Enantioselective Sensing by Luminescence

被引:96
作者
Accetta, Alessandro [1 ]
Corradini, Roberto [1 ]
Marchelli, Rosangela [1 ]
机构
[1] Univ Parma, Dipartimento Chim Organ & Ind, I-43124 Parma, Italy
来源
LUMINESCENCE APPLIED IN SENSOR SCIENCE | 2011年 / 300卷
关键词
Chiral analysis; Enantiomeric recognition; Fluorescent sensors; Luminescence; INDICATOR-DISPLACEMENT ASSAYS; CHIRAL LANTHANIDE COMPLEXES; TRANSITION-METAL CATALYSIS; AMINO-ACID DERIVATIVES; FLUORESCENT RECOGNITION; MOLECULAR RECOGNITION; ENANTIOMERIC EXCESS; COPPER(II) COMPLEX; CHOLIC-ACID; PHOSPHORESCENT ANALYTES;
D O I
10.1007/128_2010_95
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Enantiomeric analysis is one of the crucial points for the sensor technology, due to the increasing importance that enantiomerically pure compounds and drugs have in pharmaceutic and agrochemical applications. Enantiomeric luminescent sensors give different responses by interaction or reaction with chiral molecules, allowing one to assess their optical purity by spectroscopic measurements. Moreover, chemosensors have been developed to perform enantiomeric analysis of both luminescent and non-luminescent organic compounds. In the present chapter we focus on the recent advances in the sensing of chiral molecules by luminescent sensory systems, with the aim of outlining different mechanisms: fluorescence quenching by metal complexes, photoinduced electron transfer (PET) quenching, fluorescence enhancement by PET inhibition, analyte induced sensor conformational changes, modulation of excimer and exciplex formation, and aggregation induced emission enhancement (AIEE). Recent advances in the use of more elaborate techniques such as anisotropy measurements, gated detection, circularly polarized luminescence (CPL) and perspectives in the field are also discussed. Emphasis is given to the methods which have provided high enantioselectivity and which are amenable to fast screening procedures.
引用
收藏
页码:175 / 216
页数:42
相关论文
共 154 条
[41]   FLUORESCENT SENSORS OF MOLECULAR RECOGNITION - MODIFIED CYCLODEXTRINS CAPABLE OF EXHIBITING GUEST-RESPONSIVE TWISTED INTRAMOLECULAR CHARGE-TRANSFER FLUORESCENCE [J].
HAMASAKI, K ;
IKEDA, H ;
NAKAMURA, A ;
UENO, A ;
TODA, F ;
SUZUKI, I ;
OSA, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (12) :5035-5040
[42]   3,6-Disubstituted Carbazole-Based Bisboronic Acids with Unusual Fluorescence Transduction as Enantioselective Fluorescent Chemosensors for Tartaric Acid [J].
Han, Feng ;
Chi, Lina ;
Liang, Xiaofen ;
Ji, Shaomin ;
Liu, Shasha ;
Zhou, Fuke ;
Wu, Yubo ;
Han, Keli ;
Zhao, Jianzhang ;
James, Tony D. .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (03) :1333-1336
[43]   Algorithms for the determination of binding constants and enantiomeric excess in complex host : guest equilibria using optical measurements [J].
Hargrove, Amanda E. ;
Zhong, Zhenlin ;
Sessler, Jonathan L. ;
Anslyn, Eric V. .
NEW JOURNAL OF CHEMISTRY, 2010, 34 (02) :348-354
[44]   Highly enantioselective fluorescent sensor for chiral recognition of amino acid derivatives [J].
He, Xuan ;
Cui, Xin ;
Li, Maosi ;
Lin, Lili ;
Liu, Xiaohua ;
Feng, Xiaoming .
TETRAHEDRON LETTERS, 2009, 50 (42) :5853-5856
[45]   An enantioselective fluorescence sensor for glucose based on a cyclic tetrapeptide containing two boronic acid binding sites [J].
Heinrichs, Guido ;
Schellentraeger, Marc ;
Kubik, Stefan .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (18) :4177-4186
[46]   Chirality-sensing supramolecular systems [J].
Hembury, Guy A. ;
Borovkov, Victor V. ;
Inoue, Yoshihisa .
CHEMICAL REVIEWS, 2008, 108 (01) :1-73
[47]   Synthesis and enantioselective recognition of an (S)-BINOL-based colorimetric chemosensor for mandelate anions [J].
Hu, Chenguang ;
He, Yongbing ;
Chen, Zhihong ;
Huang, Xiaohuan .
TETRAHEDRON-ASYMMETRY, 2009, 20 (01) :104-110
[48]   Skeleton-selective fluorescent chemosensor based on cyclodextrin bearing a 4-amino-7-nitrobenz-2-oxa-1,3-diazole moiety [J].
Ikeda, H ;
Murayama, T ;
Ueno, A .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (23) :4262-4267
[49]   Chiral recognition by fluorescent chemosensors based on N-dansyl-amino acid-modified cyclodextrins [J].
Ikeda, Hiroshi ;
Li, Qun ;
Ueno, Akihiko .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (20) :5420-5423
[50]   6-DEOXY-6-N-HISTAMINO-BETA-CYCLODEXTRIN COPPER(II) COMPLEX, A NEW ENANTIOSELECTIVE RECEPTOR FOR AROMATIC-AMINO-ACIDS [J].
IMPELLIZZERI, G ;
MACCARRONE, G ;
RIZZARELLI, E ;
VECCHIO, G ;
CORRADINI, R ;
MARCHELLI, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (10) :1348-1349