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Volumn 106, Issue 10, 2002, Pages 2244-2255

Substituent and solvent effects on the nature of the transitions of pyrenol and pyranine. Identification of an intermediate in the excited-state proton-transfer reaction

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC HYDROCARBONS; ELECTRON TRANSITIONS; GROUND STATE; HYDROGEN BONDS; PROTONS; SUBSTITUTION REACTIONS;

EID: 0037076076     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0125606     Document Type: Article
Times cited : (99)

References (86)
  • 2
    • 0000892661 scopus 로고
    • Weller, A.Z. Elektrochem. 1952, 56, 662. Avigal, I.; Feitelson, J.; Ottolenghi, M. J. Chem. Phys. 1969, 50, 2614. Rosenberg, J.L.; Brinn, I. J. Phys. Chem. 1972, 76, 3558.
    • (1952) Elektrochem. , vol.56 , pp. 662
    • Weller, A.Z.1
  • 3
    • 0011142924 scopus 로고
    • Weller, A.Z. Elektrochem. 1952, 56, 662. Avigal, I.; Feitelson, J.; Ottolenghi, M. J. Chem. Phys. 1969, 50, 2614. Rosenberg, J.L.; Brinn, I. J. Phys. Chem. 1972, 76, 3558.
    • (1969) J. Chem. Phys. , vol.50 , pp. 2614
    • Avigal, I.1    Feitelson, J.2    Ottolenghi, M.3
  • 4
    • 0001354497 scopus 로고
    • Weller, A.Z. Elektrochem. 1952, 56, 662. Avigal, I.; Feitelson, J.; Ottolenghi, M. J. Chem. Phys. 1969, 50, 2614. Rosenberg, J.L.; Brinn, I. J. Phys. Chem. 1972, 76, 3558.
    • (1972) J. Phys. Chem. , vol.76 , pp. 3558
    • Rosenberg, J.L.1    Brinn, I.2
  • 7
    • 0011082177 scopus 로고
    • Förster, T.Z. Elektrochem. 1950, 54, 142. Jaffé, H.H.; Lloyd Jones, H. J. Org. Chem. 1965, 30, 1965. Grabowski, Z.R.; Grabowska, A.Z. Phys. Chem. N.F. (Wiesbaden) 1976, 101, 197. Grabowski, Z.R.; Rubaszewska, W. J. Chem. Soc., Faraday Trans. 1 1977, 73, 11. Robinson, G.W. J. Phys. Chem. 1991, 95, 10386. Wehry, E.L.; Rogers, L.B. J. Am. Chem. Soc. 1965, 87, 4234.
    • (1950) Elektrochem. , vol.54 , pp. 142
    • Förster, T.Z.1
  • 8
    • 0011151588 scopus 로고
    • Förster, T.Z. Elektrochem. 1950, 54, 142. Jaffé, H.H.; Lloyd Jones, H. J. Org. Chem. 1965, 30, 1965. Grabowski, Z.R.; Grabowska, A.Z. Phys. Chem. N.F. (Wiesbaden) 1976, 101, 197. Grabowski, Z.R.; Rubaszewska, W. J. Chem. Soc., Faraday Trans. 1 1977, 73, 11. Robinson, G.W. J. Phys. Chem. 1991, 95, 10386. Wehry, E.L.; Rogers, L.B. J. Am. Chem. Soc. 1965, 87, 4234.
    • (1965) J. Org. Chem. , vol.30 , pp. 1965
    • Jaffé, H.H.1    Lloyd Jones, H.2
  • 9
    • 2342545049 scopus 로고
    • Förster, T.Z. Elektrochem. 1950, 54, 142. Jaffé, H.H.; Lloyd Jones, H. J. Org. Chem. 1965, 30, 1965. Grabowski, Z.R.; Grabowska, A.Z. Phys. Chem. N.F. (Wiesbaden) 1976, 101, 197. Grabowski, Z.R.; Rubaszewska, W. J. Chem. Soc., Faraday Trans. 1 1977, 73, 11. Robinson, G.W. J. Phys. Chem. 1991, 95, 10386. Wehry, E.L.; Rogers, L.B. J. Am. Chem. Soc. 1965, 87, 4234.
