Citation: Hui Li, Bai-Ru Ai, Miao Hong. Stereoselective Ring-opening Polymerization of rac-Lactide by Bulky Chiral and Achiral N-heterocyclic Carbenes[J]. Chinese Journal of Polymer Science, ;2018, 36(2): 231-236. doi: 10.1007/s10118-018-2071-5 shu

Stereoselective Ring-opening Polymerization of rac-Lactide by Bulky Chiral and Achiral N-heterocyclic Carbenes

Hui Li ^a,b ,
Bai-Ru Ai ^c ,
Miao Hong ^c,,

a.
Key Laboratory of Marine Materials and Related Technologies, Key Laboratory of Marine Materials and Protective Technologies of Zhejiang Province, Ningbo Institute of Materials Technology and Engineering, Chinese Academy of Sciences, Ningbo 315201, China
b.
University of Chinese Academy of Sciences, Beijing 100049, China
c.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

Corresponding author: Miao Hong, miaohong@sioc.ac.cn
Received Date: 26 September 2017
Accepted Date: 21 October 2017
Available Online: 27 November 2017

Despite the extraordinary success has been achieved in metal catalyst-promoted stereoselective ring-opening polymerization (ROP) of rac-lactide (rac-LA), well-controlled stereoselective rac-LA ROP by organic catalyst still remains a scientific challenge. Here we report our investigations into organocatalytic stereoselective ROP of rac-LA by utilizing novel bulky chiral and achiral N-heterocyclic carbenes (NHC), 1, 3-bis-(1'-naphthylethyl)imidazolin-2-ylidene. The effect of polymerization conditions (e.g. solvent, temperature, alcohol initiator) on ROP behavior by these bulky NHCs has been fully studied, leading to the formation of isotactic-rich stereoblock polylactide (P_i=0.81) under optimized conditions with high activity (Conv.=98% in 30 min) and narrow molecular weight dispersity (Đ=1.05).
- Polylactide,
- Ring-opening polymerization,
- Stereoselectivity,
- Organic catalyst,
- N-heterocyclic carbene
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