Vanadyl-TrBR<inf>4</inf>-Catalyzed Oxidative Polymerization of Diphenyl Disulfide

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

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    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)<inf>2</inf>) and triphenylmethylium tetrakis(pentafluorophenyl)borate (TrB(C<inf>6</inf>F<inf>5</inf>)<inf>4</inf>) proceeds the polymerization to give poly(1,4-phenylene sulfide) (PPS) at 100 °C. When triphenylmethylium tetrafluoroborate (TrBF<inf>4</inf>) 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 H<inf>2</inf>O from O<inf>2</inf> and protons that are eliminated from the monomer. Strong-acid-free oxygen-oxidative polymerization of PhSSPh is presented, catalyzed by a vanadyl and TrBR<inf>4</inf> system. TrB(C<inf>6</inf>F<inf>5</inf>)<inf>4</inf> is found to activate VO(acac)<inf>2</inf> at 100 °C and the catalyst gives poly(1,4-phenylene sulfide) (PPS) from PhSSPh. TrBF<inf>4</inf> 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

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    Keywords

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

    ASJC Scopus subject areas

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

    Cite this

    Aida, F., Yamaguchi, S., Takatori, Y., Nagamatsu, K., Kiyokawa, D., Oyaizu, K., & Nishide, H. (2015). Vanadyl-TrBR<inf>4</inf>-Catalyzed Oxidative Polymerization of Diphenyl Disulfide. Macromolecular Chemistry and Physics, 216(18), 1850-1855. https://doi.org/10.1002/macp.201500154