    • (1976) Phys. Chem. N.F. (Wiesbaden) , vol.101 , pp. 197
    • Grabowski, Z.R.1    Grabowska, A.Z.2
  • 10
    • 0002028854 scopus 로고
    • Förster, T.Z. Elektrochem. 1950, 54, 142. Jaffé, H.H.; Lloyd Jones, H. J. Org. Chem. 1965, 30, 1965. Grabowski, Z.R.; Grabowska, A.Z. Phys. Chem. N.F. (Wiesbaden) 1976, 101, 197. Grabowski, Z.R.; Rubaszewska, W. J. Chem. Soc., Faraday Trans. 1 1977, 73, 11. Robinson, G.W. J. Phys. Chem. 1991, 95, 10386. Wehry, E.L.; Rogers, L.B. J. Am. Chem. Soc. 1965, 87, 4234.
    • (1977) J. Chem. Soc., Faraday Trans. 1 , vol.73 , pp. 11
    • Grabowski, Z.R.1    Rubaszewska, W.2
  • 11
    • 0001199469 scopus 로고
    • Förster, T.Z. Elektrochem. 1950, 54, 142. Jaffé, H.H.; Lloyd Jones, H. J. Org. Chem. 1965, 30, 1965. Grabowski, Z.R.; Grabowska, A.Z. Phys. Chem. N.F. (Wiesbaden) 1976, 101, 197. Grabowski, Z.R.; Rubaszewska, W. J. Chem. Soc., Faraday Trans. 1 1977, 73, 11. Robinson, G.W. J. Phys. Chem. 1991, 95, 10386. Wehry, E.L.; Rogers, L.B. J. Am. Chem. Soc. 1965, 87, 4234.
    • (1991) J. Phys. Chem. , vol.95 , pp. 10386
    • Robinson, G.W.1
  • 12
    • 0001584716 scopus 로고
    • Förster, T.Z. Elektrochem. 1950, 54, 142. Jaffé, H.H.; Lloyd Jones, H. J. Org. Chem. 1965, 30, 1965. Grabowski, Z.R.; Grabowska, A.Z. Phys. Chem. N.F. (Wiesbaden) 1976, 101, 197. Grabowski, Z.R.; Rubaszewska, W. J. Chem. Soc., Faraday Trans. 1 1977, 73, 11. Robinson, G.W. J. Phys. Chem. 1991, 95, 10386. Wehry, E.L.; Rogers, L.B. J. Am. Chem. Soc. 1965, 87, 4234.
    • (1965) J. Am. Chem. Soc. , vol.87 , pp. 4234
    • Wehry, E.L.1    Rogers, L.B.2
  • 13
    • 33845184365 scopus 로고
    • For reviews, see: Barbara, P.F.; Walsh, P.K.; Brus, L.E. J. Phys. Chem. 1989, 93, 29. Syage, J. J. Phys. Chem. 1995, 99, 5772. See also the special issues: J. Phys. Chem. 1991, 95, 25; Chem. Phys. 1989, 136, 2; Ber. Bunsen-Ges. Phys. Chem. 1998, 102, 3.
    • (1989) J. Phys. Chem. , vol.93 , pp. 29
    • Barbara, P.F.1    Walsh, P.K.2    Brus, L.E.3
  • 14
    • 0042105353 scopus 로고
    • For reviews, see: Barbara, P.F.; Walsh, P.K.; Brus, L.E. J. Phys. Chem. 1989, 93, 29. Syage, J. J. Phys. Chem. 1995, 99, 5772. See also the special issues: J. Phys. Chem. 1991, 95, 25; Chem. Phys. 1989, 136, 2; Ber. Bunsen-Ges. Phys. Chem. 1998, 102, 3.
    • (1995) J. Phys. Chem. , vol.99 , pp. 5772
    • Syage, J.1
  • 15
    • 0042139402 scopus 로고
    • For reviews, see: Barbara, P.F.; Walsh, P.K.; Brus, L.E. J. Phys. Chem. 1989, 93, 29. Syage, J. J. Phys. Chem. 1995, 99, 5772. See also the special issues: J. Phys. Chem. 1991, 95, 25; Chem. Phys. 1989, 136, 2; Ber. Bunsen-Ges. Phys. Chem. 1998, 102, 3.
