Thiazole-induced rigidification in substituted dithieno-tetrathiafulvalene: The effect of planarisation on charge transport properties
journal contributionposted on 16.12.2016, 13:55 by Rupert G.D. Taylor, Joseph Cameron, Iain WrightIain 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.