Influence of Chiral Ionic Liquids on Stereoselective Fluorescence Quenching by Photoinduced Electron Transfer in a Naproxen Dyad

被引:22
作者
Bose, Sayantan [1 ]
Wijeratne, Aruna B. [2 ]
Thite, Aniket [1 ]
Kraus, George A. [1 ]
Armstrong, Daniel W. [2 ]
Petrich, Jacob W. [1 ]
机构
[1] Iowa State Univ, Dept Chem, Ames, IA 50011 USA
[2] Univ Texas Arlington, Dept Chem & Biochem, Arlington, TX 76019 USA
关键词
DYNAMIC SOLVATION; STEREODIFFERENTIATION; DIFFERENTIATION; DISCRIMINATION; COMPLEX; SALTS;
D O I
10.1021/jp904311b
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 a previous study of a naproxen dyad in a pair of N-methylimidazoliummethyl menthylether-NTf2 chiral ionic liquids (J. Phys. Chem. B 2008, 112, 7555), we observed that though intramolecular electron transfer was impeded, a consistent small stereodifferentiation in the fluorescence lifetime of the dyad was obtained. We proposed that this discrimination was purely electronic in nature and did not arise from geometrical effects, which call influence nonradiative rate processes, such as intramolecular electron transfer. In our present work, we have studied the interaction of the same chiral naproxen dyad molecule in both the previously studied menthyl-based NTf2 ionic liquids and also in bis(tertrabutylphosphonium) (TBP) D-,L-tartrate ionic liquids. Unlike in the menthyl-based IL pair, the amount of quenching is different in the bis(TBP) tartrate enantiomeric liquids and the tartrate enantiomers have a different temperature dependence oil the nonradiative rate of the dyad. This chiral discrimination most likely arises from the steric effects of the different conformations of the chiral molecules. We have shown that the viscosity and polarity of the solvents can influence the rate of electron transfer. On the other hand, no Such electron transfer quenching is observed in the menthyl-based NTf2 IL solvents. To our knowledge, this is the first example of chiral ionic liquids inducing a stereoselective fluorescence quenching by photoinduced, intramolecular electron transfer.
引用
收藏
页码:10825 / 10829
页数:5
相关论文
共 39 条
[1]   Wavelength-dependent stereodifferentiation in the fluorescence quenching of asymmetric naphthalene-based dyads by amines [J].
Abad, S ;
Pischel, U ;
Miranda, MA .
JOURNAL OF PHYSICAL CHEMISTRY A, 2005, 109 (12) :2711-2717
[2]   Intramolecular electron transfer in diastereomeric naphthalene amine dyads: a fluorescence and laser flash photolysis study [J].
Abad, S ;
Pischel, U ;
Miranda, MA .
PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, 2005, 4 (01) :69-74
[3]   Influence of chiral ionic liquids on the excited-state properties of naproxen analogs [J].
Adhikary, Ramkrishna ;
Bose, Sayantan ;
Mukherjee, Prasun ;
Thite, Aniket ;
Kraus, George A. ;
Wijeratne, Aruna B. ;
Sharma, Pritesh S. ;
Armstrong, Daniel W. ;
Petrich, Jacob W. .
JOURNAL OF PHYSICAL CHEMISTRY B, 2008, 112 (25) :7555-7559
[4]   EXCITED-STATE INTERACTIONS OF 7-AZAINDOLE WITH ALCOHOL AND WATER [J].
AVOURIS, P ;
YANG, LL ;
ELBAYOUMI, MA .
PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1976, 24 (03) :211-216
[5]   Synthesis of chiral ionic liquids from natural amino acids [J].
Bao, WL ;
Wang, ZM ;
Li, YX .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (02) :591-593
[6]  
BEDDELL CR, 1992, DESIGN DRUGS MACAROM
[7]   Chiral discrimination in the intramolecular abstraction of allylic hydrogens by benzophenone triplets [J].
Boscá, F ;
Andreu, I ;
Morera, IM ;
Samadi, A ;
Miranda, MA .
CHEMICAL COMMUNICATIONS, 2003, (13) :1592-1593
[8]  
Boscá F, 2001, PHOTOCHEM PHOTOBIOL, V74, P637, DOI 10.1562/0031-8655(2001)074<0637:POTNAI>2.0.CO
[9]  
2
[10]  
Boscá F, 2000, PHOTOCHEM PHOTOBIOL, V71, P173, DOI 10.1562/0031-8655(2000)071<0173:APAPSO>2.0.CO