Hydrazine-Catalyzed Ring-Opening Metathesis Polymerization of Cyclobutenes

24 May 2024, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Materials formed by the ring-opening metathesis polymerization (ROMP) of cyclic olefins are highly valued for industrial and academic applications but are difficult to prepare free of metal contaminants. Here we describe a highly efficient metal-free ROMP of cyclobutenes using hydrazine catalysis. Reactions can be initiated via in situ condensation of a [2.2.2]-bicyclic hydrazine catalyst with an aliphatic or aromatic aldehyde initiator. The polymerizations show living characteristics, achieving excellent control over molecular weight, low dispersity values, and high chain-end fidelity. Additionally, the hydrazine can be used in substoichiometric amounts relative to the aldehyde chain-end while maintaining good control over molecular weight and low dispersity values, indicating that a highly efficient chain transfer mechanism is occurring.

Keywords

ROMP
Hydrazine-catalyzed

Supplementary materials

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Description
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Supporting Information
Description
Experimental procedures and product characterization data including 1H and 13C NMR spectra, and HRMS for all new compounds; GPC, TGA, and DSC data for selected polymers.
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