Phenylboronic acid-functionalized TTFAQ: modular synthesis and electrochemical recognition for saccharides

被引：31

作者：

Shao, Min ^{[1
]}

Zhao, Yuming ^{[1
]}

机构：

[1] Mem Univ Newfoundland, Dept Chem, St John, NF A1B 3X7, Canada

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 18期

基金：

加拿大自然科学与工程研究理事会;

关键词：

Boronic acid; Tetrathiafulvalene; Click reaction; Saccharide sensor; Electrochemistry; TETRATHIAFULVALENE-ANTHRACENE DYAD; BORONIC ACID; CLICK-CHEMISTRY; SENSORS; DERIVATIVES; BINDING;

D O I：

10.1016/j.tetlet.2010.02.171

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A phenylboronic acid-functionalized pi-extended tetrathiafulvalene (TLFAQ) derivative was prepared through an efficient Cu-catalyzed alkyne-azide [3+2] cycloaddition reaction (click reaction). This boronic acid-TTFAQ hybrid system shows different electrochemical redox behavior upon titration with various saccharides in DMSO/H2O at pH 8.75, suggesting potential use in saccharide sensing and recognition. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：2508 / 2511

页数：4

共 33 条

[1] A modular electrochemical sensor for saccharides [J].

Arimori, S ;

Ushiroda, S ;

Peter, LM ;

Jenkins, ATA ;

James, TD .

CHEMICAL COMMUNICATIONS, 2002, (20) :2368-2369

[2] Modular fluorescence sensors for saccharides [J].

Arimori, S ;

Bell, ML ;

Oh, CS ;

Frimat, KA ;

James, TD .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (06) :803-808

[3] Fluorescent internal charge transfer (ICT) saccharide sensor [J].

Arimori, S ;

Bosch, LI ;

Ward, CJ ;

James, TD .

TETRAHEDRON LETTERS, 2001, 42 (27) :4553-4555

[4] Tetrathiafulvalenes, oligoacenenes, and their buckminsterfullerene derivatives: The brick and mortar of organic electronics [J].

Bendikov, M ;

Wudl, F ;

Perepichka, DF .

CHEMICAL REVIEWS, 2004, 104 (11) :4891-4945

[5] CuI-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective [J].

Bock, VD ;

Hiemstra, H ;

van Maarseveen, JH .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (01) :51-68

[6]

Bryce MR, 1999, ADV MATER, V11, P11, DOI 10.1002/(SICI)1521-4095(199901)11:1<11::AID-ADMA11>3.0.CO

[7]

2-3

[8] Fluorescent chemosensors for carbohydrates: A decade's worth of bright spies for saccharides in review [J].

Cao, HS ;

Heagy, MD .

JOURNAL OF FLUORESCENCE, 2004, 14 (05) :569-584

[9] Monoboronic acid sensor that displays anomalous fluorescence sensitivity to glucose [J].

Cao, HS ;

Diaz, DI ;

DiCesare, N ;

Lakowicz, JR ;

Heagy, MD .

ORGANIC LETTERS, 2002, 4 (09) :1503-1505

[10]

Chen G., 2007, ASIAN CHEM LETT, V11, P185

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