Copper(I) bromide coordinated by the ionic liquid 1‐[(diethyl amine)amine]ethyl‐3‐methyl imidazolium chloride to catalyze the atom transfer radical polymerization of methyl methacrylate in 1‐allyl‐3‐methyl imidazolium chloride

Abstract

ABSTRACTA coordinating ionic liquid (IL), 1‐[(diethyl amine)amine]ethyl‐3‐methyl imidazolium chloride ([N3MIM]Cl), was prepared as an alternative to a simple organic ligand to coordinate to copper(I) bromide (CuBr). We, thereby, obtained a novel catalyst for atom transfer radical polymerization (ATRP) reactions. This catalyst was applied to the ATRP of methyl methacrylate in the IL 1‐allyl‐3‐methyl imidazolium chloride ([AMIM]Cl). The chemical structures of the ILs obtained were confirmed by Fourier transform infrared spectroscopy, mass spectrometry, and 1H‐NMR analyses. The coordination ability of [N3MIM]Cl was assessed by cyclic voltammetry, and the redox potential of [N3MIM]Cl–CuBr was −0.507 V. The [N3MIM]Cl–CuBr complex was expected to be a markedly more active catalyst than the amine DETA–CuBr complex. The coordination mode toward CuBr was also examined. The [N3MIM]Cl–CuBr catalyst system showed good controllability in the aforementioned ATRP reaction in [AMIM]Cl. The Cu catalyst was easily separated from the obtained polymer with the coordinating IL as a ligand. Consequently, the coordinating IL overcame the shortcomings of traditional organic ligands, such as poor compatibility with IL media and poor separation of the catalyst from the polymer; this makes it highly promising for applications in the ATRP field. © 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2017, 134, 45484.