N‐Chlorosuccinimide (NCS): A Novel Initiator for Atom Transfer Radical Polymerization of Methyl Methacrylate^†

Abstract

Atom transfer radical polymerization (ATRP) of methyl methacrylate (MMA) was achieved, using N-chlorosuccinimide (NCS) as an initiator together with catalytic system CuCl/PMDETA (N,N,N',N',N''-pentamethyldiethylenetriamine), CuCl/MA 5 -DETA (N,N,N',N',N''-penta(methylacrylate)diethylenetriamine), and CuCl/bipy (bipy＝ 2,2'-bipyridyl) respectively. The results indicated that the polymerization possessed typical controlled/living radical polymerization characteristics. The analysis for terminal group of obtained polymer by 1 H NMR proved that NCS is an initiator for ATRP. In comparison with NBS, the polymerization rate was slower and the resulted polymer had narrower molecular weight distribution (MWD) when NCS was employed as the initiator.

Effect of Substituents on the Strength of N–X (X = H, F, and Cl) Bond Dissociation Energies: A High-Level Quantum Chemical Study

“…Nitrogen-centered radicals (derived from N -chloro species) are also of synthetic importance, where they have been used in a number of cyclization processes and homolytic amination reactions of aromatic molecules . From an industrial perspective, N -chloro derivatives of amides, lactams, carbamates, and imides have been shown to be effective initiators for the metal-catalyzed living radical polymerization of methacrylates …”