Bis-calix[4]arenes Bridged by an Electroactive Tetrathiafulvalene Unit

Syntheses of the first bis-calixarenes systems bridged by a tetrathiafulvalene (TTF) framework 5a,b have been carried out in good yields through triethyl phosphite-mediated dechalcogenation−dimerizations of the corresponding 1,3-dithiole-2-(thi)ones 3 or 4. X-ray structures of the calix[4]arene−TTF−...

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Bibliographic Details
Published in:Journal of organic chemistry 2005-08, Vol.70 (16), p.6254-6257
Main Authors: Zhao, Bang-Tun, Blesa, María-Jesús, Mercier, Nicolas, Le Derf, Franck, Sallé, Marc
Format: Article
Language:English
Subjects:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemical Sciences
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Material chemistry
Organic chemistry
Preparations and properties
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Summary:Syntheses of the first bis-calixarenes systems bridged by a tetrathiafulvalene (TTF) framework 5a,b have been carried out in good yields through triethyl phosphite-mediated dechalcogenation−dimerizations of the corresponding 1,3-dithiole-2-(thi)ones 3 or 4. X-ray structures of the calix[4]arene−TTF−calix[4]arene assembly 5b and of the calix[4]arene−thione intermediate 3b are analyzed and confirm the cone conformations adopted by the calix[4]arene parts, as it is also observed by 1H NMR analysis of these systems. The solid-state organization in 5b leads to alternate layers of calixarene and TTF units. The cyclic voltammograms of 5a,b show as expected a two-step redox behavior but display a CV deformation for the second redox process.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0505876