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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. and Bryce, M.R. and Cooke, G. and Marshallsay, G.J. and Skabara, P.J. and Batsanov, A.S. and Howard, J.A.K. and Daley, S.T.A.K. (1993) Chalcogenation of tetrathiafulvalene (TTF): synthesis of alkylthio-TTF and alkylseleno-TTF derivatives and X-ray crystal structure of ethylenediseleno TTF (EDS-TTF). Journal of the Chemical Society, Perkin Transactions 1, 1993 (1). pp. 1403-1410. ISSN 1472-7781

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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.

Item type: Article
ID code: 685
Keywords: organic metals, carbon-disulfide, bedt-ttf, salts, substituents, chemistry, precursor, donors, films, Chemistry, Chemistry(all)
Subjects: Science > Chemistry
Department: Faculty of Science > Pure and Applied Chemistry
Related URLs:
Depositing user: Mr Derek Boyle
Date Deposited: 31 Mar 2006
Last modified: 04 Sep 2014 09:54
URI: http://strathprints.strath.ac.uk/id/eprint/685

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