N-Heterocyclic carbenes (NHCs) have received increasing attention over the last past 20 years because of their particular steric and electronic properties. They have recently emerged as organocatalysts in the context of polymer chemistry, allowing the precise synthesis of a wide range of macromolecules by chain- or step-growth polymerization processes1-3. Generally, aziridines polymerize via a cationic pathway, affording non-controlled hyper-branched poly(ethylene imine). Interestingly, it was recently shown that aziridines could be activated toward anionic ring-opening polymerization (AROP) by N-tosylation4,5. In this work, the ring-opening polymerization of activated aziridines catalyzed by a NHC, namely 1,3-bis(isopropyl)-4,5(dimethyl)imidazol-2-ylidene, have been investigated in presence of various initiators6,7. In the proposed approach, different activated N-sulfonyl amines, non-activated secundary amine, trimethylsilyl azide as well as amino-alcohols can be used as an initiator and molar masses are controlled by adjusting the initial monomer/initiator feed ratio. Characterizations by SEC, NMR and MALDI-ToF MS are consistent with a living/controlled organocatalytic ROP of N-tosyl aziridines.

n-Heterocyclic carbene organocatalyzed ring-opening polymerization of n-tosyl aziridines using functional initiators and amino-alcohols as bifunctional and double headed initiators

255th National Meeting (2018)

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