Quenching of a photosensitized dye through single-electron transfer from trivalent phosphorus compounds

Journal of Organic Chemistry

Volumn 65, Issue 15, 2000, Pages 4715-4720

  Yasui, Shinro ^a   Tsujimoto, Munekazu ^a   Itoh, Kenji ^b   Ohno, Atsuyoshi ^b,c  

^a TEZUKAYAMA UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

^c FUKUI UNIVERSITY OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORESCENT DYE; PHOSPHORUS DERIVATIVE; RHODAMINE 6G;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; DIFFUSION; ELECTRON TRANSPORT; FLUORESCENCE; PHOTOSENSITIZATION; REACTION ANALYSIS; REACTION TIME;

EID: 0034725938     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000448i     Document Type: Article

References (49)

1. (a) Yasui, S. Rev. Heteroatom Chem. 1995, 12, 145-161 and references therein.
2. (b) Yasui, S.; Shioji, K.; Tsujimoto, M.; Ohno, A. Chem. Lett. 1995, 783-784.
3. (c) Yasui, S.; Tsujimoto, M.; Shioji, K.; Ohno, A. Chem. Ber./Recueil 1997, 130, 1699-1707.
4. (d) Yasui, S.; Shioji, K.; Tsujimoto, M.; Ohno, A. J. Chem. Soc., Perkin Trans. 2 1999, 855-862.
5. (a) Powell, R. D.; Hall, C. D. J. Am. Chem. Soc. 1989, 91, 5403-5404.
6. (b) Pandey, G.; Hajra, S.; Ghorai, M. K. Tetrahedron Lett. 1994, 35, 7837-7840.
7. (a) Ganapathy, S.; Dockery, K. P.; Sopchik, A. E.; Bentrude, W. G. J. Am. Chem. Soc. 1993, 115, 8863-8864.
8. (b) Soma Sekhar, B. B. V.; Bentrude, W. G. Tetrahedron Lett. 1999, 40, 1087-1090.
9. Yasui, S.; Itoh, K.; Tsujimoto, M.; Ohno, A. Chem. Lett. 1998, 1019-1020.
10. Rehm, D.; Weller, A. Isr. J. Chem. 1970, 8, 259-271.
11. (a) Schlesener, C. J.; Amatore, C.; Kochi, J. K. J. Am. Chem. Soc. 1984, 106, 3567-3577.
12. (b) Patz, M.; Kuwahara, Y.; Suenobu, T.; Fukuzumi, S. Chem. Lett. 1997, 567-568.
13. (c) Baciocchi, E.; Lanzalunga, O.; Lapi, A.; Manduchi, L. J. Am. Chem. Soc. 1998, 120, 5783-5787.
14. Grimshaw, J.; Langan, J. R.; Salmon, G. A. J. Chem. Soc., Faraday Trans. 1994, 90, 75-81.
15. Savéant, J.-M. Acc. Chem. Res. 1993, 26, 455-461.
16. Bank, S.; Juckett, D. A. J. Am. Chem. Soc. 1975, 97, 567-573.
17. Gardner, H. C.; Kochi, J. K. J. Am. Chem. Soc. 1975, 97, 1855-1865.
18. Chan, T. W.; Bruice, T. C.; J. Am. Chem. Soc. 1977, 99, 7281-7291.
19. Thomas, M. J.; Foote, C. S. Photochem. Photobiol. 1978, 27, 683-693.
20. Schuster, G. B. J. Am. Chem. Soc. 1979, 101, 5851-5853.
21. Nakashima, N.; Yoshihara, K.; Willig, F. J. Chem. Phys. 1980, 73, 3553-3559.
22. Itoh, K.; Chiyokawa, Y.; Nakao, M.; Honda, K. J. Am. Chem. Soc. 1984, 106, 1620-1627.
23. Lessing, H. E.; von Jena, A.; Reichert, M. Chem. Phys. Lett. 1975, 36, 517-522.
24. +* results only in movement of all points in Figure 2 in unison, providing little influence on the discussion here.
25. ox values of some trivalent phosphorus compounds have been reported in Yasui, S.; Tsujimoto, M.; Okamura, M.; Ohno, A. Bull. Chem. Soc. Jpn. 1998, 71, 927-932.
26. ox values of all compounds used in this work by ourselves using the same solvent as for the Stern-Volmer analysis.
27. (a) Schiavon, G.; Zecchin, S.; Cogoni, G.; Bontempelli, G. Electroanal. Chem. Interfacial Electrochem. 1973, 48, 425-431.
28. (b) Ohmori, H.; Nakai, S.; Masui, M. J. Chem. Soc., Perkin Trans. 1 1978, 1333-1335.
29. (c) Culcasi, M.; Berchadsky, Y.; Gronchi, G.; Tordo, P. J. Org. Chem. 1991, 56, 3537-3542.
30. See, for example, Oevering, H.; Paddon-Row: M. N.; Heppener, M.; Oliver, A. M.; Cotsaris, E.; Verhoeven, J. W.; Hush, N. S. J. Am. Chem. Soc. 1987, 109, 3258-3269.
31. Ballardini, R.; Varani, G.; Indelli, M. T.; Scandola, F.; Balzani, V. J. Am. Chem. Soc. 1978, 100, 7219-7223.
32. Horner, L.; Röttger, F.; Fuchs, H. Chem. Ber. 1963, 96, 3141-3147.
33. Phosphoranyl radicals are oxidized by diaryliodonium and triarylsulfonium salts to give the corresponding phosphonium cations. Kampmeier, J. A.; Nalli, T. W. J. Org. Chem. 1993, 58, 943-949.
34. Yasui, S.; Shioji, K.; Ohno, A.; Yoshihara, M. J. Org. Chem. 1995, 60, 2099-2105.
35. 27 has no influence on photodecomposition of triphenylphosphine (1b) occurring under the irradiation of light from a high-pressure mercury lamp. Yasui, S.; Itoh, K.; Ohno, A. Unpublished result.
36. Korobov, V. E.; Shubin, V. V.; Chibisov, A. K. Chem. Phys. Lett. 1977, 45, 498-501.
37. Wada, M.; Hayase, S.; Fujiwara, M.; Kawaguchi, T.; Iwasaki, T.; Uo, A.; Erabi, T. Bull. Chem. Soc. Jpn. 1996, 69, 655-664.
38. -2.
39. Kayser, R. H.; Young, R. H. Photochem. Photobiol. 1976, 24, 395-401.
40. 32
41. (a) Rathore, R.; Hubig, S. M.; Kochi, J. K. J. Am. Chem. Soc. 1997, 119, 11468-11480.
42. (b) Hubig, S. M.; Kochi, J. K. J. Am. Chem. Soc. 1999, 121, 1688-1694.
43. 0 values for the phosphites 1h-k,m are very close to this border, making the points for these quenchers scattered. See ref 5.
44. (a) Koo, J.-Y.; Schuster, G. B.; J. Am. Chem. Soc. 1977, 99, 6107-6109.
45. (b) Koo, J.-Y.; Schuster, G. B.; J. Am. Chem. Soc. 1978, 100, 4496-4503.
46. Pelizzetti, E.; Mentasti, E.; Pramauro, E.; Inorg. Chem. 1976, 15, 2898-2900.
47. In photochemical processes such as fluorescence quenching, "back SET" takes place in the ground state to regenerate the starting materials. Thus, the term "back SET" used here does not mean the reverse reaction in terms of the principle of microscopic reversibility.
48. +, which could result from the change of the solvent.
49. Yasui, S.; Shioji, K.; Ohno, A.; Yoshihara, M. Chem. Lett. 1993, 1393-1396.