Photoinduced electron transfer in covalently linked 1,8-naphthalimide/viologen systems

Journal of Physical Chemistry A

Volumn 104, Issue 29, 2000, Pages 6778-6785

  Le, Thao P ^a   Rogers, Joy E ^a   Kelly, Lisa A ^a  

^a UNIVERSITY OF MARYLAND BALTIMORE COUNTY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; ELECTRON TRANSITIONS; FLUORESCENCE; MATHEMATICAL MODELS; PH EFFECTS; PHOTOLYSIS; RATE CONSTANTS; SOLUTIONS; SYNTHESIS (CHEMICAL);

ELECTRON TRANSFER; INTRAMOLECULAR QUENCHING; NAPHTHALIMIDE; POLYMETHYLENE; PYRIDINIUM; STERN VOLMER ANALYSIS; VIOLOGEN;

CHROMOPHORES;

EID: 0034224241     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp000855y     Document Type: Article

References (48)

1. Wasielewski, M. R. Chem. Rev. 1992, 92, 435-461.
2. Gust, D.; Moore, T. A.; Moore, A. L. Acc. Chem. Res. 1993, 26, 198-205.
3. Closs, G. L.; Miller, J. R. Science 1988, 240, 440-447.
4. Warman, J. M.; Smit, K. J.; de Haas, M. P.; Jonker, S. A.; Paddon-Row, M. N.; Oliver, A. M.; Kroon, J.; Oevering, H.; Verhoeven, J. W. J. Phys. Chem. 1991, 95, 1979-1987.
5. Paddon-Row, M. N.; Oliver, A. M.; Warman, J. M.; Smit, K. J.; de Haas, M. P.; Oevering, H.; Verhoeven, J. W. J. Phys. Chem. 1988, 92, 6958-6962.
6. Oliver, A. M.; Craig, D. C.; Paddon-Row, M. N.; Kroon, J.; Verhoeven, J. W. Chem. Phys. Lett. 1988, 150, 366-373.
7. Jones, G.; Lu, L. N.; Fu, H.; Farahat, C. W.; Oh, C.; Greenfield, S. R.; Gosztola, D. J.; Wasielewski, M. R. J. Phys. Chem. B 1999, 103, 572-581.
8. Mishra, A. K.; Chandrasekar, R.; Faraggi, M.; Klapper, M. H. J. Am. Chem. Soc. 1994, 116, 1414-1422.
9. Isied, S. S.; Ogawa, M. Y.; Wishart, J. F. Chem. Rev. 1992, 92, 381-394.
10. Siemiarczuk, A.; McIntosh, A. R.; Ho, T. F.; Stillman, M. J.; Roach, K. J.; Weedon, A. C.; Bolton, J. R.; Connolly, J. S. J. Am. Chem. Soc. 1983, 105, 7224-7230.
11. Mataga, N.; Karen, A.; Okada, T.; Nishitani, S.; Kurata, N.; Sakada, Y.; Misumi, S. J. Phys. Chem. 1984, 88, 5138-5141.
12. Park, J. W.; Lee, B. A.; Lee, S. Y. J. Phys. Chem. B 1998, 102, 8209-8215.
13. Yonemoto, E. H.; Saupe, G. B.; Schmehl, R. H.; Hubig, S. M.; Riley, R. L.; Iverson, B. L.; Mallouk, T. E. J. Am. Chem. Soc. 1994, 116, 4786-4795.
14. Yonemura, H.; Kasahara, M.; Saito, H.; Nakamura, H.; Matsuo, T. J. Phys. Chem. 1992, 96, 5765-5770.
15. Yonemura, H.; Norjiri, T.; Matsuo, T. Chem. Lett. 1994, 2097-2100.
16. Toki, A.; Yonemura, H.; Matsuo, T. Bull. Chem. Soc. Jpn. 1993, 66, 3382.
17. Yonemura, H.; Nakamura, H.; Matsuo, T. Chem. Phys. Lett. 1989, 155, 157-161.
18. Yonemura, H.; Nakamura, H.; Matsuo, T. Chem. Phys. 1992, 162, 69-78.
19. Yonemoto, E. H.; Kim, Y.; Schmehl, R. H.; Wallin, J. O.; Shoulders, B. A.; Richardson, B. R.; Haw, J. F.; Mallouk, T. E. J. Am. Chem. Soc. 1994, 116, 10557-10563.
20. Dupuis, B.; Michaut, C.; Jouanin, I.; Delaire, J.; Robin, P.; Feneyrou, P.; Dentan, V. Chem. Phys. Lett. 1999, 300, 169-176.
21. Batteas, J. D.; Harriman, A.; Kanda, Y.; Malaga, N.; Nowak, A. K. J. Am. Chem. Soc. 1990, 112, 126-133.
