Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Excited State Proton Transfers and Subsequent Electron Rearrangement of Aqueous 6-Hydroxyquinoline

  • Published : 1997.02.20
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Abstract

Aqueous 6-hydroxyquinoline in the first excited singlet state undergoes protonation to the imine group first in 15 ps, then in the time scale of 40 ps deprotonation from the enol group and finally, however, quickly as in 11 ps electron rearrangement to change into a resonance hybrid structure of quinoid-prevailing forms. Despite the fact that the decay time constant is smaller than the formation time constant, fluorescence from excited protropic zwitterion is observed to assign its maximum at 510 nm. The electron rearrangement is basically an intramolecular charge transfer from the deprotonated oxygen atom to the positively charged iminium ring without any notable change in nuclear geometry, producing a zwitterionic quinoid structure with much a smaller electric dipole moment than the zwitterionic protropic species. This photoproduct formed by consecutive excited state proton and electron transfers shows a smaller dipole moment in S1 than in S0 and a hypsochromic shift although its S1 state has (π, π*) character.

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References

  1. Modern Molecular Photochemistry Turro, N. J.
  2. Adv. Photochem. v.10 Klopffer, W.
  3. Anal. Chim. Acta v.303 Verdasco, G.;Martin, M. A.;del Castillo, B.;Lopez-Alvarado, P.;Menendez, J. C.
  4. Inorg. Chem. v.34 Cummings, S. D.;Eisenberg, R.
  5. Spectrochim. Acta v.51 Linares, R. M.;Gonzalez, A.;Ayala, J. H.;Afonso, A. M.;Gonzalez, V.
  6. J. Phys. Chem. v.98 Park, H.-R.;Mayer, B.;Wolschann, P.;Kohler, G.
  7. J. Phys. Chem. v.99 Douhal, A.;Amat-Guerri, F.;Acuna, A. U.
  8. J. Am. Chem. Soc. v.117 Shafirovich, V. Y.;Courtney, S. H.;Ya, N.
  9. J. Phys. Chem. v.99 Hassoon, S.;Neckers, D. C.
  10. J. Phys. Chem. v.100 Hara, K.;Kometani, K.;Kajimoto, O.
  11. Chem. Phys. Lett. v.235 Mac, M.;Najbar, J.;Wirz, J.
  12. J. Photochem. Photobiol. A: Chem. v.97 Gao, M.;Hill, R. H.
  13. J. Am. Chem. Soc. v.118 Niu, Y.;Christophy, E.;Pisano, P. J.;Zhang, Y.;Hossenlopp, J. M.
  14. J. Chem. Soc., Perkin Trans. v.2 Castellan, A.;Grelier, S.;Kessab, L.;Nourmamode, A.;Hannachi, Y.
  15. J. Chem. Phys. v.103 Benjamin, I.
  16. FEBS Lett. v.378 Karge, M.;Irrgang, K.-D.;Sellin, S.;Feinaugle, R.;Liu, B.;Eckert, H.-J.;Eichler, H. J.;Renger, G.
  17. Adv. Chem. Phys. v.47 Huppert, D.;Gutman, M.;Kaufmann, K. J.
  18. Chem. Phys. Lett. v.240 Chudoba, C.;Lutgen, S.;Jentzsch, T.;Riedle, E.;Woerner, M.;Elsaesser, T.
  19. J. Phys. Chem. v.99 Syage, J. A.
  20. J. Phys. Chem. v.100 Logunov, S. L.;El-Sayed, M. A.;Song, L.;Lanyi, J. K.
  21. Application Of Time-Resolved Optical Spectroscopy Bruckner, V.;Feller, K.-H.;Grummt, U.-W.
  22. Bull. Chem. Soc. Jpn. v.68 Nijhawan, M.;Chauhan, R. S.;Kakkar, L. R.
  23. Anal. Chim. Acta v.316 Djane, N.-K.;Malcus, F.;Martins, E.;Sawula, G.;Johansson, G.
  24. Appl. Phys. Lett. v.64 Burrows, P. E.;Forrest, S. R.
  25. Mater. Sci. Technol. v.11 Rompf, C.;Ammermann, D.;Kowalsky, W.
  26. J. Appl. Phys. v.79 Matsumura, M.;Akai, T.;Saito, M.;Kimura, T.
  27. J. Phys. Chem. v.100 Douhal, A.;Dabrio, J.;Sastre, R.
  28. J. Phys. Chem. v.99 Kim, T. G.;Lee, S.-I.;Jang, D.-J.;Kim, Y.
  29. J. Phys. Chem. v.99 Lee, S.-I.;Jang, D.-J.
  30. J. Phys. Chem. v.97 Lavin, A.;Collins, S.
  31. Bull. Korean Chem. Soc. v.13 Kang, W.-K.;Cho, S.-J.;Lee, M.;Kim, D.-H.;Ryoo, R.;Jung, K.-H.;Jang, D.-J.
  32. J. Phys. Chem. v.98 Bardez, E.;Chatelain, A.;Larrey, B.;Valeur, B.
  33. J. Acta Cryst. v.C42 Lakes, P. E.;Rettig, S. J.;Trotter, J.
  34. J. Med. Chem. v.20 Shah, K. J.;Coats, E. A.
  35. Naturforsch v.44c Chung, K. H.;Cho, K. Y.;Asami, Y.;Takahashi, N.;Yoshida, S. Z.
  36. J. Chem. Soc. no.A Mason, S. F.;Philp, J.;Smith, B. E.
  37. Jpn. J. Cancer Res. v.85 Yoshinari, T.;Okada, H.;Yamada, A.;Uemura, D.;Oka, H.;Suda, H.;Okura, A.
  38. J. Am. Chem. Soc. v.103 Konishi, M.;Ohkuma, H.;Sakai, F.;Tsuno, T.;Koshiyama, H.;Naito, T.;Kawaguchi, H.
  39. J. Phys. Chem. v.95 Held, A.;Plusquellic, D. F.;Tomer, J. L.;Pratt, D. W.
  40. Inorg. Chem. v.32 Leeaphon, M.;Rohl, K.;Thomas, R. J.;Fanwick, P. E.;Walton, R. A.
  41. J. Photochem. Photobiol. A: Chem. v.80 Park, J.;Kang, W.-K.;Ryoo, R.;Jung, K.-H.;Jang, D.-J.
  42. J. Chem. Phys. v.47 Siebrand, W.