Issue 37, 2021

Unprecedentedly high active organocatalysts for the copolymerization of carbonyl sulfide and propylene oxide: steric hindrance effect of tertiary amines

Abstract

The copolymerization of carbonyl sulfide (COS) with epoxides has been developed to be a facile method to synthesize well-defined sulfur-containing polymers. This work describes the steric effect of tertiary amines on the copolymerization of COS with propylene oxide (PO) via a zwitterionic approach, using triethyl borane (TEB) accompanied by various tertiary amines. N,N-Dimethylcyclohexylamine accompanied by TEB (1/1) showed an exceedingly high turnover frequency of up to 69 800 h−1 and a copolymer selectivity of up to >99% for organocatalytic COS/PO copolymerization at 60 °C under solvent-free conditions. The obtained poly(propylene monothiocarbonate)s (PPMTC)s have fully alternating sequences, regioregularity of >99% tail-to-head (T–H) content, and high-number average molecular weights of up to 221.8 kg mol−1 and narrow dispersities (1.1–1.3) within 1 min. We disclosed that tertiary amines (pKa values range from 8.19 to 10.80) with less steric hindrance exhibited higher catalytic activity for COS/PO copolymerization.

Graphical abstract: Unprecedentedly high active organocatalysts for the copolymerization of carbonyl sulfide and propylene oxide: steric hindrance effect of tertiary amines

Supplementary files

Article information

Article type
Paper
Submitted
28 Jul 2021
Accepted
23 Aug 2021
First published
23 Aug 2021

Polym. Chem., 2021,12, 5283-5288

Unprecedentedly high active organocatalysts for the copolymerization of carbonyl sulfide and propylene oxide: steric hindrance effect of tertiary amines

J. Kiriratnikom, X. Yue, J. Yang, Y. Wang, S. Chen, K. Zhang, C. Zhang, M. U. Khan and X. Zhang, Polym. Chem., 2021, 12, 5283 DOI: 10.1039/D1PY01013A

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