Carboxylic acid derivatives of tetrathiafulvalene: key intermediates for the synthesis of redox-active calixarene-based anion receptors

被引:39
作者
Zhao, Bang-Tun [1 ]
Blesa, Maria-Jesus [1 ]
Le Derf, Franck [1 ]
Canevet, David [1 ]
Benhaoua, Chahrazed [1 ]
Mazari, Miloud [1 ]
Allain, Magali [1 ]
Salle, Marc [1 ]
机构
[1] Univ Angers, CNRS 6200, Lab Chim Ingn Mol Mat Angers, UMR, F-49045 Angers, France
关键词
tetrathiafulvalene; calixarene; X-ray structure; anion receptor; cyclic voltammetry;
D O I
10.1016/j.tet.2007.06.119
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of calixarene-TTF (TTF=tetrathiafulvalene) receptors incorporating amide binding units for anion recognition have been synthesized and characterized. For this purpose, two synthetically versatile new TTF carboxylic acid derivatives were prepared and characterized by X-ray diffraction, these structures demonstrating the critical role of the carboxylic function in the solid-state organization. Some of the calixarene-amide-TTF assemblies exhibit strong binding of various anions, as shown by H-1 NMR titration studies, and one receptor is able to electrochemically respond in the presence of H2PO4-. C6H5CO2- or CH3CO2- anion. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:10768 / 10777
页数:10
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