Solvent dependent photophysical properties of dimethoxy curcumin

被引:19
作者
Barik, Atanu [1 ]
Priyadarsini, K. Indira [1 ]
机构
[1] Bhabha Atom Res Ctr, Radiat & Photochem Div, Bombay 400085, Maharashtra, India
关键词
Dimethoxy curcumin; Solvent polarity; Fluorescence; Pulse radiolysis; Triplet state; ANTIOXIDANT/PRO-OXIDANT ACTIVITY; ANTITUMOR AGENTS; UNUSUAL BEHAVIOR; ANALOGS; DYNAMICS; PHOTOCHEMISTRY; FLUORESCENCE; POLARITY; LASER; DYE;
D O I
10.1016/j.saa.2012.12.036
中图分类号
O433 [光谱学];
学科分类号
0703 ; 070302 ;
摘要
Dimethoxy curcumin (DMC) is a methylated derivative of curcumin. In order to know the effect of ring substitution on photophysical properties of curcumin, steady state absorption and fluorescence spectra of DMC were recorded in organic solvents with different polarity and compared with those of curcumin. The absorption and fluorescence spectra of DMC, like curcumin, are strongly dependent on solvent polarity and the maxima of DMC showed red shift with increase in solvent polarity function (Delta f), but the above effect is prominently observed in case of fluorescence maxima. From the dependence of Stokes' shift on solvent polarity function the difference between the excited state and ground state dipole moment was estimated as 4.9 D. Fluorescence quantum yield (phi(f)) and fluorescence lifetime (tau(f)) of DMC were also measured in different solvents at room temperature. The results indicated that with increasing solvent polarity, phi(f) increased linearly, which has been accounted for the decrease in non-radiative rate by intersystem crossing (ISC) processes. (C) 2012 Elsevier B.V. All rights reserved.
引用
收藏
页码:267 / 272
页数:6
相关论文
共 57 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]  
Aggarwal BB, 2007, ADV EXP MED BIOL, V595, P1
[3]   Synthesis and evaluation of electron-rich curcumin analogues [J].
Amolins, Michael W. ;
Peterson, Laura B. ;
Blagg, Brian S. J. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (01) :360-367
[4]   Biological activities of curcumin and its analogues (Congeners) made by man and Mother Nature [J].
Anand, Preetha ;
Thomas, Sherin G. ;
Kunnumakkara, Ajaikumar B. ;
Sundaram, Chitra ;
Harikumar, Kuzhuvelil B. ;
Sung, Bokyung ;
Tharakan, Sheeja T. ;
Misra, Krishna ;
Priyadarsini, Indira K. ;
Rajasekharan, Kallikat N. ;
Aggarwal, Bharat B. .
BIOCHEMICAL PHARMACOLOGY, 2008, 76 (11) :1590-1611
[5]   Concentration dependent antioxidant/pro-oxidant activity of curcumin Studies from AAPH induced hemolysis of RBCs [J].
Banerjee, Arnab ;
Kunwar, A. ;
Mishra, B. ;
Priyadarsini, K. I. .
CHEMICO-BIOLOGICAL INTERACTIONS, 2008, 174 (02) :134-139
[6]   Evidence for the TICT mediated nonradiative deexcitation process for the excited coumarin-1 dye in high polarity protic solvents [J].
Bank, A ;
Kumbhakar, M ;
Nath, S ;
Pal, H .
CHEMICAL PHYSICS, 2005, 315 (03) :277-285
[7]   Effect of solvent polarity on the photophysical properties of coumarin-1 dye [J].
Barik, A ;
Nath, S ;
Pal, H .
JOURNAL OF CHEMICAL PHYSICS, 2003, 119 (19) :10202-10208
[8]  
Barik A., 2002, ORIENT J CHEM, V18, P427
[9]   Molecular dynamics of excited state intramolecular proton transfer: 3-hydroxyflavone in solution [J].
Bellucci, Michael A. ;
Coker, David F. .
JOURNAL OF CHEMICAL PHYSICS, 2012, 136 (19)
[10]  
Bong PH, 2000, B KOREAN CHEM SOC, V21, P81