Catenane Formation of a Cyclic Poly(alkyl Sorbate) Chain-growth Polymerization Induced by an N-heterocyclic Carbene and Ring-closing Without Extreme Dilution

Overview

Journal RSC Adv

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2023 May 8

PMID 37152560

Authors

Hirotake Yato

Kota Oto

Akinori Takasu

Masahiro Higuchi

Affiliations

Soon will be listed here.

Abstract

1,3-Di--butylimidazol-2-ylidene (NHCBu), a typical N-heterocyclic carbene (NHC), was previously found to induce the anionic chain-growth polymerization of ethyl sorbate (ES) in the presence of an aluminum Lewis acid, , methylaluminum bis(2,6-di--butyl-4-methylphenoxide) (MAD), in which the neighboring of α-terminal dienolate with a propagating anion induced cyclization without highly diluted conditions, after monomer depletion, to give the cyclic poly(ES). In this paper, we report that catenane formation occurs by two-step polymerization of ethyl sorbate (ES), in which, after complete monomer (ES) consumption ([ES]/[NHCBu] = 100/1) in toluene followed by purification by reprecipitation, a second addition of ES monomer ([ES]/[ NHCBu] = 20/1) in another pot (in toluene or tetrahydrofuran (THF)) resulted in catenane formation, namely a polycatenane. TEM images of a sample from the second step polymerization in THF revealed particles of polycatenane structure consisting of cyclic poly(ES) with sizes ranging from 200 to 1000 nm, showing that this NHCBu triggered chain polymerization and successive cyclization without highly diluted conditions enabled us to fabricate the intended polycatenane in the successive two-step polymerization.

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