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Issue 28, 2009
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Generic, SN2 reactive silicone surfaces protected by poly(ethylene glycol) linkers: facile routes to new materials

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Abstract

The efficacy of biomaterials is frequently dependent upon the interface between a synthetic material and the surrounding biology. While silicones offer many benefits in biomaterials applications, they can suffer from insufficient hydrophilicity. We present a controlled and generic route to the surface modification of silicones that permits the introduction of a passivating poly(ethylene glycol) (PEG) layer capped with biologically relevant molecules. High-density, tosylate-modified, PEG-tethered silicone surfaces are readily prepared. These surfaces provide a generic platform for further surface modification by nucleophilic substitution (SN2). The efficiency of substitution at the surfaces was established using a broad variety of nucleophiles: although triphenylphosphine did not modify the tosylated surface, the surface reaction of primary amines, azide, and a thiol was demonstrated to be highly efficient in organic solvents at several temperatures. Changes in surface chemistry and properties were demonstrated by water contact angle, ATR-FTIR, XPS and 13C solid-state NMR spectroscopy.

Graphical abstract: Generic, SN2 reactive silicone surfaces protected by poly(ethylene glycol) linkers: facile routes to new materials

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Article information


Submitted
03 Mar 2009
Accepted
20 Apr 2009
First published
01 Jun 2009

J. Mater. Chem., 2009,19, 5033-5038
Article type
Paper

Generic, SN2 reactive silicone surfaces protected by poly(ethylene glycol) linkers: facile routes to new materials

J. G. Alauzun, J. N. Fortuna, H. Sheardown, F. Gonzaga and M. A. Brook, J. Mater. Chem., 2009, 19, 5033
DOI: 10.1039/B904396A

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