Chemical Functionalization of thiol-acrylate polyHIPEs

Abstract

The work described herein describes the synthesis and subsequent functionalization of thiol-acrylate emulsion templated porous polymers (polyHIPEs). Thiol-ene “click” chemistry has been employed in order to produce polyHIPEs from multifunctional thiol and acrylate monomers, and the level of residual thiol within the material determined. These residual thiols have then been used as “reactive handles” which allow for the functionalization of the thiol-acrylate polyHIPE post-polymerization. Both radical mediated thiol-ene “click” and amine catalysed Michael additions have been used in order to graft acrylates to the polymer surface, and the formation of disulphide bonds between the polymer surface and thiols has been explored.
The non-crosslinking monomer pentafluorophenyl acrylate (PFPA) has also been incorporated into thiol-acrylate polyHIPEs in order to provide a route to post-polymerization functionalization. The reaction between the PFPA within the polymer network and amines occurs under mild conditions and so this has been explored as a route to the incorporation of biomolecules in the polymer network.