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

Taylor, Rupert G. D. and Cameron, Joseph and Wright, Iain A. and Thomson, Neil and Avramchenko, Olena and Kanibolotsky, Alexander L. and Inigo, Anto R. and Tuttle, Tell and Skabara, Peter J. (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. ISSN 1860-5397

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    Abstract

    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.

    Author(s):Taylor, Rupert G. D. ORCID: https://orcid.org/0000-0002-0841-8298, Cameron, Joseph ORCID: https://orcid.org/0000-0001-8622-8353, Wright, Iain A., Thomson, Neil, Avramchenko, Olena ORCID: https://orcid.org/0000-0002-4354-8549, Kanibolotsky, Alexander L., Inigo, Anto R., Tuttle, Tell and Skabara, Peter J. ORCID: https://orcid.org/0000-0001-7319-0464
    Item type:Article
    ID code:54067
    Keywords:non-covalent interactions, organic field effect transistor (ofet), organic semiconductors, tetrathiafulvalene, thiazole, Chemistry, Organic Chemistry
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Technology and Innovation Centre > Photonics
    Depositing user: Pure Administrator
    Date deposited:25 Aug 2015 13:48
    Last modified:21 Jun 2019 02:55
    Related URLs:
    URI:https://strathprints.strath.ac.uk/id/eprint/54067
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