Issue 31, 2021

A chiral thiourea and a phosphazene for fast and stereoselective organocatalytic ring-opening-polymerization of racemic lactide

Abstract

Control of stereoregularity is inherent to precision polymerization chemistry for the development of functional materials. A prototypal example of this strategy is the ring-opening polymerization (ROP) of racemic lactide (rac-LA), a bio-sourced monomer. Despite significant advances in organocatalysis, stereoselective ROP of rac-LA employing chiral organocatalysts remains unexplored. Here we tackle that challenge by resorting to Takemoto's catalyst, a chiral aminothiourea, in the presence of a phosphazene base. This chiral binary organocatalytic system allows for fast, chemo- and stereoselective ROP of rac-LA at room temperature, yielding highly isotactic, semi-crystalline and metal-free polylactide, with a melting temperature as high as 187 °C.

Graphical abstract: A chiral thiourea and a phosphazene for fast and stereoselective organocatalytic ring-opening-polymerization of racemic lactide

Supplementary files

Article information

Article type
Communication
Submitted
10 Dec 2020
Accepted
11 Mar 2021
First published
11 Mar 2021

Chem. Commun., 2021,57, 3777-3780

A chiral thiourea and a phosphazene for fast and stereoselective organocatalytic ring-opening-polymerization of racemic lactide

M. S. Zaky, A. Wirotius, O. Coulembier, G. Guichard and D. Taton, Chem. Commun., 2021, 57, 3777 DOI: 10.1039/D0CC08022E

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