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

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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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ASJC Scopus subject areas

  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry
  • Materials Chemistry

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