Bifunctional thiourea-based organocatalyst promoted kinetic resolution polymerization of racemic lactide to isotactic
Jiang Dai1, Wei Xiong1, Dong-Yu Li1
1National Engineering Laboratory of Eco-Friendly Polymeric Materials (Sichuan), College of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China. zzcai@scu.edu.cn.
Abstract:
Here, we prepared a series of thiourea-based organocatalysts 1-7 by combining two stereogenic elements: binaphthyl-amine and cyclohexyl diamine moieties. Catalyst (R,S)-1 facilitated a stereoselective polymerization of rac-LA to afford iso-enriched PDLA with Pm of 0.96 while its enantiomer (S,R)-1 produced PLLA with Pm of 0.96. These iso-enriched PLA contributed to forming a stereocomplexed PLA with a significantly increased Tm of 196 °C.
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