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

doi:10.1002/macp.201500154

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

Research output: Contribution to journal › Article

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 language	English
Pages (from-to)	1850-1855
Number of pages	6
Journal	Macromolecular Chemistry and Physics
Volume	216
Issue number	18
DOIs	https://doi.org/10.1002/macp.201500154
Publication status	Published - 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

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title = "Vanadyl-TrBR4-Catalyzed Oxidative Polymerization of Diphenyl Disulfide",

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.",

keywords = "borates, Lewis acids, oxidative polymerization, poly(1 4-phenylene sulfide), vanadyl complexes",

author = "Fuyuki Aida and Souske Yamaguchi and Yohei Takatori and Kentaro Nagamatsu and Daichi Kiyokawa and Kenichi Oyaizu and Hiroyuki Nishide",

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doi = "10.1002/macp.201500154",

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T1 - Vanadyl-TrBR4-Catalyzed Oxidative Polymerization of Diphenyl Disulfide

AU - Aida, Fuyuki

AU - Yamaguchi, Souske

AU - Takatori, Yohei

AU - Nagamatsu, Kentaro

AU - Kiyokawa, Daichi

AU - Oyaizu, Kenichi

AU - Nishide, Hiroyuki

PY - 2015/9/1

Y1 - 2015/9/1

N2 - 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.

AB - 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.

KW - borates

KW - Lewis acids

KW - oxidative polymerization

KW - poly(1 4-phenylene sulfide)

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10.1002/macp.201500154