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

Research output: Contribution to journalArticle

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.
LanguageEnglish
Pages1403-1410
Number of pages7
JournalJournal of the Chemical Society, Perkin Transactions 1
Volume1993
Issue number1
DOIs
Publication statusPublished - 7 Jul 1993

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Crystal structure
Derivatives
X rays
tetrathiafulvalene
X ray analysis
Selenium
Sulfur
Dimers
Ether
Anions
Esters
Single crystals

Keywords

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

Cite this

Moore, A.J. ; Bryce, M.R. ; Cooke, G. ; Marshallsay, G.J. ; Skabara, P.J. ; Batsanov, A.S. ; Howard, J.A.K. ; Daley, S.T.A.K. / Chalcogenation of tetrathiafulvalene (TTF): synthesis of alkylthio-TTF and alkylseleno-TTF derivatives and X-ray crystal structure of ethylenediseleno TTF (EDS-TTF). In: Journal of the Chemical Society, Perkin Transactions 1. 1993 ; Vol. 1993, No. 1. pp. 1403-1410.
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Chalcogenation of tetrathiafulvalene (TTF): synthesis of alkylthio-TTF and alkylseleno-TTF derivatives and X-ray crystal structure of ethylenediseleno TTF (EDS-TTF). / Moore, A.J.; Bryce, M.R.; Cooke, G.; Marshallsay, G.J.; Skabara, P.J.; Batsanov, A.S.; Howard, J.A.K.; Daley, S.T.A.K.

In: Journal of the Chemical Society, Perkin Transactions 1, Vol. 1993, No. 1, 07.07.1993, p. 1403-1410.

Research output: Contribution to journalArticle

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AU - Cooke, G.

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AU - Skabara, P.J.

AU - Batsanov, A.S.

AU - Howard, J.A.K.

AU - Daley, S.T.A.K.

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AB - 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.

KW - organic metals

KW - carbon-disulfide

KW - bedt-ttf

KW - salts

KW - substituents

KW - chemistry

KW - precursor

KW - donors

KW - films

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