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

doi:10.1039/b307025e

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

Pure And Applied Chemistry

Research output: Contribution to journal › Article › peer-review

17 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 language	English
Pages (from-to)	2490-2498
Number of pages	8
Journal	Journal of Materials Chemistry
Volume	13
Issue number	10
DOIs	https://doi.org/10.1039/b307025e
Publication status	Published - 2003

Keywords

charge-transfer
dihalogens
absorption
chemistry
complexes

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

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).",

keywords = "charge-transfer, dihalogens, absorption, chemistry, complexes",

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

year = "2003",

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language = "English",

volume = "13",

pages = "2490--2498",

journal = "Journal of Materials Chemistry ",

issn = "0959-9428",

publisher = "Royal Society of Chemistry",

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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 journal › Article › peer-review

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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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