A combined substituent and supramolecular approach for improving the electron donor properties of 1,3-dithiole-2-thione derivatives

T. Khan, J.J.W. McDouall, E.J.L. McInnes, P.J. Skabara, P. Frere, S.J. Coles, M.B. Hursthouse

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

A series of symmetrical 1,3-dithiole-2-thiones and -ones have been prepared via double lithiation of vinylene trithiocarbonate followed by trapping of the dianions with aryl carbaldehydes. The resulting diols are oxidised in high yield and the corresponding diketones are converted to thiophenes and furans using P2S5-NaHCO3 and P(OEt)(3), respectively. The majority of triaryl compounds undergo two reversible oxidation processes in the range 10.86 to 11.57 V (vs. Ag/AgCl). The charge-transfer complex (8c)(2).TCNQ forms mixed donor-acceptor stacks. EPR spectroscopy confirms the presence of an open shell species, but the material is an electrical insulator. Reaction of 8c with diiodine forms a charge transfer complex with a conductivity of 1.2x10(-4) S cm(-1).
Original languageEnglish
Pages (from-to)2490-2498
Number of pages8
JournalJournal of Materials Chemistry
Volume13
Issue number10
DOIs
Publication statusPublished - 2003

Fingerprint

Thiones
Charge transfer
Furans
Derivatives
Thiophenes
Electrons
Thiophene
Paramagnetic resonance
Spectroscopy
Oxidation
trithiocarbonic acid
tetracyanoquinodimethane

Keywords

  • charge-transfer
  • dihalogens
  • absorption
  • chemistry
  • complexes

Cite this

Khan, T., McDouall, J. J. W., McInnes, E. J. L., Skabara, P. J., Frere, P., Coles, S. J., & Hursthouse, M. B. (2003). A combined substituent and supramolecular approach for improving the electron donor properties of 1,3-dithiole-2-thione derivatives. Journal of Materials Chemistry, 13(10), 2490-2498. https://doi.org/10.1039/b307025e
Khan, T. ; McDouall, J.J.W. ; McInnes, E.J.L. ; Skabara, P.J. ; Frere, P. ; Coles, S.J. ; Hursthouse, M.B. / A combined substituent and supramolecular approach for improving the electron donor properties of 1,3-dithiole-2-thione derivatives. In: Journal of Materials Chemistry. 2003 ; Vol. 13, No. 10. pp. 2490-2498.
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Khan, T, McDouall, JJW, McInnes, EJL, Skabara, PJ, Frere, P, Coles, SJ & Hursthouse, MB 2003, 'A combined substituent and supramolecular approach for improving the electron donor properties of 1,3-dithiole-2-thione derivatives', Journal of Materials Chemistry, vol. 13, no. 10, pp. 2490-2498. https://doi.org/10.1039/b307025e

A combined substituent and supramolecular approach for improving the electron donor properties of 1,3-dithiole-2-thione derivatives. / Khan, T.; McDouall, J.J.W.; McInnes, E.J.L.; Skabara, P.J.; Frere, P.; Coles, S.J.; Hursthouse, M.B.

In: Journal of Materials Chemistry, Vol. 13, No. 10, 2003, p. 2490-2498.

Research output: Contribution to journalArticle

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AU - Khan, T.

AU - McDouall, J.J.W.

AU - McInnes, E.J.L.

AU - Skabara, P.J.

AU - Frere, P.

AU - Coles, S.J.

AU - Hursthouse, M.B.

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