Thiol-benzoxazine chemistry as a novel Thiol-X reaction for the synthesis of block copolymers

Abdulrahman Musa; Baris Kiskan; Yusuf Yagci

doi:10.1016/j.polymer.2014.06.076

Thiol-benzoxazine chemistry as a novel Thiol-X reaction for the synthesis of block copolymers

Abdulrahman Musa, Baris Kiskan, Yusuf Yagci^*

^*Corresponding author for this work

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

35 Scopus citations

Abstract

A novel synthetic procedure is reported for the preparation of block copolymers by means of successive 1,3-benzoxazine-thiol and Husigen type azide-alkyne coupling methodologies in one-pot and sequential synthesis. The applied 1,3-benzoxazine-thiol process based on catalytic opening of the lateral benzoxazine rings by thiols is proposed as a new thiol-X chemistry. Azide functional poly(methyl acrylate) (PMA-N₃), poly(ethylene glycol) (PEG-N₃) and thiol functional polystyrene (PS-SH) were prepared. The obtained PMA-N₃ or PEG-N₃, PS-SH and propargyl benzoxazine as a click-linker were reacted in sequential or one-pot two step manner to yield desired PS-b-PMA and PS-b-PEG block copolymer. The described thiol-benzoxazine chemistry offers a facile and efficient route to exploring the many possibilities in macromolecular synthesis.

Original language	English
Pages (from-to)	5550-5556
Number of pages	7
Journal	Polymer
Volume	55
Issue number	22
DOIs	https://doi.org/10.1016/j.polymer.2014.06.076
State	Published - 23 Oct 2014
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2014 Elsevier Ltd.

Keywords

Benzoxazine
Ring-opening reaction
Thiol chemistry

ASJC Scopus subject areas

Organic Chemistry
Polymers and Plastics
Materials Chemistry

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10.1016/j.polymer.2014.06.076

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title = "Thiol-benzoxazine chemistry as a novel Thiol-X reaction for the synthesis of block copolymers",

abstract = "A novel synthetic procedure is reported for the preparation of block copolymers by means of successive 1,3-benzoxazine-thiol and Husigen type azide-alkyne coupling methodologies in one-pot and sequential synthesis. The applied 1,3-benzoxazine-thiol process based on catalytic opening of the lateral benzoxazine rings by thiols is proposed as a new thiol-X chemistry. Azide functional poly(methyl acrylate) (PMA-N3), poly(ethylene glycol) (PEG-N3) and thiol functional polystyrene (PS-SH) were prepared. The obtained PMA-N3 or PEG-N3, PS-SH and propargyl benzoxazine as a click-linker were reacted in sequential or one-pot two step manner to yield desired PS-b-PMA and PS-b-PEG block copolymer. The described thiol-benzoxazine chemistry offers a facile and efficient route to exploring the many possibilities in macromolecular synthesis.",

keywords = "Benzoxazine, Ring-opening reaction, Thiol chemistry",

author = "Abdulrahman Musa and Baris Kiskan and Yusuf Yagci",

note = "Publisher Copyright: {\textcopyright} 2014 Elsevier Ltd.",

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doi = "10.1016/j.polymer.2014.06.076",

language = "English",

volume = "55",

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T1 - Thiol-benzoxazine chemistry as a novel Thiol-X reaction for the synthesis of block copolymers

AU - Musa, Abdulrahman

AU - Kiskan, Baris

AU - Yagci, Yusuf

PY - 2014/10/23

Y1 - 2014/10/23

N2 - A novel synthetic procedure is reported for the preparation of block copolymers by means of successive 1,3-benzoxazine-thiol and Husigen type azide-alkyne coupling methodologies in one-pot and sequential synthesis. The applied 1,3-benzoxazine-thiol process based on catalytic opening of the lateral benzoxazine rings by thiols is proposed as a new thiol-X chemistry. Azide functional poly(methyl acrylate) (PMA-N3), poly(ethylene glycol) (PEG-N3) and thiol functional polystyrene (PS-SH) were prepared. The obtained PMA-N3 or PEG-N3, PS-SH and propargyl benzoxazine as a click-linker were reacted in sequential or one-pot two step manner to yield desired PS-b-PMA and PS-b-PEG block copolymer. The described thiol-benzoxazine chemistry offers a facile and efficient route to exploring the many possibilities in macromolecular synthesis.

AB - A novel synthetic procedure is reported for the preparation of block copolymers by means of successive 1,3-benzoxazine-thiol and Husigen type azide-alkyne coupling methodologies in one-pot and sequential synthesis. The applied 1,3-benzoxazine-thiol process based on catalytic opening of the lateral benzoxazine rings by thiols is proposed as a new thiol-X chemistry. Azide functional poly(methyl acrylate) (PMA-N3), poly(ethylene glycol) (PEG-N3) and thiol functional polystyrene (PS-SH) were prepared. The obtained PMA-N3 or PEG-N3, PS-SH and propargyl benzoxazine as a click-linker were reacted in sequential or one-pot two step manner to yield desired PS-b-PMA and PS-b-PEG block copolymer. The described thiol-benzoxazine chemistry offers a facile and efficient route to exploring the many possibilities in macromolecular synthesis.

KW - Benzoxazine

KW - Ring-opening reaction

KW - Thiol chemistry

UR - https://www.scopus.com/pages/publications/84908043757

U2 - 10.1016/j.polymer.2014.06.076

DO - 10.1016/j.polymer.2014.06.076

M3 - Article

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SN - 0032-3861

VL - 55

SP - 5550

EP - 5556

JO - Polymer

JF - Polymer

IS - 22

ER -

Thiol-benzoxazine chemistry as a novel Thiol-X reaction for the synthesis of block copolymers

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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