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

共 47 条

[1]

Alfonso I, 2000, CHEM-EUR J, V6, P3331, DOI 10.1002/1521-3765(20000915)6:18<3331::AID-CHEM3331>3.0.CO

[2]

2-8

[3]

Alfonso I, 2001, HELV CHIM ACTA, V84, P280, DOI 10.1002/1522-2675(20010228)84:2<280::AID-HLCA280>3.3.CO

[4]

2-F

[5] Chiral mono boronic acid as fluorescent enantioselective sensor for mono α-hydroxyl carboxylic acids [J].

Chi, Lina ;

Zhao, Jianzhang ;

James, Tony D. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (12) :4684-4687

[6] Fluorescent quantum dots with boronic acid substituted viologens to sense glucose in aqueous solution [J].

Cordes, David B. ;

Gamsey, Soya ;

Singaram, Bakthan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (23) :3829-3832

[7] Steady state and time resolved studies on photophysical properties of carbazole and 9-phenyl carbazole molecules and their quenching reactions with suitable electron accepters in the excited electronic states both at the ambient temperature and at 77 K [J].

De, AK ;

Ganguly, T .

JOURNAL OF LUMINESCENCE, 2001, 92 (04) :255-270

[8] Signaling recognition events with fluorescent sensors and switches [J].

de Silva, AP ;

Gunaratne, HQN ;

Gunnlaugsson, T ;

Huxley, AJM ;

McCoy, CP ;

Rademacher, JT ;

Rice, TE .

CHEMICAL REVIEWS, 1997, 97 (05) :1515-1566

[9] Spectral properties of fluorophores combining the boronic acid group with electron donor or withdrawing groups. Implication in the development of fluorescence probes for saccharides [J].

DiCesare, N ;

Lakowicz, JR .

JOURNAL OF PHYSICAL CHEMISTRY A, 2001, 105 (28) :6834-6840

[10] Fluorescent probe for monosaccharides based on a functionalized boron-dipyrromethene with a boronic acid group [J].

DiCesare, N ;

Lakowicz, JR .

TETRAHEDRON LETTERS, 2001, 42 (52) :9105-9108

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