Grafting polysulfonamide from cellulose paper through organocatalytic ring-opening polymerization of N-sulfonyl aziridines

Catalyst-free aziridine-based step-growth polymerization: a facile approach to optically active poly(sulfonamide amine)s and poly(sulfonamide dithiocarbamate)s

“…The electron-withdrawing effect of the sulfonyl group further stabilizes the evolving aza-anion at the growing chain end by delocalization, and propagation continues via sulfonamide anions. Among these two kinds of aziridines, N-sulfonyl aziridines have received considerable attention in recent years, and significant progress has been made by Wurm, Taton, Rupar, et al [17][18][19][20][21][22][23][24][25][26][27][28] Our group employed 2-azaallyl anions, carboxylic acids, cellulose fibers, and hyperbranched polyethyleneimine as the (macro)initiators for the ring-opening polymerization of N-sulfonyl aziridines, respectively, achieving architectural and functionalized poly(N-sulfonyl aziridine) s. [29][30][31][32][33][34][35] However, the polymeric materials based on N-sulfonyl aziridines are still rare, and the chemical structure of the obtained polymers is restricted to polyethyleneimine-derived skeletons.…”

Tributylphosphine-catalyzed aziridine-based cycloaddition polymerization toward thiacyclic polymers

“…[41][42][43][44][45] Modified cellulose paper for oil/water separation and a grafted PEI have been produced. 46,47 Moreover, we recently prepared a new bis(N-sulfonal aziridine) monomer, which can undergo polyaddition reactions with dicarboxylic acids, diphenols, or dithiols toward polysulfonamides in the presence of an organocatalyst. 48 The thioether group has been introduced to the polysulfonamide chain using tributylphosphine as the catalyst (Scheme 1d).…”

Anionic Ring-Opening Polymerizations of N-Sulfonylaziridines in Ionic Liquids

“…Sulfonylaziridines are typically polymerized in polar, aprotic solvents such as DMSO and DMF. The related sulfonylazetidines have also been reported to polymerize in NMP. − Recently, the copolymerization of a sulfonylaziridine with phthalic anhydride to a poly­(ester amide) was reported, and the grafting of polysulfonamides from cellulose, with applications in oil–water separations, was demonstrated …”