An aliphatic polycarbonate containing pendant benzyl chloride groups was synthesized by organocatalytic ring opening polymerization (ROP) of a cyclic carbonate monomer (MTC-OCH<sub>2</sub>BnCl). Facile post-polymerization modification of the resultant polymer with various nucleophiles facilitated access to a functionally diverse variety of biodegradable polycarbonate materials in high yield, including those that contained diethanolamine, phosphonium, and azide groups. The azide-functionalized polycarbonates could be further elaborated via Cu-catalyzed click chemistry with alkynyl-functionalized poly(ethylene glycol) (PEG) or pyrene to form the corresponding PEG- or pyrene-grafted polymers. Finally, preliminary results wherein the abovemetioned post-polymerization functionalization of poly(MTC-OCH<sub>2</sub>BnCl) is utilized to modulate the physical properties of self-assembled nanoparticles will be discussed in the context of therapeutic delivery applications.

Benzyl chloride functionalized polycarbonates: A versatile platform for the synthesis of functional biodegradable polycarbonates

249th National Meeting (2015)

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