    • (1991) J. Phys. Chem. , vol.95 , pp. 25
  • 16
    • 84914765086 scopus 로고
    • For reviews, see: Barbara, P.F.; Walsh, P.K.; Brus, L.E. J. Phys. Chem. 1989, 93, 29. Syage, J. J. Phys. Chem. 1995, 99, 5772. See also the special issues: J. Phys. Chem. 1991, 95, 25; Chem. Phys. 1989, 136, 2; Ber. Bunsen-Ges. Phys. Chem. 1998, 102, 3.
    • (1989) Chem. Phys. , vol.136 , pp. 2
  • 17
    • 0043141278 scopus 로고    scopus 로고
    • For reviews, see: Barbara, P.F.; Walsh, P.K.; Brus, L.E. J. Phys. Chem. 1989, 93, 29. Syage, J. J. Phys. Chem. 1995, 99, 5772. See also the special issues: J. Phys. Chem. 1991, 95, 25; Chem. Phys. 1989, 136, 2; Ber. Bunsen-Ges. Phys. Chem. 1998, 102, 3.
    • (1998) Ber. Bunsen-Ges. Phys. Chem. , vol.102 , pp. 3
  • 18
    • 0001139129 scopus 로고
    • Vander Donckt, E. Prog. React. Kinet. 1961, 1, 187. Jackson, G.; Porter, G. Proc. R. Soc. 1961, A200, 13. Dickens, P.G.; Linett, J.W. Quart. Rev. Chem. Soc. 1957, 11, 291. Salem, L. Electrons in Chemical Reactions; Wiley: New York, 1982.
    • (1961) Prog. React. Kinet. , vol.1 , pp. 187
    • Vander Donckt, E.1
  • 19
    • 0002473741 scopus 로고
    • Vander Donckt, E. Prog. React. Kinet. 1961, 1, 187. Jackson, G.; Porter, G. Proc. R. Soc. 1961, A200, 13. Dickens, P.G.; Linett, J.W. Quart. Rev. Chem. Soc. 1957, 11, 291. Salem, L. Electrons in Chemical Reactions; Wiley: New York, 1982.
    • (1961) Proc. R. Soc. , vol.A200 , pp. 13
    • Jackson, G.1    Porter, G.2
  • 20
    • 0010472257 scopus 로고
    • Vander Donckt, E. Prog. React. Kinet. 1961, 1, 187. Jackson, G.; Porter, G. Proc. R. Soc. 1961, A200, 13. Dickens, P.G.; Linett, J.W. Quart. Rev. Chem. Soc. 1957, 11, 291. Salem, L. Electrons in Chemical Reactions; Wiley: New York, 1982.
    • (1957) Quart. Rev. Chem. Soc. , vol.11 , pp. 291
    • Dickens, P.G.1    Linett, J.W.2
  • 21
    • 0003422709 scopus 로고
    • Wiley: New York
    • Vander Donckt, E. Prog. React. Kinet. 1961, 1, 187. Jackson, G.; Porter, G. Proc. R. Soc. 1961, A200, 13. Dickens, P.G.; Linett, J.W. Quart. Rev. Chem. Soc. 1957, 11, 291. Salem, L. Electrons in Chemical Reactions; Wiley: New York, 1982.
    • (1982) Electrons in Chemical Reactions
    • Salem, L.1
  • 24
    • 0000296625 scopus 로고
    • Timoneda J.; Hynes, J.T. J. Phys. Chem. 1991, 95, 10431. Staib, A.; Hynes, J.T.; Borgis, D. J. Chem. Phys. 1995, 102, 2487. Ando, K.; Hynes, J.T. J. Phys. Chem. 1997, 101, 10464. Ando, K.; Hynes, J.T. J. Phys. Chem. A, 1999, 103, 10398.
