Polym. Chem. [SRCO]

Abstract :

he present report describes the first use of unprotected and “free” N-heterocyclic carbenes (NHCs), such as IMes, IPr and air-stable Cl-IPr carbenes, as single component initiators for the alternating ring-opening co-polymerization (ROCOP) of cyclic anhydrides (phthalic anhydride, PA; succinic anhydride, SA) and various epoxides to efficiently and selectively access the corresponding polyesters in a well-defined manner and as metal-free materials. In the case of ROCOP runs with PA as the anhydride source, control experiments are in line with an initiation via ring-opening of PA by the NHC moiety, as established with the synthesis and structural characterization of the IMes-PA ring-opened product 1. The present NHC systems were further exploited as ROCOP initiators of PA and bio-sourced epoxides such as eugenyl glycidyl ether (EGE) and safrole glycidylether (SO) yielding the production of regioregular p(PA-alt-EGE) polyester, as well as p(PA-alt-SO), a novel polyester material.

Graphical Abstract:

 

Reference :

Printz, G.; Shuvo, R. G.; Schweizer, A.; Ryzhakov, D.; Gourlaouen, C.; Lantigner, L.; Jacques, B.; Messaoudi, S.; Le Bideau, F.; Dagorne, S.

N-Heterocyclic Carbene-Initiated Epoxide/Anhydride Ring-Opening Copolymerization: Effective and Selective Organoinitiators for the Production of Various Polyesters

Polym. Chem. 2024. DOI:  https://doi.org/10.1039/D4PY00778F.

Contact :

Samuel Dagorne, équipe SRCO, Institut de Chimie de Strasbourg (UMR 7177).