Vanadyl-TrBR4-Catalyzed Oxidative Polymerization of Diphenyl Disulfide

Fuyuki Aida, Souske Yamaguchi, Yohei Takatori, Kentaro Nagamatsu, Daichi Kiyokawa, Kenichi Oyaizu, Hiroyuki Nishide

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

A newly established catalyst system for oxygen-oxidative polymerization of diphenyl disulfide is reported. Combination of vanadyl compounds (e.g., VO(acac)2) and triphenylmethylium tetrakis(pentafluorophenyl)borate (TrB(C6F5)4) proceeds the polymerization to give poly(1,4-phenylene sulfide) (PPS) at 100 °C. When triphenylmethylium tetrafluoroborate (TrBF4) is applied with vanadyl tetraphenylporphyrin (VO(TPP)) or N,N′-(ethylenebis(salicylideneaminato))oxovanadium (VO(salen)), PPS is also given via polymerization under conditions near 160 °C. Combination of the vanadyl complex and the borate affords the first protic-acid-free catalytic system for the polymerization of the disulfide, suggesting the overall reaction to produce PPS and H2O from O2 and protons that are eliminated from the monomer. Strong-acid-free oxygen-oxidative polymerization of PhSSPh is presented, catalyzed by a vanadyl and TrBR4 system. TrB(C6F5)4 is found to activate VO(acac)2 at 100 °C and the catalyst gives poly(1,4-phenylene sulfide) (PPS) from PhSSPh. TrBF4 has stronger nucleophilicity, but is found to activate VO(salen) and VO(TPP) at 160 °C for preparing PPS.

Original languageEnglish
Pages (from-to)1850-1855
Number of pages6
JournalMacromolecular Chemistry and Physics
Volume216
Issue number18
DOIs
Publication statusPublished - 2015 Sep 1

Keywords

  • Lewis acids
  • borates
  • oxidative polymerization
  • poly(1 4-phenylene sulfide)
  • vanadyl complexes

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Polymers and Plastics
  • Materials Chemistry

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  • Cite this

    Aida, F., Yamaguchi, S., Takatori, Y., Nagamatsu, K., Kiyokawa, D., Oyaizu, K., & Nishide, H. (2015). Vanadyl-TrBR4-Catalyzed Oxidative Polymerization of Diphenyl Disulfide. Macromolecular Chemistry and Physics, 216(18), 1850-1855. https://doi.org/10.1002/macp.201500154