Stereoselective ROP of rac- and meso-Lactides Using Achiral TBD as Catalyst

Sébastien Moins (1) , Sébastien Hoyas (1) , Vincent Lemaur (2) , Beste Orhan (3) , Kayla Delle Chiaie (4) , Roberto Lazzaroni (1) , Daniel Taton (3) , Andrew P. Dove (4) , Olivier Coulembier (1)

1 CIRMAP - Centre d'Innovation et de Recherche en Matériaux Polymères
2 UMons - Université de Mons
3 Team 1 LCPO : Polymerization Catalyses & Engineering
4 School of Chemistry [Birmingham]

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.

Mots clés: organocatalyst; stereocontrol; lactide; ring-opening polymerization; TBD

Domaines: Polymères; Catalyse

Sébastien Moins, Sébastien Hoyas, Vincent Lemaur, Beste Orhan, Kayla Delle Chiaie, et al.. Stereoselective ROP of rac- and meso-Lactides Using Achiral TBD as Catalyst. Catalysts, 2020, 10 (6), pp.620. ⟨10.3390/catal10060620⟩. ⟨hal-03278890⟩