22. Harriman, A.; Porter, G.; Wilowska, A. J. Chem. Soc., Faraday Trans. 2 1984, 80, 191-204.
23. Noda, S.; Hosono, H.; Okura, L; Yamamoto, Y.; Inoue, Y. J. Photochem. Photobiol., A: Chem. 1990, 53, 423-429.
24. Noda, S.; Hosono, H.; Okura, L; Yamamoto, Y.; Inoue, Y. J. Chem. Soc., Faraday Trans. 1990, 50, 811-814.
25. Viehbeck, A.; Goldberg, M. J.; Kovac, C. A. J. Electrochem. Soc. 1990, 137, 1460-1466.
26. Saito, L; Takayama, M.; Sugiyama, H.; Nakatani, K. J. Am. Chem. Soc. 1995, 117, 6406-6407.
27. Saito, I.; Takayama, M. J. Am. Chem. Soc. 1995, 117, 5590-5591.
28. Rogers, J. E.; Weiss, S. J.; Kelly, L. A. J. Am. Chem. Soc. 2000, 122, 427-436.
29. Van Dijk, S. I.; Groen, C. P.; Hard, F.; Brouwer, A. M.; Verhoeven, J. W. J. Am. Chem. Soc. 1996, 118, 8425-8532.
30. Kelly, L. A.; Rodgers, M. A. J. J. Phys. Chem. 1994, 98, 6386-6391.
31. Kelly, L. A.; Trunk, J. G.; Polewski, K.; Sutherland, J. C. Rev. Sci. Instrum. 1995, 66, 1496-1498.
32. Kelly, L. A.; Trunk, J. G.; Sutherland, J. C. Rev. Sci. Instrum. 1997, 68, 2279-2286.
33. Rogers, J. E.; Kelly, L. A. J. Am. Chem. Soc. 1999, 121, 3854-3861.
34. Watanabe, T.; Honda, K. J. Phys. Chem. 1982, 86, 2617-2619.
35. o = -1.01 V vs NHE).
36. Bird, C. L.; Kuhn, A. T. Chem. Soc. Rev. 1981, 10, 49-82.
37. +/Fc couple in aqueous solution (Sawyer, D. T.; Sobkowiak, A.; Roberts, J. I. Electrochemistry for Chemists, 2nd ed.; Wiley-Interscience: New York, 1995; p 203), along with our measured half-wave potential for the ferrocene/ferrocenium couple (0.43 V vs Ag/AgCl), we estimate the viologen-centered reductions to be -0.42 and -0.86 V vs NHE.
38. Wardman, P. J. Phys. Chem. Ref. Data 1989, 18, 1637-1723.
39. Greenfield, S. R.; Svec, W. A.; Gosztola, D.; Wasielewski, M. R. J. Am. Chem. Soc. 1996, 118, 6767-6777.
40. DeSilva, A. P.; Gunaratne, H. Q. N.; Habib-Jiwan, J.-L.; McCoy, C. P.; Rice, T. E.; Soumillion, J.-P. Angew. Chem., Int. Ed. Engl. 1995, 34, 1728-1731.
41. Korol'kova, N. V.; Val'kova, G. A.; Shigorin, D. N.; Shigalevskii, V. A.; Vostrova, V. N. Russ. J. Phys. Chem. 1990, 64, 206-209.
42. Wintgens, V.; Valet, P.; Kossanyi, J.; Biczok, L.; Demeter, A.; Berces, T. J. Chem. Soc., Faraday Trans. 1994, 90, 411-422.
43. Aveline, B. M.; Matsugo, S.; Redmond, R. W. J. Am. Chem. Soc. 1997, 119, 11785-11795.
44. The fluorescence lifetime was measured for C3py (Figure 5). Since the fluorescence quantum yields of C2py-C6py were identical, a singletstate lifetime of 2.46 ns was used for all of the compounds within the Cxpy series.
45. Newton, M. D.; Sutin, N. Annu. Rev. Phys. Chem. 1984, 35, 437-480.
46. Marcus, R. A.; Sutin, N. Biochim. Biophys. Acta 1985, 811, 265-322.
47. Marcus, R. A. J. Chem. Phys. 1965, 43, 679-701.
48. s were found to range from 1.08 to 1.23 Å for spheres separated by 2-5 methylwnes. Thus, it is assumed that deviation from the predicted exponential dependence (eq 5) is negligible.