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Thiazole-induced rigidification in substituted dithieno-tetrathiafulvalene: The effect of planarisation on charge transport properties

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posted on 16.12.2016 by Rupert G.D. Taylor, Joseph Cameron, Iain Wright, Neil Thomson, Olena Avramchenko, Alexander L. Kanibolotsky, Anto R. Inigo, Tell Tuttle, Peter J. Skabara
© 2015 Taylor et al; licensee Beilstein-Institut.Two novel tetrathiafulvalene (TTF) containing compounds 1 and 2 have been synthesised via a four-fold Stille coupling between a tetrabromo-dithienoTTF 5 and stannylated thiophene 6 or thiazole 4. The optical and electrochemical properties of compounds 1 and 2 have been measured by UV-vis spectroscopy and cyclic voltammetry and the results compared with density functional theory (DFT) calculations to confirm the observed properties. Organic field effect transistor (OFET) devices fabricated from 1 and 2 demonstrated that the substitution of thiophene units for thiazoles was found to increase the observed charge transport, which is attributed to induced planarity through S-N interactions of adjacent thiazole nitrogen atoms and TTF sulfur atoms and better packing in the bulk.

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  • Science

Department

  • Chemistry

Published in

Beilstein Journal of Organic Chemistry

Volume

11

Pages

1148 - 1154

Citation

TAYLOR, R.G.D. ...et al., 2015. Thiazole-induced rigidification in substituted dithieno-tetrathiafulvalene: The effect of planarisation on charge transport properties. Beilstein Journal of Organic Chemistry, 11, pp. 1148-1154.

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© The authors. Published by Beilstein-Institut.

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VoR (Version of Record)

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This work is made available according to the conditions of the Creative Commons Attribution 2.0 Unported (CC BY 2.0) licence. Full details of this licence are available at: http://creativecommons.org/licenses/by/2.0/

Publication date

2015

Notes

This is an Open Access Article. It is published by Beilstein-Institut under the Creative Commons Attribution 2.0 Unported Licence (CC BY). Full details of this licence are available at: http://creativecommons.org/licenses/by/2.0/

eISSN

1860-5397

Language

en

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