Issue 2, 2025

Green synthesis of poly ε-caprolactone using a metal-free catalyst via non-covalent interactions

Abstract

The ring-opening polymerization (ROP) of ε-caprolactone (CL) catalyzed by a metal-free initiator N,N′-dibutyl-N,N,N′,N′-tetramethylethane1,2-diammonium bromide [nBuMe2NCH2CH2NnBuMe2]Br2 (DBTMEDA)Br2 has been investigated. The catalyst (DBTMEDA)Br2 promotes polymerization under mild conditions without any external initiator. Polymerization was demonstrated in a controlled and living manner, producing PCLs with a precisely controlled molecular weight of up to 50 kDa with narrow polydispersity. Density Functional Theory (DFT) calculations indicated the involvement of a C–H⋯O type non-covalent interaction between DBTMEDA cations and the carbonyl group of ε-CL in the monomer activation step. Remarkably, DBTMEDA can also be easily recovered and reused for up to six consecutive cycles without an appreciable decrease in catalytic activity.

Graphical abstract: Green synthesis of poly ε-caprolactone using a metal-free catalyst via non-covalent interactions

Supplementary files

Article information

Article type
Paper
Submitted
03 Sep 2024
Accepted
18 Nov 2024
First published
19 Nov 2024

Green Chem., 2025,27, 527-534

Green synthesis of poly ε-caprolactone using a metal-free catalyst via non-covalent interactions

S. Sagar, P. Nath, S. L. Sunar, A. Ray, M. Choudhary, A. Sarkar, S. K. Singh and T. K. Panda, Green Chem., 2025, 27, 527 DOI: 10.1039/D4GC04411H

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