    • (1991) J. Phys. Chem. , vol.95 , pp. 10431
    • Timoneda, J.1    Hynes, J.T.2
  • 25
    • 27844452636 scopus 로고
    • Timoneda J.; Hynes, J.T. J. Phys. Chem. 1991, 95, 10431. Staib, A.; Hynes, J.T.; Borgis, D. J. Chem. Phys. 1995, 102, 2487. Ando, K.; Hynes, J.T. J. Phys. Chem. 1997, 101, 10464. Ando, K.; Hynes, J.T. J. Phys. Chem. A, 1999, 103, 10398.
    • (1995) J. Chem. Phys. , vol.102 , pp. 2487
    • Staib, A.1    Hynes, J.T.2    Borgis, D.3
  • 26
    • 0031553352 scopus 로고    scopus 로고
    • Timoneda J.; Hynes, J.T. J. Phys. Chem. 1991, 95, 10431. Staib, A.; Hynes, J.T.; Borgis, D. J. Chem. Phys. 1995, 102, 2487. Ando, K.; Hynes, J.T. J. Phys. Chem. 1997, 101, 10464. Ando, K.; Hynes, J.T. J. Phys. Chem. A, 1999, 103, 10398.
    • (1997) J. Phys. Chem. , vol.101 , pp. 10464
    • Ando, K.1    Hynes, J.T.2
  • 27
    • 0000991264 scopus 로고    scopus 로고
    • Timoneda J.; Hynes, J.T. J. Phys. Chem. 1991, 95, 10431. Staib, A.; Hynes, J.T.; Borgis, D. J. Chem. Phys. 1995, 102, 2487. Ando, K.; Hynes, J.T. J. Phys. Chem. 1997, 101, 10464. Ando, K.; Hynes, J.T. J. Phys. Chem. A, 1999, 103, 10398.
    • (1999) J. Phys. Chem. A, , vol.103 , pp. 10398
    • Ando, K.1    Hynes, J.T.2
  • 28
    • 0033580290 scopus 로고    scopus 로고
    • For the different, albeit related, problem of proton transport in water, see the extensive references in: Marx, D.; Tuckerman, M.E.; Hutter, J.; Parinello, M. Nature 1999, 397, 601. Hynes J.T. Nature 1999, 397, 565.
    • (1999) Nature , vol.397 , pp. 601
    • Marx, D.1    Tuckerman, M.E.2    Hutter, J.3    Parinello, M.4
  • 29
    • 0033580270 scopus 로고    scopus 로고
    • For the different, albeit related, problem of proton transport in water, see the extensive references in: Marx, D.; Tuckerman, M.E.; Hutter, J.; Parinello, M. Nature 1999, 397, 601. Hynes J.T. Nature 1999, 397, 565.
    • (1999) Nature , vol.397 , pp. 565
    • Hynes, J.T.1
  • 36
    • 0001687805 scopus 로고
    • Trainer, A, Ed.; American Institute of Physics: New York
    • Tran-Thi, T.-H.; Gustavsson, T.; Prayer, C.; Pommeret, S.; Hynes, J.T. Chem. Phys. Lett. 2000, 329, 421. Prayer, C.; Tran-Thi, T.-H.; Gustavsson, T. AIP Conference Proceedings 364; Trainer, A, Ed.; American Institute of Physics: New York, 1995; p 333.
    • (1995) AIP Conference Proceedings , vol.364 , pp. 333
    • Prayer, C.1    Tran-Thi, T.-H.2    Gustavsson, T.3
  • 37
    • 0002302524 scopus 로고
    • Pines, E.; Huppert, D. Chem. Phys. Lett. 1986, 126, 88. Pines, E.; Huppert, D.; Agmon, N. J. Chem. Phys. 1988, 88, 5620. See also: Genosar, L; Cohen, B.; Huppert, D. J. Chem. Phys. A 2000, 104, 6689.
    • (1986) Chem. Phys. Lett. , vol.126 , pp. 88
    • Pines, E.1    Huppert, D.2
  • 38
    • 4043110873 scopus 로고
    • Pines, E.; Huppert, D. Chem. Phys. Lett. 1986, 126, 88. Pines, E.; Huppert, D.; Agmon, N. J. Chem. Phys. 1988, 88, 5620. See also: Genosar, L; Cohen, B.; Huppert, D. J. Chem. Phys. A 2000, 104, 6689.
