The synthesis, redox properties and X-ray crystal structures of two new tetrathiafulvalene-thiophene donors

P.J. Skabara, K. Mullen, M.R. Bryce, J.A.K. Howard, A.S. Batsanov

Research output: Contribution to journalArticle

31 Citations (Scopus)

Abstract

The functionalisation of tetrathiafulvalene with thiophene units is reported via the synthesis of two multiredox compounds 4 and 5. The two molecules represent a fused structure (4) and a TTF-thiophene system directly linked by a single bond (5); both compounds are endowed with 'free' 2,5-positions within the thiophene ring, making them accessible to polymerisation reactions. The solution electrochemistry of 4 and 5 reveals the redox properties of the two components: a three-stage oxidation process is seen in each case. Charge-transfer complexes have been prepared, using TCNQ or TCNQF(4) as the electron acceptor, with conductivities in the range of 10(-4) to 0.22 S cm(-1). Compounds 4 and 5 have been studied by X-ray crystallography; the former exhibits kappa-packing whilst the latter shows a high degree of conjugation between the two donor moieties.
Original languageEnglish
Pages (from-to)1719-1724
Number of pages5
JournalJournal of Materials Chemistry
Volume8
Issue number8
DOIs
Publication statusPublished - Aug 1998

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Thiophenes
Thiophene
Crystal structure
X rays
X ray crystallography
Electrochemistry
Charge transfer
Polymerization
Oxidation
Molecules
Electrons
Oxidation-Reduction
tetrathiafulvalene

Keywords

  • electron-donor
  • conducting polymers
  • charge-transfer
  • organic metals
  • ttf
  • derivatives
  • chemistry
  • electropolymerization
  • polythiophenes
  • substituents

Cite this

Skabara, P.J. ; Mullen, K. ; Bryce, M.R. ; Howard, J.A.K. ; Batsanov, A.S. / The synthesis, redox properties and X-ray crystal structures of two new tetrathiafulvalene-thiophene donors. In: Journal of Materials Chemistry. 1998 ; Vol. 8, No. 8. pp. 1719-1724.
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The synthesis, redox properties and X-ray crystal structures of two new tetrathiafulvalene-thiophene donors. / Skabara, P.J.; Mullen, K.; Bryce, M.R.; Howard, J.A.K.; Batsanov, A.S.

In: Journal of Materials Chemistry, Vol. 8, No. 8, 08.1998, p. 1719-1724.

Research output: Contribution to journalArticle

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AU - Batsanov, A.S.

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