6498 J. Phys. Chem. A, Vol. 108, No. 31, 2004
Chou et al.
(12) For examples, see: (a) Studer, S. L.; Brewer, W. E.; Martinez, M.
L.; Chou, P.-T. J. Am. Chem. Soc. 1989, 111, 7643. (b) Chou, P.-T.; Studer,
S. L.; Martinez, M. L.; Orton, E.; Young, M. Photochem. Photobiol. 1991,
53, 587.
(13) Chou, P.-T.; Chen, Y.-C.; Yu, W.-S.; Chou, Y.-H.; Wei, C.-Y.;
Cheng, Y.-M. J. Phys. Chem. A 2001, 105, 1731.
(14) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb,
M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.;
Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A.
D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi,
M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.;
Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick,
D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.;
Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi,
I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.;
Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M.
W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.;
Head-Gordon, M.; Replogle, E. S.; Pople, J. A. GAUSSIAN 98, Revision
A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
References and Notes
(1) In general, it is difficult to distinguish the mechanism between
proton transfer and hydrogen atom transfer reactions. In this review article
we simply adopted the conventional term namely “proton transfer”
throughout the text, which is particularly more suitable in describing the
solvent polarity coupled proton-transfer tautomerism.
(2) For example, see: Studies in Physical and Theoretical Chemistry;
Mu¨ller, A., Ratajack, H., Junge, W., Diemann, E., Eds.; Electron and Proton
Transfer in Chemistry and Biology, Vol. 78; Elsevier: Amsterdam, The
Netherlands, 1992.
(3) (a) Scheiner, S. J. Phys. Chem. A 2000, 104, 5898. (b) Waluk, J.
Conformational Aspects of Intra- and Intermolecular Excited-State Proton
Transfer. In Conformational Analysis of Molecules in Excited States; Waluk,
J., Ed.; Wiley-VCH: New York, 2000. (c) Chou, P. T. J. Chin. Chem. Soc.
2001, 48, 651. (d) Wu, K.-C.; Cheng, Y.-M.; Lin, Y.-S.; Yeh, Y.-S.; Pu,
S.-C.; Hu, Y.-H.; Yu, J.-K.; Chou, P.-T. Chem. Phys. Lett. 2004, 382, 203.
(e) Paterson, M. J.; Robb, M. A.; Blancafort, L.; DeBellis, A. D. J. Am.
Chem. Soc. 2004, 126, 2912. (f) Lochbrunner, S.; Wurzer, A. J.; Riedle, E.
J. Phys. Chem. A 2003, 107, 10580. (g) de Vivie-Riedle, R.; De Waele,
V.; Kurtz, L.; Riedle, E. J. Phys. Chem. A 2003, 107, 10591. (h) Shynkar,
V. V.; Mely, Y.; Duportail, G.; Piemont, E.; Klymchenko, A. S.;
Demchenko, A. P. J. Phys. Chem. A 2003, 107, 9522. (i) Cheng, C.-C.;
Chang, C.-P.; Yu, W.-S.; Hung, F.-T.; Liu, Y.-I.; Wu, G.-R.; Chou, P.-T.
J. Phys. Chem. A 2003, 107, 1459. (j) Lukeman, M.; Wan, P. J. Am. Chem.
Soc. 2003, 125, 1164.
(4) In some ESIPT molecules, the lowest excited singlet state is in an
nπ* configuration, in which ESIPT is prohibited. For a recent review, see
ref 3a.
(5) ESIPT incorporating phenol O-H to a â-carbon atom is not
included in this category, see: Lukeman, M.; Wan, P. J. Am. Chem. Soc.
2002, 124, 9458.
(6) For recent examples, see: (a) Chudoba, C.; Riedle, E.; Pfeiffer,
M.; Elsaesser, T. Chem. Phys. Lett. 1996, 263, 622. (b) Lochbrunner, S.;
Wurzer, A. J.; Riedle, E. J. Chem. Phys. 2000, 112, 10699. (c) Chou, P.-
T.; Chen, Y.-C.; Yu, W.-S.; Chou, Y.-H.; Wei, C.-Y.; Cheng, Y.-M. J.
Phys. Chem. A 2001, 105, 1731. (d) Ameer-Beg S.; Ormson, S. M.; Brown,
R. G.; Matousek, P.; Towrie, M.; Nibbering, E. T. J.; Foggi, P.; Neuwahl,
F. V. R. J. Phys. Chem. A 2001, 105, 3709. (e) Chou, P.-T.; Chen, Y.-C.;
Yu, W.-S.; Cheng, Y.-M. Chem. Phys. Lett. 2001, 340, 89.
