Polymerization of methyl phenyl sulfoxide under acidic conditions

Synthesis and X-ray structure analysis of a phenylene sulfonium polymer

Kenji Miyatake, Kenichi Oyaizu, Yukio Nishimura, Eishun Tsuchida

    Research output: Contribution to journalArticle

    15 Citations (Scopus)

    Abstract

    Methyl phenyl sulfoxide was found to undergo self-polycondensation in triflic acid in the presence of diphenylamine to produce poly(methylsulfonio-1,4-phenylene triflate). Diphenylamine formed a charge-transfer (CT) complex with the hydroxy methyl phenyl sulfonium cation produced by the protonation of the sulfoxide, facilitating the electrophilic substitution reaction of the sulfonium cation onto the carbon atom of the terminal phenyl ring. The obtained polymer is a highly crystalline material whose structure was determined by X-ray analysis using the typical geometric parameters of the sulfoniophenylene dimer and trimer model compounds. The orthorhombic unit cell of the polymer (a = 10.875 angstroms, b = 10.449 angstroms, and c = 18.629 angstroms) contains eight monomeric units. The space group is Pbcn (#60). Two molecular chains along the c axis pass through the unit cell, one through the corner and the other through the center. The crystal structure of the polymer not only revealed a structural relevance to those of oxy- and thiophenylene polymers but also provided support for CT complex formation between the polymer and diphenylamine.

    Original languageEnglish
    Pages (from-to)1172-1179
    Number of pages8
    JournalMacromolecules
    Volume34
    Issue number5
    DOIs
    Publication statusPublished - 2001 Feb 27

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    Diphenylamine
    Polymers
    Polymerization
    X rays
    sulfoxide
    Cations
    Charge transfer
    Positive ions
    Protonation
    X ray analysis
    Polycondensation
    Dimers
    Substitution reactions
    Carbon
    Crystal structure
    methyl phenyl sulfoxide
    Crystalline materials
    Atoms
    Acids

    ASJC Scopus subject areas

    • Materials Chemistry

    Cite this

    Polymerization of methyl phenyl sulfoxide under acidic conditions : Synthesis and X-ray structure analysis of a phenylene sulfonium polymer. / Miyatake, Kenji; Oyaizu, Kenichi; Nishimura, Yukio; Tsuchida, Eishun.

    In: Macromolecules, Vol. 34, No. 5, 27.02.2001, p. 1172-1179.

    Research output: Contribution to journalArticle

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