Design, synthesis, chemical stability, packing, cyclic voltammetry, ionisation potential, and charge transport of [1]benzothieno[3,2-b][1]benzothiophene derivatives

Christian Ruzie, Jolanta Karpinska, Anne Laurent, Lionel Sanguinet, Simon Hunter, Thomas D. Anthopoulos, Vincent Lemaur, Jérôme Cornil, Alan R. Kennedy, Oliver Fenwick, Paolo Samori, Guillaume Schweicher, Basab Chattopadhyay, Yves Henri Geerts

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17 Citations (Scopus)
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Abstract

Five new molecular semiconductors that differ from dioctylbenzothienobenzothiophene, by the introduction of ether or thioether side chains, have been synthesized and obtained in good yields. Their availability in sufficient quantities has allowed investigation of their electrochemical behaviour in solution and their electronic properties in solid state. Both ether and thioether compounds oxidise rather easily in solution, but nevertheless, they exhibit rather high ionisation potentials. This is a consequence of their crystal structure. Dioctylthioetherbenzothienobenzothiophene is rather sensitive to oxidation and degrades easily in close to ambient conditions. Dioctylletherbenzothienobenzothiophene is more stable. Its charge carrier mobility remains however rather moderate, on the order of 0.5 cm2/V.s, whereas that of dioctylbenzothienobenzothiophene reached 4 cm2/V.s, in the same conditions. The difference is explained by intrinsic factors as shown by a theoretical modelling.
Original languageEnglish
JournalJournal of Materials Chemistry. C
Early online date5 May 2016
DOIs
Publication statusE-pub ahead of print - 5 May 2016

Keywords

  • molecular semiconductors
  • dioctylthioetherbenzothienobenzothiophene
  • chemical stability

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