Orthogonal multifunctionalization of aliphatic polycarbonate via sequential Michael addition and radical-thiol-ene click reactions

Bilal Bugra Uysal; Ufuk Saim Gunay; Gurkan Hizal; Umit Tunca

doi:10.1002/pola.27151

Orthogonal multifunctionalization of aliphatic polycarbonate via sequential Michael addition and radical-thiol-ene click reactions

Bilal Bugra Uysal, Ufuk Saim Gunay, Gurkan Hizal, Umit Tunca^*

^*Corresponding author for this work

Department of Chemistry

Istanbul Technical University

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

27 Citations (Scopus)

Abstract

Aliphatic polycarbonate (PC) copolymer is synthesized by ring opening copolymerization of acrylate- and allyl-functional cyclic carbonate monomers. The post-polymerization functionalization of the resulting copolymer is performed quantitatively using a variety of thiol compounds via sequential Michael addition and photo-induced radical thiol-ene click reactions within relatively short reaction time at ambient temperature. This metal-free click chemistry methodology affords the synthesis of biocompatible PC copolymer with multifunctional groups.

Original language	English
Pages (from-to)	1581-1587
Number of pages	7
Journal	Journal of Polymer Science, Part A: Polymer Chemistry
Volume	52
Issue number	11
DOIs	https://doi.org/10.1002/pola.27151
Publication status	Published - 1 Jun 2014

Keywords

2-mercaptoethanol
Michael addition
NMR
aliphatic polycarbonate (PC)
click reaction
cysteine
gel permeation chromatography (GPC)
multifunctionalization
photo-induced radical thiol-ene
ring opening polymerization (ROP)
thiol-ene

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title = "Orthogonal multifunctionalization of aliphatic polycarbonate via sequential Michael addition and radical-thiol-ene click reactions",

abstract = "Aliphatic polycarbonate (PC) copolymer is synthesized by ring opening copolymerization of acrylate- and allyl-functional cyclic carbonate monomers. The post-polymerization functionalization of the resulting copolymer is performed quantitatively using a variety of thiol compounds via sequential Michael addition and photo-induced radical thiol-ene click reactions within relatively short reaction time at ambient temperature. This metal-free click chemistry methodology affords the synthesis of biocompatible PC copolymer with multifunctional groups.",

keywords = "2-mercaptoethanol, Michael addition, NMR, aliphatic polycarbonate (PC), click reaction, cysteine, gel permeation chromatography (GPC), multifunctionalization, photo-induced radical thiol-ene, ring opening polymerization (ROP), thiol-ene",

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T1 - Orthogonal multifunctionalization of aliphatic polycarbonate via sequential Michael addition and radical-thiol-ene click reactions

AU - Uysal, Bilal Bugra

AU - Gunay, Ufuk Saim

AU - Hizal, Gurkan

AU - Tunca, Umit

PY - 2014/6/1

Y1 - 2014/6/1

N2 - Aliphatic polycarbonate (PC) copolymer is synthesized by ring opening copolymerization of acrylate- and allyl-functional cyclic carbonate monomers. The post-polymerization functionalization of the resulting copolymer is performed quantitatively using a variety of thiol compounds via sequential Michael addition and photo-induced radical thiol-ene click reactions within relatively short reaction time at ambient temperature. This metal-free click chemistry methodology affords the synthesis of biocompatible PC copolymer with multifunctional groups.

AB - Aliphatic polycarbonate (PC) copolymer is synthesized by ring opening copolymerization of acrylate- and allyl-functional cyclic carbonate monomers. The post-polymerization functionalization of the resulting copolymer is performed quantitatively using a variety of thiol compounds via sequential Michael addition and photo-induced radical thiol-ene click reactions within relatively short reaction time at ambient temperature. This metal-free click chemistry methodology affords the synthesis of biocompatible PC copolymer with multifunctional groups.

KW - 2-mercaptoethanol

KW - Michael addition

KW - NMR

KW - aliphatic polycarbonate (PC)

KW - click reaction

KW - cysteine

KW - gel permeation chromatography (GPC)

KW - multifunctionalization

KW - photo-induced radical thiol-ene

KW - ring opening polymerization (ROP)

KW - thiol-ene

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DO - 10.1002/pola.27151

M3 - Article

AN - SCOPUS:84899448550

SN - 0887-624X

VL - 52

SP - 1581

EP - 1587

JO - Journal of Polymer Science, Part A: Polymer Chemistry

JF - Journal of Polymer Science, Part A: Polymer Chemistry

IS - 11

ER -

Orthogonal multifunctionalization of aliphatic polycarbonate via sequential Michael addition and radical-thiol-ene click reactions

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Keywords

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