Tributylphosphine-catalyzed aziridine-based cycloaddition polymerization toward thiacyclic polymers

Abstract

An organocatalytic cycloaddition polymerization approach for the facile synthesis of thiacyclic polymers is established in this work. Bis(N-sulfonyl aziridine)s and diisocyanates are employed as the monomers, and they undergo cycloaddition...

Diversity-oriented synthesis of chemically recyclable poly(sulfonamide ester)s through organocatalytic aziridine-based multicomponent polymerization

“…Step-growth polymerization of bis(N-sulfonyl aziridine)s (our previous work 35,36,38 and this work).…”

“…37 Besides polyaddition, cycloaddition polymerization of bis( N -sulfonyl aziridine) with diisocyanates can produce novel poly(thiazolidin-2-imine)s (Scheme 1). 38 These achievements revealed the big potential of the aziridine building block toward diverse structural polymers.…”

Rapid synthesis of functional poly(ester amide)s through thiol–ene chemistry

“…For example, Yoon and Zhang independently reported a series of bis(N-sulfonyl aziridine) monomers, which can be polymerized with various dinucleophiles such as dicarboxylic acids, diphenols, dithiols and diamines. [25][26][27][28][29] We recently reported on chain-growth AROP of carbamate activated aziridines 11 and the step-growth polymerization bis(Ncarbonyl aziridine)s with dinucleophiles (Scheme 1d). 30 We found that bis(N-carbonyl aziridine)s rapidly polymerize with a variety of dinucleophiles, including dicarboxylic acids to produced PEAs.…”

“…For example, Yoon and Zhang independently reported a series of bis( N -sulfonyl aziridine) monomers, which can be polymerized with various dinucleophiles such as dicarboxylic acids, diphenols, dithiols and diamines. 25–29…”

Carbonyl Aziridines: Strained Amides for Rapid Polyamide Synthesis

“…Our work builds on the development of the anionic polymerization of N -sulfonyl aziridines (Scheme b), which are now recognized as valuable monomers to prepare poly­( N -sulfonyl aziridine), poly­(sulfonamide amine), polyimines, thiacyclic polymers, and poly­( N -sulfonyl aziridine) containing copolymers and composites. − We have also recently reported the polymerization of a tert -butyloxycarbonyl (BOC)-activated aziridine, demonstrating that non-sulfonyl electron-withdrawing groups can support anionic aziridine polymerizations . The versatility of N -sulfonyl aziridines has expanded with reports that bis­( N -sulfonyl aziridine)­s form polysulfonamides, the sulfonyl analogues of amides, upon reaction with dinucleophiles.…”