Issue 6, 2011
From the journal:

Polymer Chemistry

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

The Hien Ho,a   Martin Levere,a   Jean-Claude Soutif,a   Véronique Montembault,a   Sagrario Pascuala  and  Laurent Fontaine*a  

* Corresponding authors

a UCO2M, UMR CNRS 6011, Université du Maine, Avenue Olivier Messiaen, Le Mans, France
E-mail: laurent.fontaine@univ-lemans.fr
Fax: +33 (0)2 4383 3754
Tel: +33 (0)2 4383 3325

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.

Graphical abstract: Synthesis of thermoresponsive oxazolone end-functional polymers for reactions with amines using thiol-Michael addition “click” chemistry

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C1PY00071C
Article type
Communication
Submitted
08 Feb 2011
Accepted
19 Mar 2011
First published
16 May 2011

Polym. Chem., 2011,2, 1258-1260

Permissions

Request permissions

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

T. H. Ho, M. Levere, J. Soutif, V. Montembault, S. Pascual and L. Fontaine, Polym. Chem., 2011, 2, 1258 DOI: 10.1039/C1PY00071C

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements