Isoselective Lactide Ring Opening Polymerisation using [2]Rotaxane Catalysts

Jason Y C Lim; Nattawut Yuntawattana; Paul D Beer; Charlotte K Williams

doi:10.1002/anie.201901592

Isoselective Lactide Ring Opening Polymerisation using [2]Rotaxane Catalysts

Angew Chem Int Ed Engl. 2019 Apr 23;58(18):6007-6011. doi: 10.1002/anie.201901592. Epub 2019 Mar 28.

Authors

Jason Y C Lim^{1

2}, Nattawut Yuntawattana¹, Paul D Beer¹, Charlotte K Williams¹

Affiliations

¹ Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK.
² Current address: Institute of Materials Research and Engineering, 2 Fusionopolis Way, Singapore, 138634, Singapore.

Abstract

Polylactide (PLA) is a fully biodegradable and recyclable plastic, produced from a bio-derived monomer: it is a circular economy plastic. Its properties depend upon its stereochemistry and isotactic PLA shows superior thermal-mechanical performances. Here, a new means to control tacticity by exploiting rotaxane conformational dynamism is described. Dynamic achiral [2]rotaxanes can show high isoselectivity (P_i =0.8, 298 K) without requiring any chiral additives and enchain by a chain end control mechanism. The organocatalytic dynamic stereoselectivity is likely applicable to other small-molecule and polymerization catalyses.

Keywords: isoselectivity; lactide; organocatalysis; ring-opening polymerisation; rotaxane.

Publication types

Research Support, Non-U.S. Gov't

Abstract

Publication types

Grants and funding