    • (1988) J. Chem. Phys. , vol.88 , pp. 5620
    • Pines, E.1    Huppert, D.2    Agmon, N.3
  • 39
    • 0034226508 scopus 로고    scopus 로고
    • Pines, E.; Huppert, D. Chem. Phys. Lett. 1986, 126, 88. Pines, E.; Huppert, D.; Agmon, N. J. Chem. Phys. 1988, 88, 5620. See also: Genosar, L.; Cohen, B.; Huppert, D. J. Chem. Phys. A 2000, 104, 6689.
    • (2000) J. Chem. Phys. A , vol.104 , pp. 6689
    • Genosar, L.1    Cohen, B.2    Huppert, D.3
  • 40
    • 0011106451 scopus 로고    scopus 로고
    • Thesis 1997, UFR 926, University of Paris VI, Paris, France
    • Prayer, C., Thesis 1997, UFR 926, University of Paris VI, Paris, France.
    • Prayer, C.1
  • 42
    • 0542443644 scopus 로고
    • See also ref 36
    • Jaffé, H.H. Chem. Rev. 1953, 53, 191. Taft, R.W.; Stanton Ehrenson, Jr.; Lewis, I.C.; Glick R.E. J. Am. Chem. Soc. 1959, 81, 5343. See also ref 36.
    • (1953) Chem. Rev. , vol.53 , pp. 191
    • Jaffé, H.H.1
  • 46
    • 33646797668 scopus 로고
    • Velapoldi, R.A.; Mielenz, K.D. Standard Reference Materials: Fluorescence Standard Reference Material Quinine Sulfate Dihydrate; National Bureau of Standards, U. S. Department of Commerce, 1980; pp 260-64. Weber, G.; Teale, F.W.J. Trans. Faraday Soc. 1958, 54, 640.
    • (1958) Trans. Faraday Soc. , vol.54 , pp. 640
    • Weber, G.1    Teale, F.W.J.2
  • 51
    • 0004318774 scopus 로고
    • Research Laboratory, U. S. Air Force Academy: Colorado Springs, CO
    • Stewart, J.J.P.; Seiler, F.J. MOPAC Program, version 6.0; Research Laboratory, U. S. Air Force Academy: Colorado Springs, CO, 1989.
    • (1989) MOPAC Program, version 6.0
    • Stewart, J.J.P.1    Seiler, F.J.2
  • 60
    • 0011142055 scopus 로고    scopus 로고
    • note
    • - modelling falls for the oscillator strength ratio.
  • 61
    • 0011078193 scopus 로고    scopus 로고
    • note
    • -1 in this special wavelength domain.
  • 66
    • 33845279095 scopus 로고
    • Kamlet, M.J.; Abboud, J.-L.M.; Abraham, M.H.; Taft, R.W.J. Org. Chem. 1983, 48, 2877. Marcus, Y.; Kamlet, M.J.; Taft, R.W. J. Phys. Chem. 1988, 92, 3613.
    • (1988) J. Phys. Chem. , vol.92 , pp. 3613
    • Marcus, Y.1    Kamlet, M.J.2    Taft, R.W.3
  • 69
    • 0011082862 scopus 로고    scopus 로고
    • note
    • a band. A clear example of the difficulty of deconvoluting these transitions is illustrated by the absorption and fluorescence spectra of 3sPyOH in EtOH (Figure 6).
  • 70
    • 0000143634 scopus 로고
    • Kim, H.J.; Hynes, J.T. J. Am. Chem. Soc. 1992, 114, 10508. Kim, H.J.; Hynes, J.T. J. Photochem. Photobiol. A 1997, 105, 337.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 10508
    • Kim, H.J.1    Hynes, J.T.2
  • 72
    • 0033270014 scopus 로고    scopus 로고
    • note
    • a increases with increasing polarity of the solvents. Such dual fluorescence is not observed for pyranine.
  • 74
    • 0009574931 scopus 로고
    • Mulliken, R.S. J. Phys. Chem. 1952, 56, 801. J. Chim. Phys. 1964, 60, 20.
