THIOL-YNE CHEMISTRY AS A NOVEL APPROACH TO THE SYNTHESIS OF MOLECULARLY IMPRINTED POLYMERS
2Christian Doppler Laboratory for Functional and Polymer Based Ink-Jet Inks, University of Leoben
Thiol-yne chemistry as a means for polymerization offers several advantages over the more common free-radical technique (FRP). These include step-growth mechanism,1 oxygen tolerance,2,3 compatibility with (meth)acrylic monomers4,5 and generally, much easier degradable matrices.6 Despite these advantages, there has only been one and recent application of thiol-yne chemistry to the synthesis of molecularly imprinted polymers (MIPs).7 In this study, we demonstrate using propranolol as model template8 that thiol-yne chemistry represents a very convenient alternative to FRP for the synthesis of MIPs.9 A formulation containing a dialkyne, a polythiol10 and acrylic acid as the functional monomer has been UV-polymerized at 365 nm in the presence of propranolol, without the need of previous degassing with nitrogen or argon to remove the oxygen. In just a few minutes, a highly specific MIP was obtained with the reference NIP showing virtually no binding. Despite a short polymerization time, high conversion of the carbon triple bond was obtained. Moreover, thiol-yne matrices have shown to be more easily degradable by hydrolysis, in contrast to conventional MIPs synthesized by FRP, thus limiting their potential impact into the environment. Our results show a novel and promising application of the thiol-yne chemistry for MIP fabrication.
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