Verlag: Berlin, 1994; p 347.
2. (b) Foote, C. S. In Light-Activated Pest Control; Heitz, J. R., Downum, K. R., Eds.; ACS Symposium Series 616; American Chemical Society: Washington, DC, 1995; p 17.
3. Sun, Y.-P. In Molecular and Supramolecular Photochemistry; Ramamurthy, V., Schanze, K. S., Eds.; Marcel Dekker: New York, 1997; Vol. 1, p 325.
4. Leach, S. In Physics and Chemistry of the Fullerenes; Prassides, K., Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1994; p 117.
5. Jensen, A. W.; Wilson, S. R.; Schuster, D. I. Bioorg. Med. Chem. 1996, 4, 767.
6. Sun, Y.-P.; Riggs, J. E.; Guo, Z.; Rollins, H. W. In Optical and Electronic Properties of Fullerenes and Fullerene-Based Materials; Shinar, J., Vardeny, Z. V., Kafafi, Z. H., Eds.; Marcel Dekker: New York, 1999; p 43.
7. Tutt, L. W.; Kost, A. Nature 1992, 356, 225.
8. McLean, D. G.; Sutherland, R. L.; Brant, M. C.; Brandelik, D. M. Opt. Lett. 1993, 18, 858.
9. (a) Riggs, J. E.; Sun, Y.-P. J. Phys. Chem. A 1999, 103, 485.
10. (b) Riggs, J. E.; Sun, Y.-P. J. Chem. Phys. 2000, in press.
11. Sun, Y.-P.; Riggs. J. E. Int. Rev. Phys. Chem. 1999, 18, 43.
12. (a) Gust, D.; Moore, T. A.; Moore. A. L. Res. Chem. Intermed. 1997, 23, 621.
13. (b) Imahori, H.; Sakata, Y. Adv. Mater. 1997, 9, 537.
14. (c) Williams, R. M.; Koeberg, M.; Lawson, J. M.; An. Y.-Z.; Rubin, Y.; Paddon-Row, M.; Verhoeven, J. W. J. Org. Chem. 1996, 61, 5055.
15. (d) Guldi. D. M.; Maggini, M.; Scorrano, G.; Prato, M. J. Am. Chem. Soc. 1997, 119, 974.
16. (e) Carbonera, D.; Valentin, M. D.; Corvaja, C.; Agostini, G.; Giacometti, G.; Liddell, P. A.; Kuciauskas, D.; Moore, A. L.; Moore, T. A.; Gust, D. J. Am. Chem. Soc. 1998, 120, 4398.
17. (f) Baran, P. S.; Monaco, R. R.; Khan, A. U.; Schuster, D. I.; Wilson, S. R. J. Am. Chem. Soc. 1997, 119, 8363.
18. (g) Steinberg-Yfrach, G.; Rigaud, J.-L.; Durantini, E. N.; Moore, A. L.; Gust, D.; Moore, T. A. Nature 1998, 392, 479.
19. (h) Steinberg-Yfrach, G.; Liddell, P. A.; Huang, S.-C.; Moore, A. L.; Gust, D.; Moore, T. A. Nature 1997, 385, 239.
20. (a) Diederich, F.; Thilgen, C. Science 1996, 271, 317.
21. (b) Prato, M. J. Mater. Chem. 1997, 7, 1097.
22. (c) Hirsh, A. Top. Curr. Chem. 1998, 199, 1.
23. Ma, B.; Bunker, C. E.; Guduru, R.; Zhang, X.-F.; Sun, Y.-P. J. Phys. Chem. A 1997, 101, 5626.
24. Sun, Y.-P.; Lawson, G. E.; Riggs, J. E.; Ma, B.; Wang, N.; Moton, D. K. J. Phys. Chem. A 1998, 102, 5520.
25. Ma, B.; Riggs, J. E.; Sun, Y.-P. J. Phys. Chem. B 1998, 102, 5999.
26. (a) Guldi, D. M.; Asmus, K.-D. J. Phys. Chem. A 1997, 101, 1472.
27. (b) Mohan, H.; Palit, D. K.; Mittal, J. P.; Chiang, L. Y.; Asmus, K. D.; Guldi, D. M. J. Chem. Soc., Faraday Trans. 1998, 94, 359.
28. (a) Palit, D. K.; Mohan, H.; Mittal, J. P. J. Phys. Chem. A 1998, 102, 4456.
29. (b) Palit, D. K.; Mohan, H.; Birkett, P. R.; Mittal, J. P. J. Phys. Chem. A 1997, 101, 5418.
30. (c) Bensasson, R. V.; Hill, T. J.; Land, E. J.; Leach, S.; McGarvey, D. J.; Truscott, T. G.; Ebenhoch, J.; Gerst, M.; Ruchart, C. Chem. Phys. 1997, 215, 111.
