Issue 4, 2009
From the journal:

Soft Matter

Click chemistry as a means to functionalize macroporous PolyHIPE

David Cummins,a   Christopher J. Duxbury,b   Peter J. L. M. Quaedflieg,b   Pieter C. M. M. Magusin,a   Cor E. Koninga  and  Andreas Heise*ab  

* Corresponding authors

a Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven, The Netherlands
E-mail: a.heise@tue.nl
Fax: + 31 (0)46 4763949
Tel: + 31 (0)46 4761119

b DSM Research, P.O. Box 18, 6160 MD Geleen, The Netherlands

Abstract

The surface functionalization of macroporous polyHIPE (pHIPE) was achieved by Huisgen-type ‘click’ chemistry. In the first step a 600–800 nm thick layer of poly(glycidyl methacrylate) (pGMA) was grafted from the pHIPE surface by atom transfer radical polymerization (ATRP). Near quantitative azidation of the pGMA layer was achieved by the ring-opening reaction of the epoxide groups with sodium azide. The influence of the reaction conditions on the uniformity of the ‘click’ reaction on the three-dimensional macroporous materials was shown in model reactions with propargyl alcohol. Under optimized conditions, azide conversions of around 80% were estimated from IR-spectra. Visualization of the homogeneous functionalization was achieved by the attachment of a fluorescent molecule. Moreover, the first proof of the versatility for biofunctionalization of pHIPE by this method was provided by the attachment of several protected amino acids. The hydrolytic stability of the triazole ring allows for the successful deprotection of the amino acids on the pHIPE.

Graphical abstract: Click chemistry as a means to functionalize macroporous PolyHIPE

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Article information

DOI
https://doi.org/10.1039/B810823D
Article type
Paper
Submitted
25 Jun 2008
Accepted
27 Oct 2008
First published
08 Dec 2008

Soft Matter, 2009,5, 804-811

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Click chemistry as a means to functionalize macroporous PolyHIPE

D. Cummins, C. J. Duxbury, P. J. L. M. Quaedflieg, P. C. M. M. Magusin, C. E. Koning and A. Heise, Soft Matter, 2009, 5, 804 DOI: 10.1039/B810823D

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