Elsevier

Tetrahedron Letters

Volume 46, Issue 46, 14 November 2005, Pages 7871-7875
Tetrahedron Letters

Probing the conformational changes upon oxidation in cross-conjugated architectures featuring vinylogous TTF units

https://doi.org/10.1016/j.tetlet.2005.09.108Get rights and content

Abstract

We report the synthesis and electropolymerisation of 1,3,5-tris(1,3-dithiole-2-ylidenephenylene)benzene 4. The resulting polymer features extended tetrathiafulvalene (TTF) units and can be considered as a cross-conjugated, cross-linked structure. Upon p-doping, electrochemical and UV–vis spectroelectrochemical experiments indicate that the polymer undergoes a unique conformational change within the dendralene unit from one definitive orthogonal arrangement to another.

Graphical abstract

We report the synthesis and electropolymerisation of 1,3,5-tris(1,3-dithiole-2-ylidenephenylene)benzene 4. The resulting polymer features extended tetrathiafulvalene (TTF) units and can be considered as a cross-conjugated, cross-linked structure. Upon p-doping, electrochemical and UV–vis spectroelectrochemical experiments indicate that the polymer undergoes a unique conformational change within the dendralene unit from one definitive orthogonal arrangement to another.

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Acknowledgement

Financial support from MEC-FEDER (BQU2002-00219) and Gobierno de Aragón (E39) is gratefully acknowledged.

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New address: Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Galasgow G1 1XL, UK.

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