The Effect of a Mild Base on Curcumin in Methanol and Ethanol

被引:31
作者
Erez, Yuval [1 ]
Presiado, Itay [1 ]
Gepshtein, Rinat [1 ]
Huppert, Dan [1 ]
机构
[1] Tel Aviv Univ, Sch Chem, Raymond & Beverly Sackler Fac Exact Sci, IL-69978 Tel Aviv, Israel
基金
以色列科学基金会;
关键词
PROTON-TRANSFER; SOLVATION DYNAMICS; ATOM TRANSFER; PHOTOPHYSICS;
D O I
10.1021/jp300003a
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070305 [高分子化学与物理];
摘要
Steady-state and time-resolved emission techniques were employed to study the effect of acetate, a mild base, on the luminescence of curcumin in methanol and ethanol. We found that the steady-state emission intensity as well as the average fluorescence decay time are reduced by a factor of 5 when the acetate concentration is raised to about 1.8 M. We attribute this large effect to an excited-state proton transfer (ESPT) from the acidic groups of curcumin to the acetate anion. We analyze the experimental data in terms of an ESPT reaction occurring between a photoacid and a base.
引用
收藏
页码:2039 / 2048
页数:10
相关论文
共 27 条
[1]
Excited-State Intramolecular Hydrogen Atom Transfer and Solvation Dynamics of the Medicinal Pigment Curcumin [J].
Adhikary, Ramkrishna ;
Mukherjee, Prasun ;
Kee, Tak W. ;
Petrich, Jacob W. .
JOURNAL OF PHYSICAL CHEMISTRY B, 2009, 113 (15) :5255-5261
[2]
Determination of acidity constants of curcumin in aqueous solution and apparent rate constant of its decomposition [J].
Bernabé-Pineda, M ;
Ramírez-Silva, MT ;
Romero-Romo, M ;
Gonzádlez-Vergara, E ;
Rojas-Hernández, A .
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2004, 60 (05) :1091-1097
[3]
Bong PH, 2000, B KOREAN CHEM SOC, V21, P81
[4]
SPECTRAL AND PHOTOCHEMICAL PROPERTIES OF CURCUMIN [J].
CHIGNELL, CF ;
BILSKI, P ;
RESZKA, KJ ;
MOTTEN, AG ;
SIK, RH ;
DAHL, TA .
PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1994, 59 (03) :295-302
[5]
Diffusion-limited acid-base nonexponential dynamics [J].
Cohen, B ;
Huppert, D ;
Agmon, N .
JOURNAL OF PHYSICAL CHEMISTRY A, 2001, 105 (30) :7165-7173
[6]
Parallel proton transfer pathways in aqueous acid-base reactions [J].
Cox, M. J. ;
Bakker, H. J. .
JOURNAL OF CHEMICAL PHYSICS, 2008, 128 (17)
[7]
Distance-Dependent Proton Transfer along Water Wires Connecting Acid-Base Pairs [J].
Cox, M. Jocelyn ;
Timmer, Rutger L. A. ;
Bakker, Huib J. ;
Park, Soohyung ;
Agmon, Noam .
JOURNAL OF PHYSICAL CHEMISTRY A, 2009, 113 (24) :6599-6606
[8]
Temperature Dependence of the Fluorescence Properties of Curcumin [J].
Erez, Yuval ;
Presiado, Itay ;
Gepshtein, Rinat ;
Huppert, Dan .
JOURNAL OF PHYSICAL CHEMISTRY A, 2011, 115 (40) :10962-10971
[9]
FISHER C, 1992, ACS SYM SER, V506, P118
[10]
Ultrafast Dynamics of the Excited States of Curcumin in Solution [J].
Ghosh, Rajib ;
Mondal, Jahur A. ;
Palit, Dipak K. .
JOURNAL OF PHYSICAL CHEMISTRY B, 2010, 114 (37) :12129-12143