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DOI: 10.1039/A809483G (Paper) Reference Section for: Phys. Chem. Chem. Phys., 1999, 1, 1859-1865

Hydration effects on the triplet exciplex between 2,3-dihalo-1,4-naphthoquinone and furan studied by steady-state and laser flash photolyses

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Minoru Yamaji, Masanori Kurumi, Hiroko Kimura and Haruo Shizuka

Abstract

Photochemical interactions of triplet 2,3-dibromo- and 2,3-dichloro-1,4-naphthoquinones (DBNQ and DCNQ) with furan in acetonitrile (ACN) and a mixture of ACN and water (4:1 v/v) were investigated by means of product analysis, steady-state and nanosecond laser flash photolysis. The photoproducts of DBNQ and DCNQ in the presence of furan in ACN were 2-bromo- and 2-chloro-3-(2-furyl)-1,4-naphthoquinones with the quantum yields for production (Φpro) of 0.12 and 0.05, respectively, whereas in aqueous ACN, 2,3-dibromo- and 2,3-dichloro-1,4-dihydroxynaphthalenes Φpro=0.12 and 0.17, respectively. By nanosecond laser photolysis at 355 nm, it was found that triplet DBNQ and DCNQ were quenched by furan with rate constants (kq) of 2.0×109 and 3.0×109 d mol-1 s-1 in ACN and 6.1×109 and 6.4×109 d mol s-1 in aqueous ACN, respectively. After depletion of triplet DBNQ and DCNQ, no transient absorption in the region 360–600 nm was observed in ACN while the corresponding anion radicals having molar absorption coefficients (εani) of 7700 and 7900 d mol-1 cm-1 at 400 nm, respectively, were formed in aqueous ACN. The initial interaction of triplet DBNQ and DCNQ with furan in aqueous ACN was found to be electron transfer with efficiencies (αet) of 0.22 and 0.23, respectively, while that in ACN was presumed to be dominated by induced quenching. The deactivation mechanism of triplet DBNQ and DCNQ by furan was discussed from the viewpoint of the free energy changes (ΔG) for electron transfer. It was suggested that the triplet exciplex with weak charge-transfer character played an important role being controlled by the solvation energy in the ΔG term.

