Tuning the mechanism of proton-transfer in a hydroxyflavone derivative

被引:93
作者
Roshal, AD [1 ]
Organero, JA [1 ]
Douhal, A [1 ]
机构
[1] Univ Castilla La Mancha, Fac Ciencias Medio Ambiente, Dept Quim Fis, Secc Quim, Toledo 45071, Spain
关键词
D O I
10.1016/j.cplett.2003.08.008
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
In this Letter, we report on steady-state and time-resolved emission studies of 4'-dimethylaminoflavonol (DAMF) in two families of solvents where we observed a reversible or an irreversible proton motion in the ultrafast formed charge-transfer (CT) state of DMAF. The slower (picosecond) proton-transfer time constant of DMAF compared to the femtosecond one observed in non-substituted 3-hydroxyflavones is due the involvement of an intramolecular CT. For the reversible situation, increasing the polarity of the medium increases the rate of proton motion. (C) 2003 Elsevier B.V. All rights reserved.
引用
收藏
页码:53 / 59
页数:7
相关论文
共 25 条
[1]   Ultrafast measurements of excited state intramolecular proton transfer (ESIPT) in room temperature solutions of 3-hydroxyflavone and derivatives [J].
Ameer-Beg, S ;
Ormson, SM ;
Brown, RG ;
Matousek, P ;
Towrie, M ;
Nibbering, ETJ ;
Foggi, P ;
Neuwahl, FVR .
JOURNAL OF PHYSICAL CHEMISTRY A, 2001, 105 (15) :3709-3718
[2]   PROTON-TRANSFER AND SOLVENT POLARIZATION DYNAMICS IN 3-HYDROXYFLAVONE [J].
BRUCKER, GA ;
SWINNEY, TC ;
KELLEY, DF .
JOURNAL OF PHYSICAL CHEMISTRY, 1991, 95 (08) :3190-3195
[3]  
Bu''nau G. v., 1970, RANG DALESPHARMACOLO, V74, P1294, DOI [10.1002/bbpc.19700741223, DOI 10.1002/BBPC.19700741223]
[4]   REVERSAL OF EXCITATION BEHAVIOR OF PROTON-TRANSFER VS CHARGE-TRANSFER BY DIELECTRIC PERTURBATION OF ELECTRONIC MANIFOLDS [J].
CHOU, PT ;
MARTINEZ, ML ;
CLEMENTS, JH .
JOURNAL OF PHYSICAL CHEMISTRY, 1993, 97 (11) :2618-2622
[5]   Dual fluorescence and intramolecular charge transfer with N-phenylphenanthridinones [J].
Demeter, A ;
Bérces, T ;
Zachariasse, KA .
JOURNAL OF PHYSICAL CHEMISTRY A, 2001, 105 (19) :4611-4621
[6]   Intramolecular excited-state proton transfer and charge transfer fluorescence of a 3-hydroxyflavone derivative in micellar media [J].
Dennison, SM ;
Guharay, J ;
Sengupta, PK .
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 1999, 55 (04) :903-909
[7]   FEMTOSECOND MOLECULAR-DYNAMICS OF TAUTOMERIZATION IN MODEL BASE-PAIRS [J].
DOUHAL, A ;
KIM, SK ;
ZEWAIL, AH .
NATURE, 1995, 378 (6554) :260-263
[8]  
DOUHAL A, 2002, FEMTOCHEMISTERY FEMT
[9]  
DOUHAL A, IN PRESS
[10]  
Douhal A., 1996, CHEM PHYS, V207, P447