Issue 37, 2021

Organocatalytic sequential ring-opening polymerization of cyclic ester/epoxide and N-sulfonyl aziridine: metal-free and easy access to block copolymers

Abstract

We report an organocatalytic sequential ring-opening polymerization (ROP) approach for the facile synthesis of polysulfonamide-based copolymers. Alcohols and methoxylpolyethylene glycols were initially employed as (macro)initiators for the ROP of N-sulfonyl aziridines to produce well-controlled polymers with the assistance of tosyl isocyanate. Tosyl isocyanate efficiently transformed the hydroxyl species into the tosylcarbamate anion, the initiating site for the ROP of N-sulfonyl aziridines. ROP of ε-caprolactone or propylene oxide was then performed in bulk in the presence of the phosphazene base t-Bu-P2 or t-Bu-P4, followed by end-group transformation with tosyl isocyanate and the subsequent ROP of N-sulfonyl aziridines. The synthesized poly(ε-caprolactone)-block-polysulfonamide and poly(propylene oxide)-block-polysulfonamide copolymers showed a remarkable control of molar masses and dispersities. Well-defined triblock and 3-arm star-shaped copolymers were successfully prepared from diol and triol initiators.

Graphical abstract: Organocatalytic sequential ring-opening polymerization of cyclic ester/epoxide and N-sulfonyl aziridine: metal-free and easy access to block copolymers

Supplementary files

Article information

Article type
Paper
Submitted
02 Jul 2021
Accepted
26 Aug 2021
First published
26 Aug 2021

Polym. Chem., 2021,12, 5328-5335

Organocatalytic sequential ring-opening polymerization of cyclic ester/epoxide and N-sulfonyl aziridine: metal-free and easy access to block copolymers

H. Huang, W. Luo, L. Zhu, Y. Wang and Z. Zhang, Polym. Chem., 2021, 12, 5328 DOI: 10.1039/D1PY00890K

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