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One-pot tandem ring-opening polymerization of N-sulfonyl aziridines and “click” chemistry to produce well-defined star-shaped polyaziridines
Authors:Wenyi Luo  Ying Wang  Yaocheng Jin  Zhen Zhang  Chuande Wu
Institution:School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou, China
Abstract:An effective approach for fast synthesis of well-defined star-shaped poly(2-methyl-N-tosylaziridine)s was developed by one-pot tandem ring-opening polymerization (ROP) of N-sulfonyl aziridines with trimethylsilyl azide (TMSN3) and “click” reaction with alkynes. Azido terminated polyaziridines (α-N3-PAzs) could be achieved via ROP of N-sulfonyl aziridines with TMSN3 in the presence of organic superbases. The catalytic efficiency of organobases, including 1,4-diazabicyclo2.2.2]octane (DABCO), 1,8-diazabicyclo5.4.0]-7-undecene (DBU), 7-methyl-1,5,7-triazabicyclo4.4.0]dec-5-ene (MTBD), 1,5,7-triazabicyclo4.4.0]dec-5-ene (TBD), and N,N,N′,N″,N″-pentamethyldiethylenetriamine (PMDETA), was evaluated, and all of them except TBD afforded “living”/controlled ROP of 2-methyl-N-tosylaziridines (TsMAz). Star-shaped polyaziridines were then fastly synthesized by the one-pot tandem strategy. During the reaction process, PMDETA catalyzed ROP first, then was triggered to be a ligand by adding CuBr for “click” reaction. Well-defined 3- and 4-arm star P(TsMAz)s were successfully prepared, and subsequently desulfonylated to give star-shaped polypropylenimines (PPIs). PPI stars exhibited intrinsic photoluminescence properties from the polyamine arms.
Keywords:“click” chemistry  organocatalyst  ring-opening polymerization  star polymer  tandem polymerization
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