    • (1964) J. Chim. Phys. , vol.60 , pp. 20
  • 75
    • 0011136360 scopus 로고    scopus 로고
    • In a recent experimental study of 3sPYOH in water solution containing 0.6 mol % glycerol over a wide temperature range [Poles, E.; Cohen, B. Huppert, D., Isr. J. Chem. 1999, 39, 347], an unusual non-Arrhenius temperature dependence is found. This was interpreted via a variant of a rate constant model for (electronically nonadiabatic) tunneling electron-transfer reactions [Rips, I.; Jortner, J., J. Chim. Phys.-Chim. Biol. 1987, 87, 2090. Hynes, J.T., J. Phys. Chem. 1986, 90, 3701.] to infer that there is only a very small barrier over and above any effect of solvent dynamics. While an equation of this general type has been discussed for (electronically adiabatic) proton-tunneling reactions [Borgis, D.; Hynes, J.T. Chem. Phys. 1993, 170, 315], in the absence of clear evidence for proton tunneling, a different approach (cf. ref 9b) could be more appropriate. This is under study.
  • 77
    • 33947343179 scopus 로고
    • Bronstead, J.N. Chem. Rev. 1928, 5, 231. Evans, M.G.; Polanyi, M. Trans. Faraday Soc. 1936, 32, 1340. Leffler, J.E. Science 1953, 117, 340.
    • (1928) Chem. Rev. , vol.5 , pp. 231
    • Bronstead, J.N.1
  • 78
    • 33947343179 scopus 로고
    • Bronstead, J.N. Chem. Rev. 1928, 5, 231. Evans, M.G.; Polanyi, M. Trans. Faraday Soc. 1936, 32, 1340. Leffler, J.E. Science 1953, 117, 340.
    • (1936) Trans. Faraday Soc. , vol.32 , pp. 1340
    • Evans, M.G.1    Polanyi, M.2
  • 79
    • 0000288714 scopus 로고
    • Bronstead, J.N. Chem. Rev. 1928, 5, 231. Evans, M.G.; Polanyi, M. Trans. Faraday Soc. 1936, 32, 1340. Leffler, J.E. Science 1953, 117, 340.
    • (1953) Science , vol.117 , pp. 340
    • Leffler, J.E.1
  • 81
    • 5244245983 scopus 로고
    • Hammond, G.S. J. Am. Chem. Soc. 1955, 77, 334. Pross, A. Adv. Phys. Org. Chem. 1977, 14, 69.
    • (1955) J. Am. Chem. Soc. , vol.77 , pp. 334
    • Hammond, G.S.1
  • 82
    • 0002346664 scopus 로고
    • Hammond, G.S. J. Am. Chem. Soc. 1955, 77, 334. Pross, A. Adv. Phys. Org. Chem. 1977, 14, 69.
    • (1977) Adv. Phys. Org. Chem. , vol.14 , pp. 69
    • Pross, A.1
  • 84
    • 33847090497 scopus 로고
    • Fujio, M.; McIver, R.T.; Taft, R.W. J. Am. Chem. Soc. 1981, 103, 4017. McMahon, T.B.; Kebarle, P. J. Am. Chem. Soc. 1977, 99, 2222.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 2222
    • McMahon, T.B.1    Kebarle, P.2
  • 85
    • 0003438540 scopus 로고
    • Cornell University Press: Ithaca, NY
    • Pauling, L. The Nature Of The Chemical Bond, Cornell University Press: Ithaca, NY, 1960. Pross, A.; Radom, L.; Taft, R.W. J. Org. Chem. 1980, 45, 818.
    • (1960) The Nature Of The Chemical Bond
    • Pauling, L.1
  • 86
    • 0000991234 scopus 로고
    • Pauling, L. The Nature Of The Chemical Bond, Cornell University Press: Ithaca, NY, 1960. Pross, A.; Radom, L.; Taft, R.W. J. Org. Chem. 1980, 45, 818.
    • (1980) J. Org. Chem. , vol.45 , pp. 818
    • Pross, A.1    Radom, L.2    Taft, R.W.3


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