Ring-Opening Polymerization of Cyclohexene Oxide and Cycloaddition with CO2 Catalyzed by Amine Triphenolate Iron(III) Complexes

Molecules. 2024 May 4;29(9):2139. doi: 10.3390/molecules29092139.

Abstract

A series of novel amine triphenolate iron complexes were synthesized and characterized using UV, IR, elemental analysis, and high-resolution mass spectrometry. These complexes were applied to the ring-opening polymerization (ROP) of cyclohexene oxide (CHO), demonstrating excellent activity (TOF > 11050 h-1) in the absence of a co-catalyst. In addition, complex C1 maintained the dimer in the presence of the reaction substrate CHO, catalyzing the ring-opening polymerization of CHO to PCHO through bimetallic synergy. Furthermore, a two-component system consisting of iron complexes and TBAB displayed the ability to catalyze the reaction of CHO with CO2, resulting in the formation of cis-cyclic carbonate with high selectivity. Complex C4 exhibited the highest catalytic activity, achieving 80% conversion of CHO at a CHO/C4/TBAB molar ratio of 2000/1/8 and a CO2 pressure of 3 MPa for 16 h at 100 °C, while maintaining >99% selectivity of cis-cyclic carbonates, which demonstrated good conversion and selectivity.

Keywords: carbon dioxide; cycloaddition; cyclohexene oxide; iron complexes; ring-opening polymerization.

Grants and funding

This research received no external funding.