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

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

doi:10.1021/ma980312a

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

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

^*Corresponding author for this work

Graduate School of Advanced Science and Engineering

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

37 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 language	English
Pages (from-to)	6469-6475
Number of pages	7
Journal	Macromolecules
Volume	31
Issue number	19
DOIs	https://doi.org/10.1021/ma980312a
Publication status	Published - 1998 Sept 22

ASJC Scopus subject areas

Organic Chemistry
Polymers and Plastics
Inorganic Chemistry
Materials Chemistry

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title = "Cyclic arylene sulfides: A novel synthesis and ring-opening polymerization",

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).",

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T1 - Cyclic arylene sulfides

T2 - A novel synthesis and ring-opening polymerization

AU - Tsuchida, Eishun

AU - Miyatake, Kenji

AU - Yamamoto, Kimihisa

AU - Hay, Allan S.

PY - 1998/9/22

Y1 - 1998/9/22

N2 - 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).

AB - 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).

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JF - Macromolecules

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ER -

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

Abstract

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