Issue 41, 2023

Ring-opening polymerization of functionalized aliphatic bicyclic carbonates

Abstract

A series of six-membered bicyclic carbonates has been prepared from an alcohol precursor through esterification, etherification and silyl-etherification methods to afford functional monomers with synthetically useful vinyl, allyl, alkynyl and polymerizable groups that allow for orthogonal polymerization strategies. Anionic ring-opening polymerization (AROP) of these monomers allows us to access densely functional aliphatic polycarbonates with Mn's and Tg's in the range of 3.2–11.7 kg mol−1 and 11–106 °C, respectively. Bifunctional monomers comprising two separate polymerizable groups can be selectively polymerized via AROP or radical based/ring-opening metathesis polymerization methods. Selected polycarbonates were post-modified via thiol–ene chemistry to further modulate their properties. Finally, base-mediated depolymerization of these new polycarbonates was attempted giving rise to an unusual bicyclic oxetane product, which may be upcycled through appropriate copolymerization methods.

Graphical abstract: Ring-opening polymerization of functionalized aliphatic bicyclic carbonates

Supplementary files

Article information

Article type
Paper
Submitted
24 Jul 2023
Accepted
28 Aug 2023
First published
06 Oct 2023
This article is Open Access
Creative Commons BY-NC license

Polym. Chem., 2023,14, 4748-4753

Ring-opening polymerization of functionalized aliphatic bicyclic carbonates

J. Ni, M. Lanzi, D. H. Lamparelli and A. W. Kleij, Polym. Chem., 2023, 14, 4748 DOI: 10.1039/D3PY00860F

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