Chalcogenation of tetrathiafulvalene (TTF): synthesis of alkylthio-TTF and alkylseleno-TTF derivatives and X-ray crystal structure of ethylenediseleno TTF (EDS-TTF)

A.J. Moore, M.R. Bryce, G. Cooke, G.J. Marshallsay, P.J. Skabara, A.S. Batsanov, J.A.K. Howard, S.T.A.K. Daley

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23 Citations (Scopus)

Abstract

The reaction of mono-lithiated tetrathiafulvalene (TTF) with elemental sulfur or elemental selenium at -78-degrees-C yields the transient species TTF-S- Li+ and TTF-Se- Li+, respectively, which have been trapped with a range of alkyl halides to yield new alkylthio- and alkylseleno-TTF derivatives. Reaction of the TTF-thiolate anion with 2-bromoethanol yields 4-(2-hydroxyethylthio)tetrathiafulvalene which is a particularly versatile building block for the synthesis of a range of new mono-functionalised TTF derivatives containing ether, ester, acrylate, urethane and vinylthio groups in the side chain. One-pot syntheses of ethylenedithio-TTF (EDT-TTF) and ethylenediseleno-TTF (EDS-TTF) from TTF are reported. The structure of EDS-TTF has been determined by single crystal X-ray analysis which reveals dimers with molecular planes orthogonal to each other.
Original languageEnglish
Pages (from-to)1403-1410
Number of pages7
JournalJournal of the Chemical Society, Perkin Transactions 1
Volume1993
Issue number1
DOIs
Publication statusPublished - 7 Jul 1993

Keywords

  • organic metals
  • carbon-disulfide
  • bedt-ttf
  • salts
  • substituents
  • chemistry
  • precursor
  • donors
  • films

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