References

  1. R. A. Morton, Biochemistry of Quinones, Academic Press, New York, 1965 Search PubMed.
  2. F. L. Crane, in Biological Oxidation, ed. T. P. Singer, Interscience, New York, 1968 Search PubMed.
  3. T. E. King and M. Klingenburg, Electron and Coupled Energy Transfer in Biological Systems, Marcel Dekker, New York, 1971, parts A and B, vol. 1 Search PubMed.
  4. R. H. Thompson, Naturally Occurring Quinones, Academic Press, New York, 2nd edn., 1971 Search PubMed.
  5. A. K. Lamola and N. J. Turro, in Energy Transfer and Organic Photochemistry, Technique of Organic Chemistry, ed. A. Weissenberger, Interscience, New York, 1974, vol. XIV Search PubMed.
  6. R. H. Thompson, in The Chemistry of Quinonoid Compounds, ed. S. Patai, Wiley-Interscience, New York, 1979, part 1 Search PubMed; J. Q. Cambers, in The Chemistry of Quinonoid Compounds, ed. S. Patai, Wiley-Interscience, New York, 1979, part 2 Search PubMed.
  7. K. Maruyama and A. Osuka, in The Chemistry of Quinonoid Compounds, ed. S. Patai and Z. Rappoport, Wiley-Interscience, New York, 1988, vol. 2, ch. 13 Search PubMed.
  8. N. K. Bridge and G. Porter, Proc. R. Soc. London, Ser. A, 1958, 244, 259.
  9. N. K. Bridge and G. Porter, Proc. R. Soc. London, Ser. A, 1958, 244, 276; D. R. Kemp and G. Porter, Proc. Roy. Soc. London, Ser. A, 1971, 326, 117 CAS.
  10. K. Tickle and F. Wilkinson, Trans. Faraday Soc., 1965, 61, 1981 RSC; F. Wilkinson, G. M. Seddon and K. Tickle, Ber. Bunsen-Ges. Phys. Chem., 1968, 72, 315 Search PubMed; J. Nafisi-Movaghar and F. Wilkinson, Trans. Faraday Soc., 1970, 66, 2268 RSC.
  11. S. K. Wong, J. Am. Chem. Soc., 1978, 100, 5488 CrossRef CAS.
  12. E. J. Land, Trans. Faraday Soc., 1969, 65, 2815 RSC; G. J. Fisher and E. J. Land, Photochem. Phytobiol., 1983, 37, 27 Search PubMed.
  13. R. L. Wilson, Trans. Faraday Soc., 1971, 67, 3020 RSC; K. B. Patel and R. L. Wilson, J. Chem. Soc., Faraday Trans. 1, 1973, 69, 814 RSC.
  14. J. McVie, R. S. Sinclair and T. G. Truscott, Photochem. Photobiol., 1979, 29, 395 CAS.
  15. E. Amouyal and R. Bensasson, J. Chem. Soc., Faraday Trans. 1, 1977, 73, 1561 RSC; J.-C. Ronfard-Haret, R. Bensasson and E. Amouyal, J. Chem. Soc., Faraday Trans. 1, 1980, 76, 2432 RSC.
  16. R. Scheere and M. Grätzel, J. Am. Chem. Soc., 1977, 99, 865 CrossRef CAS.
  17. J. Mayor and R. Krasiukianis, J. Chem. Soc., Faraday Trans., 1991, 87, 2943 RSC.
  18. K. Hamanoue and T. Nakayama, Res. Chem. Intermed., 1996, 22, 189 CAS.
  19. J. R. Wagner, J. E. van Lier and L. J. Johnston, Photochem. Photobiol., 1990, 52, 333 CAS.
  20. Y. Takahashi, F. Endoh, H. Ohaku, K. Wakamatsu and T. Miyashi, J. Chem. Soc., Chem. Commun., 1994, 1227 RSC.
  21. T. Melvin, E. Bothe and D. Schulte-Frohlinde, Photochem. Photobiol., 1996, 64, 769 CAS.
  22. I. Amada, M. Yamaji, M. Sase and H. Shizuka, J. Chem. Soc., Faraday Trans., 1995, 91, 2751 RSC.
  23. I. Amada, M. Yamaji, M. Sase and H. Shizuka, Res. Chem. Intermed., 1997, 23, 121 CAS.
  24. I. Amada, M. Yamaji, S. Tsunoda and H. Shizuka, Photochem. Photobiol. A, 1995, 95, 27 CrossRef CAS.
  25. I. Amada, M. Yamaji, M. Sase, H. Shizuka, T. Shimokage and S. Tero-Kubota, Res. Chem. Intermed., 1998, 24, 81 CAS.
  26. T. Shimokage, T. Ikoma, K. Akiyama, S. Tero-Kubota, M. Yamaji and H. Shizuka, J. Phys. Chem. A, 1997, 101, 9253 CrossRef.
  27. D. Bryce-Smith, E. H. Evans, A. Gilbert and H. S. McNeill, J. Chem. Soc., Perkin Trans. 1, 1992, 485 RSC.
  28. K. Maruyama, T. Otsuki and S. Tai, J. Org. Chem., 1985, 50, 52 CrossRef CAS; K. Maruyama and H. Imahori, J. Org. Chem., 1989, 54, 2692 CrossRef CAS; K. Maruyama and H. Imahori, J. Chem. Soc., Perkin Trans. 2, 1990, 257 RSC.
  29. K. Maruyama and T. Otsuki, Chem. Lett., 1977, 851 CAS.
  30. K. Maruyama and T. Otsuki, Bull. Chem. Soc. Jpn., 1977, 50, 3429 CAS.
  31. K. Maruyama, T. Otsuki and H. Tamiaki, Bull. Chem. Soc. Jpn., 1985, 58, 3049 CAS.
  32. M. McElvain and E. L. Engelhardt, J. Am. Chem. Soc., 1944, 66, 1077 CrossRef.
  33. F. Benington, R. D. Morin and L. C. Clark, Jr., J. Org. Chem., 1955, 20, 102 CrossRef CAS.
  34. M. Yamaji, Y. Aihara, T. Itoh, S. Tobita and H. Shizuka, J. Phys. Chem., 1994, 98, 7014 CrossRef CAS.
  35. E. W. Förster, K. H. Grellman and H. Linschitz, J. Am. Chem. Soc., 1973, 95, 3108 CrossRef.
  36. M. Hoshino and M. Koizumi, Bull. Chem. Soc. Jpn., 1972, 45, 2731 CAS.
  37. K. Okada, M. Yamaji and H. Shizuka, J. Chem. Soc., Faraday Trans., 1998, 94, 861 RSC.
  38. M. Yamaji, T. Sekiguchi, M. Hoshino and H. Shizuka, J. Phys. Chem., 1992, 96, 9353 CrossRef CAS.
  39. S. L. Murov, I. Carmichael and G. L. Hug, Handbook of Photochemistry, Marcel Dekker, New York, 2nd edn., 1993 Search PubMed.
  40. T. Tanaka, M. Yamaji and H. Shizuka, J. Chem. Soc., Faraday Trans., 1998, 94, 1179 RSC.
  41. A. Weller, Z. Phys. Chem., 1982, 133, 93 CAS.
  42. D. Rehm and A. Weller, Ber. Bunsen-Ges. Phys. Chem., 1969, 73, 834 Search PubMed.
  43. K. Kikuchi, T. Niwa, Y. Takahashi, H. Ikeda, T. Miyashi and M. Hoshi, Chem. Phys. Lett., 1990, 173, 421 CrossRef CAS; K. Kikuchi, J. Photochem. Photobiol. A, 1992, 65, 149 CrossRef CAS.
  44. M. Born, Z. Phys., 1920, 1, 221.
  45. M. Yamaji, M. Kurumi, H. Kimura and H. Shizuka, unpublished results.
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