31. (d) Kadish, K. M.; Gao, X.; Van, C. E.; Hirasaka, T.; Suenobu, T.; Fukuzumi, S. J. Phys. Chem. A 1998, 102, 3898.
32. (e) Fujitsuka, M.; Ito, O.; Maeda, Y.; Kako, M.; Wakahara, T.; Akasaka, T. Phys. Chem. Chem. Phys. 1999, 1, 3527.
33. (f) Coheur, P.-F.; Cornil, J.; dos Santos, D. A.; Birkett, P. R.; Liévin, J.; Brédas, J. L.; Janot, J.-M.; Seta, P.; Leach, S.; Walton, D. R. M.; Taylor, R.; Kroto, H. W.; Colin, R. Synth. Met. 1999, 103, 2407.
34. (g) Nakamura, Y.; Taki, M.; Tobita, S.; Shizuka, H.; Yokoi, H.; Ishiguro, K.; Sawaki, Y.; Nishimura, J. J. Chem. Soc., Perkin Trans. 2 1999, 127.
35. (h) Janot, J. M.; Eddaoudi, H.; Seta, P.; Ederlé, Y.; Mathis, C. Chem. Phys. Lett. 1999, 302, 103.
36. Prat, F.; Stackow, R.; Bernstein, R.; Qian, W.; Rubin, Y.; Foote, C. S. J. Phys. Chem. A 1999, 103, 7230.
37. (a) Schick, G.; Levitus, M.; Kvetko, L.; Johnson, B. A.; Lamparth, I.; Lunkwitz, R.; Ma, B.; Khan, S. I.; Garcia-Garibay, M. A.; Rubin, Y. J. Am. Chem. Soc. 1999, 121, 3246.
38. (b) Hutchison, K.; Gao, J.; Schick, G.; Rubin, Y.; Wudl, F. J. Am. Chem. Soc. 1999, 121, 5611.
39. (a) Hirsch, A.; Lamparth, I.; Grösser, T. J. Am. Chem. Soc. 1994, 116, 9386.
40. (b) Lamparth, I.; Maichle-Mössmer, C.; Hirsch, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1607.
41. (c) Camps, X.; Hirsch, A. J. Chem. Soc., Perkins Trans. 1 1997, 1595.
42. (a) Isaacs, L.; Haldimann, R. F.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 2339.
43. (b) Haldimann, R. F.; Klärner, F.-G.; Diederich, F. Chem. Commun. 1997, 237.
44. 15a Because of this difference, we did check carefully the identity and purity of the 9 sample used in our photophysical measurements.
45. Ma, B.; Sun, Y.-P. J. Chem. Soc., Perkin Trans. 2 1996, 2157.
46. (a) Suzuki, T.; Li, Q.; Khemani, K. C.; Wudl, F.; Almarsson, Ö. Science 1991, 254, 1186.
47. (b) Hirsch, A.; Soi, A.; Karfunkel, H. R. Angew. Chem., Int. Ed. Engl. 1992, 31, 766.
48. Fu, K.; Riggs, J. E.; Sun, Y.-P. Unpublished results.
49. (a) Sun, Y.-P.; Bunker, C. E.; Ma, B. J. Am. Chem. Soc. 1994, 116, 9692.
50. (b) Sun, Y.-P.; Ma, B. Chem. Phys. Lett. 1995, 236, 285.
51. (a) Ghosh, H. N.; Pal, H.; Sapre, A. V.; Mittal, J. P. J. Am. Chem. Soc. 1993, 115, 11722.
52. (b) Park, J.; Kim, D.; Suh, Y. D.; Kim, S. K. J. Phys. Chem. 1994, 98, 12715.
53. (c) Ito, O.; Sasaki, Y.; Yoshikawa, Y.; Watanabe, A. J. Phys. Chem. 1995, 99, 9838.
54. (d) Sasaki, Y.; Yoshikawa, Y.; Watanabe, A.; Ito, O. J. Chem. Soc., Faraday Trans. 1995, 91, 2287.
55. Birks, J. B. Photophysics of Aromatic Molecules: Wiley-Interscience: London, 1970.
56. Wudl, F. Acc. Chem. Res. 1992, 25, 157.
57. (a) Hummelen, J. C.; Knight, B. W.; LePeq, F.; Wudl, F. J. Org. Chem. 1995, 60, 532.
58. (b) González, R.; Hummelen, J. C.; Wudl, F. J. Org. Chem. 1995, 60, 2618.
59. (c) Janssen, R. A.; Hummelen, J. C.; Wudl, F. J. Am. Chem. Soc. 1995, 117, 544.
60. Hirsch, A.; Lamparth, I.; Karfunkel, H. R. Angew. Chem., Int. Ed. Engl. 1994, 33, 437.