A highly enantioselective chiral Schiff-base fluorescent sensor for mandelic acid

被引：27

作者：

Dhara, Koushik ^{[1
]}

Sarkar, Krishanu ^{[2
,3
]}

Roy, Partha ^{[1
]}

Nandi, Mahasweta ^{[2
,3
]}

Bhaumik, Asim ^{[2
,3
]}

Banerjee, Pradyot ^{[1
]}

机构：

[1] Indian Assoc Cultivat Sci, Dept Inorgan Chem, Kolkata 700032, India

[2] Indian Assoc Cultivat Sci, Dept Mat Sci, Kolkata 700032, India

[3] Indian Assoc Cultivat Sci, Ctr Adv Mat, Kolkata 700032, India

来源：

TETRAHEDRON | 2008年 / 64卷 / 14期

关键词：

chiral Schiff-base; alpha-hydroxycarboxylic acid; enantioselective; fluorescent sensor;

D O I：

10.1016/j.tet.2008.01.099

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A chiral Schiff-base compound, 4-methyl-2,6-bis-[(2-hydroxy-1-phenylethylimino)methyl]phenol, is found to act as highly enantioselective fluorescent agent for alpha-hydroxycarboxylic acid, e.g., mandelic acid. It is observed that, within a certain concentration range, one enantiomer of the chiral acid can increase the fluorescence intensity of the Schiff-base compound 122-fold while the other enantiomer enhances the intensity only 42-fold. Such highly enantioselective responses towards the chiral acid make the unusual Schiff-base compound attractive as a fluorescent sensor for determining the enantiomeric composition of alpha-hydroxycarboxylic acids. (c) 2008 Elsevier Ltd. All rights reserved.

引用

页码：3153 / 3159

页数：7

共 63 条

[11]

Ding KL, 1999, ANGEW CHEM INT EDIT, V38, P497, DOI 10.1002/(SICI)1521-3773(19990215)38:4<497::AID-ANIE497>3.0.CO

[12]

2-G

[13] ION-RESPONSIVE FLUORESCENT COMPOUNDS .1. EFFECT OF CATION BINDING ON PHOTOPHYSICAL PROPERTIES OF A BENZOXAZINONE DERIVATIVE LINKED TO MONOAZA-15-CROWN-5 [J].

FERYFORGUES, S ;

LEBRIS, MT ;

GUETTE, JP ;

VALEUR, B .

JOURNAL OF PHYSICAL CHEMISTRY, 1988, 92 (22) :6233-6237

[14] Emerging methods for the rapid determination of enantiomeric excess [J].

Finn, MG .

CHIRALITY, 2002, 14 (07) :534-540

[15]

Fox M. A., 1988, PHOTOINDUCED ELECT T

[16] THE SYNTHESIS, REDOX PROPERTIES, AND LIGAND-BINDING OF HETEROBINUCLEAR TRANSITION-METAL MACROCYCLIC LIGAND COMPLEXES - MEASUREMENT OF AN APPARENT DELOCALIZATION ENERGY IN A MIXED-VALENT CUICUII COMPLEX [J].

GAGNE, RR ;

SPIRO, CL ;

SMITH, TJ ;

HAMANN, CA ;

THIES, WR ;

SHIEMKE, AK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (14) :4073-4081

[17]

Guo JH, 1999, ANGEW CHEM INT EDIT, V38, P1755, DOI 10.1002/(SICI)1521-3773(19990614)38:12<1755::AID-ANIE1755>3.0.CO

[18]

2-Q

[19]

Hanessian S., 1983, TOTAL SYNTHESIS NATU

[20] Pseudo-allosteric recognition of mandelic acid with an enantioselective coordination complex [J].

Heo, J ;

Mirkin, CA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (06) :941-944

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