Arduengo's landmark isolation of the first stable N-heterocyclic carbenes (NHCs) in 1991 spurred widespread application of NHCs in catalysis, organic electronics, and biomaterials.  Despite these advances, relatively little work has been directed towards the use of NHC-based systems for metal ion detection and nanoparticle stabilization: areas of tremendous biological and medicinal significance.  We sought to develop a high-throughput synthetic approach that would enable the preparation of libraries of NHC-based polymeric ligands for these applications.  To that end, we undertook the synthesis of terminal alkyne-functionalized imidazolium salts, which represent modular NHC precursor building blocks.  Copolymerization of these monomers with a series of a,?-bis-azidooligo(ethylene glycol)s via the copper(I)-catalyzed azide-alkyne cycloaddition led to a library of water-soluble, poly(ethylene glycol)-alt-imidazolium copolymers.  The resulting �click-o-mers� contain embedded NHC functional groups and triazole rings; these materials were tested for their ability to stabilize gold nanoparticles and bind metal cations in a selective fashion.

Click-o-mers with N-heterocyclic carbenes for sensing metal ions and stabilizing gold nanoparticles

244th National Meeting (2012)

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