Expedient synthesis and ring-opening metathesis polymerization of pyridinonorbornenes

Abstract

Pyridine-containing polymers are promising materials for a variety of applications from the capture of contaminants to the self-assembly of block copolymers. However, the innate Lewis basicity of the pyridine motif often hampers living polymerization catalyzed by transition-metal complexes. Herein, we report the expedient synthesis of pyridinonorbornene monomers via a [4 + 2] cycloaddition between 2,3-pyridynes and cyclopentadiene. Well-controlled ring-opening metathesis polymerization was enabled by careful structural design of the monomer. Polypyridinonorbornenes exhibited high Tg and Td, a promising feature for high-temperature applications. Investigation of the polymerization kinetics and of the reactivity of the chain ends shed light on the influence of nitrogen coordination on the chain-growth mechanism.

Graphical abstract: Expedient synthesis and ring-opening metathesis polymerization of pyridinonorbornenes

Supplementary files

Article information

Article type
Communication
Submitted
02 Jul 2022
Accepted
26 Aug 2022
First published
02 Sep 2022

Polym. Chem., 2022, Advance Article

Expedient synthesis and ring-opening metathesis polymerization of pyridinonorbornenes

S. N. Hancock, N. Yuntawattana, S. M. Valdez and Q. Michaudel, Polym. Chem., 2022, Advance Article , DOI: 10.1039/D2PY00857B

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