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

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

^*Corresponding author for this work

School of Advanced Science and Engineering

Research output: Contribution to journal › Article › peer-review

6 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 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 Sept 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

Access to Document

10.1002/macp.201500154

Cite this

@article{8f97ff4614484b668d620818e4d97a64,

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 = "Lewis acids, borates, 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",

note = "Publisher Copyright: {\textcopyright} 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

year = "2015",

month = sep,

day = "1",

doi = "10.1002/macp.201500154",

language = "English",

volume = "216",

pages = "1850--1855",

journal = "Macromolecular Chemistry and Physics",

issn = "1022-1352",

publisher = "Wiley-VCH Verlag",

number = "18",

}

TY - JOUR

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 - Lewis acids

KW - borates

KW - oxidative polymerization

KW - poly(1 4-phenylene sulfide)

KW - vanadyl complexes

UR - http://www.scopus.com/inward/record.url?scp=84941791691&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84941791691&partnerID=8YFLogxK

U2 - 10.1002/macp.201500154

DO - 10.1002/macp.201500154

M3 - Article

AN - SCOPUS:84941791691

SN - 1022-1352

VL - 216

SP - 1850

EP - 1855

JO - Macromolecular Chemistry and Physics

JF - Macromolecular Chemistry and Physics

IS - 18

ER -