A practical enantioselective fluorescent sensor for mandelic acid

被引：152

作者：

Lin, J ^{[1
]}

Hu, QS ^{[1
]}

Xu, MH ^{[1
]}

Pu, L ^{[1
]}

机构：

[1] Univ Virginia, Dept Chem, Charlottesville, VA 22904 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 10期

关键词：

D O I：

10.1021/ja011971x

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel optically active bisbinaphthyl fluorescent sensor, (S,S)- or (R,R)-1, is designed for the recognition of chiral α-hydroxycarboxylic acids. A convenient method has been developed to synthesize this compound. It is observed that (S)-mandelic acid enhances the fluorescence intensity of the (S,S)-sensor significantly more than (R)-mandelic acid does. The enantioselective fluorescent response is confirmed with the observation of a mirror image relationship for the interaction of (S,S)- and (R,R)-sensors with mandelic acid. The enantioselectivity in fluorescence response [(IS - I0)/(IR - I0) = 2.49] is quite high, which makes the sensor useful for practical application. The fluorescence intensity change of the sensor is found to be linearly related to the enantiomeric composition of mandelic acid. This sensor is potentially useful for the combinatorial search of chiral catalysts for the asymmetric synthesis of α-hydroxycarboxylic acids. Copyright © 2002 American Chemical Society.

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页码：2088 / 2089

页数：2

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