While most amide bonds are regarded as robust linkages in chemical environments due to significant resonance stabilization from the nitrogen atom, twisted amides are at odds with this paradigm due to their unique geometric constraints. Removal or weakening of this key stabilizing interaction results in heightened reactivity of the amide carbonyl and nitrogen that provides an opportunity for the development of new directions in polymer science. This presentation will highlight the ways in which a single twisted amide framework has produced a new type of living polymerization, halide-rebound polymerization (HaRP), and also offered a unique driving force in ring-opening metathesis polymerization (ROMP). For each of these topics, effects of geometric distortion on polymerization behavior will be highlighted to provide a rational framework for the development of future twisted amide monomers for precision polymer synthesis.

New opportunities in polymer synthesis using twisted amides

2019 Fall National Meeting

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