Stereoselective ROP of rac- and meso-Lactides Using Achiral TBD as Catalyst
Sébastien Moins, Sébastien Hoyas, Vincent Lemaur, Beste Orhan, Kayla R. Delle Chiaie, Roberto Lazzaroni, Daniel Taton, Andrew P. Dove, Olivier Coulembier
Abstract
1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD) polymerizes rac-lactide (rac-LA) to form highly isotactic polylactide (PLA) with a Pm = 0.88, while meso-LA yields heterotactic PLA (Pm ~ 0.8) at −75 °C. The stereocontrol of the cryogenic-based ring-opening polymerization comes from a perfect imbrication of both chiral LA and the propagating chiral end-group interacting with the achiral TBD catalyst.
Topics & Concepts
StereoselectivityTacticityCatalysisPolymerizationLactideChemistryPolymer chemistryOrganic chemistryPolymerbiodegradable polymer synthesis and propertiesCarbon dioxide utilization in catalysisOrganometallic Complex Synthesis and Catalysis