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

Autor: Rupert G. D. Taylor, Joseph Cameron, Iain A. Wright, Neil Thomson, Olena Avramchenko, Alexander L. Kanibolotsky, Anto R. Inigo, Tell Tuttle, Peter J. Skabara
Jazyk: angličtina
Rok vydání: 2015
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 11, Iss 1, Pp 1148-1154 (2015)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.11.129
Popis: 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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