Issue 39, 2022

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 ⵢⵓⵍ 2022
Accepted
26 ⵖⵓⵛ 2022
First published
02 ⵛⵓⵜ 2022

Polym. Chem., 2022,13, 5530-5535

Expedient synthesis and ring-opening metathesis polymerization of pyridinonorbornenes

S. N. Hancock, N. Yuntawattana, S. M. Valdez and Q. Michaudel, Polym. Chem., 2022, 13, 5530 DOI: 10.1039/D2PY00857B

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