Elsevier

Tetrahedron Letters

Volume 54, Issue 35, 28 August 2013, Pages 4666-4669
Tetrahedron Letters

Bromophenyl substituted dithiafulvenes and tetrathiafulvalene vinylogues: synthesis, structure, and electronic properties

https://doi.org/10.1016/j.tetlet.2013.06.077Get rights and content

Abstract

Bis(bromophenyl) substituted tetrathiafulvalene vinylogues (TTFVs) were prepared via oxidative dimerization reactions of corresponding bromophenyl substituted dithiafulvene precursors. The synthesis of ortho-bromophenyl TTFVs led to the formation of an unexpected bis-spiro product, the structure of which was clearly elucidated by single crystal X-ray crystallography. Electronic and redox properties of the bromophenyl substituted dithiafulvenes, TTFV derivatives, and the related bis-spiro compound were investigated by UV–vis spectroscopic and cyclic voltammetric analyses. Detailed structure–property relationships have been discussed.

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Acknowledgments

We thank NSERC, CFI, and Memorial University for funding support.

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