(7) For examples, see: (a) McMorrow, D.; Kasha, M. J. Phys. Chem.
1984, 88, 2235. (b) Brucker, G. A.; Kelley, D. F. J. Phys. Chem. 1987, 91,
2856. (c) Brucker, G. A.; Kelley, D. F. J. Phys. Chem. 1987, 91, 2862. (d)
Strandjord, A. J. G.; Barbara, P. F. J. Phys. Chem. 1985, 89, 2355. (e)
Brucker, G. A.; Kelley, D. F.; Swinney, T. C. J. Phys. Chem. 1991, 95,
3190.
(15) (a) Nagaoka, S. I.; Hirota, N.; Sumitani, M.; Yoshihara, K. J. Am.
Chem. Soc. 1983, 105, 4220. (b) Toribio, F.; Catala´n, J.; Amat, F.; Acun˜a,
A. U. J. Phys. Chem. 1983, 87, 817.
(16) Stock, K.; Bizjak, T.; Lochbrunner, S. Chem. Phys. Lett. 2002, 354,
409.
(17) Lippert, E. Z. Naturforsch. 1955, 10a, 541.
(18) Mataga, N.; Kubota, T. Molecular Interactions and Electronic
Spectra; Marcel Dekker: New York, 1970; p 385.
(19) Bilot, L.; Kawski, A. Z. Naturforsch. 1962, 17a, 621.
(20) Liptay, W. Z. Naturforsch. 1965, 20a, 1441.
(21) Lakowicz, J. R. Principles of Fluorescence Spectroscopy; Plenum
Press: New York, 1983.
(22) (a) Nagarajan, V.; Brearley, A. M.; Kang, T. J.; Barbara, P. F. J.
Chem. Phys. 1987, 86, 3183. (b) Barbara, P. F.; Jarzeba, W. AdV. Photochem.
1990, 15, 1.
(23) Horng, M. L.; Gardecki, J. A.; Papazyan, A.; Maroncelli, M. J.
Phys. Chem. 1995, 99, 17311.
(24) Reynolds, L.; Gardecki, J. A.; Frankland, S. J. V.; Horng, M. L.;
Maroncelli, M. J. Phys. Chem. 1996, 100, 10337.
(25) Stock, K.; Bizjak, T.; Lochbrunner, S. Chem. Phys. Lett. 2002, 354,
409.
(26) Marcus, R. A. J. Chem. Phys. 1965, 43, 379.
(27) Marcus, R. A. Annu. ReV. Phys. Chem. 1964, 15, 155.
(28) Marcus, R. A. J. Chem. Phys. 1965, 43, 679.
(29) Marcus, R. A. ReV. Mod. Phys. 1993, 65, 599.
(30) Bordewijk, O. Theory of Electric Polarization; Elsevier: Amster-
dam, The Netherlands, 1978; Vol. 2.
(31) Calef, D. F.; Wolynes, P. G. J. Phys. Chem. 1983, 87, 3387.
(32) Kiefer, P. M.; Hynes, J. T. J. Phys. Chem. A 2002, 106, 1834.
(33) Kiefer, P. M.; Hynes, J. T. J. Phys. Chem. A 2002, 106, 1850.
(34) (a) Weisenborn, P. C. M.; Huizer, A. H.; Varma, C. A. G. O. J.
Chem. Soc., Faraday Trans. 1989, 85, 1895. (b) Blib, B.; Lommatzsch,
U.; Monte, C.; Rettig, W.; Brutschy, B. Chem. Phys. 2000, 254, 407.
(35) Rettig, W.; Zietz, B. Chem. Phys. Lett. 2000, 317, 187.
(36) Rappoport, D.; Furche, F. J. Am. Chem. Soc. 2004, 126, 1279.
(8) (a) Gormin, D.; Kasha, M. Chem. Phys. Lett. 1988, 153, 574. (b)
Heldt, J.; Gormin, D.; Kasha, M. Chem. Phys. 1989, 136, 321.
(9) (a) Chou, P.-T.; Martinez, M. L.; Clements, J. H. J. Phys. Chem.
1993, 97, 2618. (b) Chou, P.-T.; Martinez, M. L.; Clements, J. H. Chem.
Phys. Lett. 1993, 204, 395.
(10) (a) Swinney, T. C.; Kelley, D. F. J. Chem. Phys. 1993, 99, 211.
(b) Parsapour, F.; Kelley, D. F. J. Phys. Chem. 1996, 100, 2791.
(11) Ormson, S. M.; Brown, R. G.; Vollmer, F.; Rettig, W. J. Photochem.
Photobiol. A 1994, 81, 65.