Synthesis of thermoresponsive oxazolone end-functional polymers for reactions with amines using thiol-Michael addition "click" chemistry

The Hien Ho; Martin Levere; Jean Claude Soutif; Véronique Montembault; Sagrario Pascual; Laurent Fontaine

doi:10.1039/c1py00071c

Synthesis of thermoresponsive oxazolone end-functional polymers for reactions with amines using thiol-Michael addition "click" chemistry

The Hien Ho, Martin Levere, Jean Claude Soutif, Véronique Montembault, Sagrario Pascual, Laurent Fontaine

Faculty of Science

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

28 Citations (SciVal)

Abstract

Well-defined poly(N-isopropylacrylamide) (PNIPAM) polymers with an oxazolone ring at the chain end have been synthesized by combining controlled radical polymerization and thiol-Michael addition "click" chemistry. First, PNIPAM was synthesized using reversible addition-fragmentation chain transfer (RAFT) polymerization to afford polymers of controlled molecular weight and molecular weight distribution (M_{n (1H NMR)} = 3200 g mol ^-1; PDI_SEC = 1.05). The chain end was quantitatively converted to a thiol by aminolysis. Then, the functional monomer vinyl azlactone (VDM) was quantitatively "clicked" onto the chain end using a thiol-Michael addition reaction. The polymers were reacted with a model amine in order to demonstrate the potential of these polymers for bioconjugation.

Original language	English
Pages (from-to)	1258-1260
Number of pages	3
Journal	Polymer Chemistry
Volume	2
Issue number	6
DOIs	https://doi.org/10.1039/c1py00071c
Publication status	Published - 1 Jun 2011

ASJC Scopus subject areas

Polymers and Plastics
Organic Chemistry
Biochemistry
Biomedical Engineering
Bioengineering

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10.1039/c1py00071c

Cite this

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abstract = "Well-defined poly(N-isopropylacrylamide) (PNIPAM) polymers with an oxazolone ring at the chain end have been synthesized by combining controlled radical polymerization and thiol-Michael addition {"}click{"} chemistry. First, PNIPAM was synthesized using reversible addition-fragmentation chain transfer (RAFT) polymerization to afford polymers of controlled molecular weight and molecular weight distribution (Mn (1H NMR) = 3200 g mol -1; PDISEC = 1.05). The chain end was quantitatively converted to a thiol by aminolysis. Then, the functional monomer vinyl azlactone (VDM) was quantitatively {"}clicked{"} onto the chain end using a thiol-Michael addition reaction. The polymers were reacted with a model amine in order to demonstrate the potential of these polymers for bioconjugation.",

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T1 - Synthesis of thermoresponsive oxazolone end-functional polymers for reactions with amines using thiol-Michael addition "click" chemistry

AU - Ho, The Hien

AU - Levere, Martin

AU - Soutif, Jean Claude

AU - Montembault, Véronique

AU - Pascual, Sagrario

AU - Fontaine, Laurent

PY - 2011/6/1

Y1 - 2011/6/1

N2 - Well-defined poly(N-isopropylacrylamide) (PNIPAM) polymers with an oxazolone ring at the chain end have been synthesized by combining controlled radical polymerization and thiol-Michael addition "click" chemistry. First, PNIPAM was synthesized using reversible addition-fragmentation chain transfer (RAFT) polymerization to afford polymers of controlled molecular weight and molecular weight distribution (Mn (1H NMR) = 3200 g mol -1; PDISEC = 1.05). The chain end was quantitatively converted to a thiol by aminolysis. Then, the functional monomer vinyl azlactone (VDM) was quantitatively "clicked" onto the chain end using a thiol-Michael addition reaction. The polymers were reacted with a model amine in order to demonstrate the potential of these polymers for bioconjugation.

AB - Well-defined poly(N-isopropylacrylamide) (PNIPAM) polymers with an oxazolone ring at the chain end have been synthesized by combining controlled radical polymerization and thiol-Michael addition "click" chemistry. First, PNIPAM was synthesized using reversible addition-fragmentation chain transfer (RAFT) polymerization to afford polymers of controlled molecular weight and molecular weight distribution (Mn (1H NMR) = 3200 g mol -1; PDISEC = 1.05). The chain end was quantitatively converted to a thiol by aminolysis. Then, the functional monomer vinyl azlactone (VDM) was quantitatively "clicked" onto the chain end using a thiol-Michael addition reaction. The polymers were reacted with a model amine in order to demonstrate the potential of these polymers for bioconjugation.

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Synthesis of thermoresponsive oxazolone end-functional polymers for reactions with amines using thiol-Michael addition "click" chemistry

Abstract

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