Chemoselective radical polymerization of N-allylmethacrylamide with an aid of complexation with Li+ cation. (26th June 2020)

• Record Type: Journal Article
• Authors: Hirano, Tomohiro; Ogasa, Yuta; Oshimura, Miyuki; Ute, Koichi
• Is Part Of: Polymer. Volume 201(2020)
• Publication Date: 2020-06-26
• Subjects: Radical polymerization -- N-Allylmethacrylamide -- Chemoselective polymerization; Polymers -- Periodicals; Polymerization -- Periodicals; Polymères -- Périodiques; Polymérisation -- Périodiques; 547.7
• DOI: 10.1016/j.polymer.2020.122664
• Languages: English
• ISSNs: 0032-3861

Abstract

Abstract: Radical polymerization of N -allylmethacrylamide (NAlMAAm) was conducted in CH3 CN in the presence or absence of lithium bis(trifluoromethanesulfonyl)imide (LiNTf2 ). The addition of LiNTf2 accelerated the polymerization and affected the molecular weight distribution of the polymers obtained. Polymers with unimodal molecular weight distributions were obtained in the presence of LiNTf2, whereas those with multimodal distributions were obtained in the absence of LiNTf2 . This suggested that LiNTf2 suppressed side reactions such as cross-linking reaction, commonly observed in polymerization of divinyl monomers, and allylic hydrogen abstraction reaction. The 1 H NMR, IR and MALDI-TOF mass analyses of the polymers obtained suggested that the radical polymerization proceeded in a chemoselective manner, leading to preferential formation of linear polymers having pendant allyl groups. Graphical abstract: Image 1 Highlights: Radical polymerization of N -allylmethacrylamide was conducted in CH3 CN in the presence or absence of LiNTf2 . Polymers with unimodal molecular weight distributions were prepared in the presence of LiNTf2 . Chemical structures of polymers were characterized by 1 H NMR & IR spectroscopies and MALDI-TOF mass spectrometry. Linear polymers with pendant allyl groups were successfully prepared in the presence of LiNTf2 . The radical polymerization of the asymmetric divinyl monomer proceeded in a chemoselective manner.