It is well known that stereochemistry in the polymer backbone can greatly impact bulk material properties with natural rubber (cis-polyisoprene) being much more elastic than the comparatively brittle gutta-perch (trans-polyisoprene). While, the stereospecific metal-catalyzed polymerization of dienes (e.g., isoprene or butadiene) has been well studied, broader application of this concept in new functional thermoplastic elastomers is relatively unexplored. To synthesize new polymers containing π-bonds in the backbone, the efficient nucleophilic thiol-yne addition reaction was exploited. By varying amine bases for the thiol activation, the π-bond stereochemistry of the α,β-unsaturated carbonyl moiety can be tuned from approximately 30 – 80 % cis content. It was found that thermomechanical properties of the resultant polymers are greatly dependent on overall cis content and can be tuned accordingly. Results suggest that these polymers are also biocompatible and stable to hydrolytic degradation in basic media thus making them suitable for long term use in biomedical devices.

Adjusting properties of biocompatible thermoplastics via π-bond stereochemistry

256th National Meeting (2018)

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