Cyclic arylene sulfides: A novel synthesis and ring-opening polymerization

Eishun Tsuchida, Kenji Miyatake, Kimihisa Yamamoto, Allan S. Hay

Research output: Contribution to journalArticle

35 Citations (Scopus)

Abstract

Oxidative polymerization of aryl disulfides has been carried out under high dilution conditions for the preparation of cyclic arylene sulfides. The readily available diphenyl disulfide and dichloro disulfide with diphenyl sulfide, diphenyl ether, or p-xylene are useful monomers for the synthesis of the corresponding cyclic oligo(thio arylene)s in ∼ 69% yield. The cyclization of dichloro disulfide with p-xylene gives cyclic oligo(thio-2,5-dimethyl-1,4-phenylene) (3c) bearing a disulfide bond with the repeating units ranging from 3 to 10. The free radical ring-opening polymerization of the cyclics leads to the formation of linear poly(thio arylene)s. The obtained poly(thio-2,5-dimethyl-1,4-phenylene) (6c) has a melting temperature of 354 °C, which is 71 °C higher than that of the unsubstituted poly(thio phenylene).

Original languageEnglish
Pages (from-to)6469-6475
Number of pages7
JournalMacromolecules
Volume31
Issue number19
DOIs
Publication statusPublished - 1998 Sep 22

ASJC Scopus subject areas

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

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