3,6-Disubstituted Carbazole-Based Bisboronic Acids with Unusual Fluorescence Transduction as Enantioselective Fluorescent Chemosensors for Tartaric Acid

被引：101

作者：

Han, Feng ^{[1
]}

Chi, Lina ^{[1
]}

Liang, Xiaofen ^{[1
]}

Ji, Shaomin ^{[1
]}

Liu, Shasha ^{[2
]}

Zhou, Fuke ^{[1
]}

Wu, Yubo ^{[1
]}

Han, Keli ^{[3
]}

Zhao, Jianzhang ^{[1
]}

James, Tony D. ^{[4
]}

机构：

[1] Dalian Univ Technol, Sch Chem Engn, State Key Lab Fine Chem, Dalian 116012, Peoples R China

[2] Dalian Univ Technol, Sch Phys & Optoelect Technol, Dalian 116012, Peoples R China

[3] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China

[4] Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 03期

关键词：

CHIRAL-ANION RECOGNITION; TEACHING OLD INDICATORS; BORONIC ACID; ENANTIOMERIC EXCESS; REPORTER COMPOUNDS; SUGAR ACIDS; SENSORS; MOLECULES; SACCHARIDES; RECEPTORS;

D O I：

10.1021/jo8025669

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Carbazole-based bisboronic acids were found to be enantioselective fluorescent sensors for tartaric acid. The fluorescence response toward the enantiomers of tartaric acid at neutral pH displayed enhancement/diminishment. The sensor displays an unusual fluorescence intensity-pH relationship with diminished emission at acidic pH but. enhanced emission at basic pH. Photoinduced electron transfer (PET) from the fluorophore to the protonated amine/phenylboronic acid unit is proposed to be responsible for this effect, which is rationalized by density functional theory (DFT) calculations.

引用

页码：1333 / 1336

页数：4

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