Abstract
We report a new synthetic approach toward cyclic polyureas through alternating copolymerization of aziridines with tosyl isocyanate. Aziridines (ethyleneimine, and (S)-2-benzylaziridine) react with tosyl isocyanate spontaneously in the absence of any catalyst to produce polyureas. The obtained polyureas exhibit an alternating structure as determined by NMR and MALDI-TOF MS analysis. MALDI-TOF analysis indicates that the synthesized polyureas are cyclic. A spontaneous zwitterionic copolymerization mechanism is proposed. DFT calculations reveal that the copolymerization of tosyl isocyanate with ethyleneimine is more kinetically and thermodynamically favored than 2-benzylaziridine.
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