This presentation will describe the synthesis of chiral and sustainable polymers. Enantiomeric zirconocenium ester enolate catalysts have been synthesized and utilized in the asymmetric coordination polymerization of prochiral functionalized vinyl monomers towards optically-active, one-handed helical polymers. These enantiomeric catalysts have also been used in the successful kinetic resolution polymerization of a racemic methacrylamide monomer. The stereospecific polymerization of chiral oxazolidinone functionalized alkenes has been performed, producing highly isotactic polymers that assume helical or random-coil secondary conformations, dictated by the proximity of the chiral oxazolidinone to the main-chain of the polymer.  Investigating applications of helical polymers, two pseudo-enantiomeric helical poly(phenyl acetylene)s bearing chiral organocatalyst side-groups have been synthesized and the effects of the helicity on the enantioselectivity of these catalysts was examined. Lastly, the ability of cinchona alkaloid organocatalysts to catalyze the ring opening polymerization of lactide was studied, revealing the first organocatalyst mediated kinetic resolution polymerization of this racemic monomer.

Polymerization catalysis for precision synthesis of chiral and sustainable polymers

244th National Meeting (2012)

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