Dual stimuli-responsive polyamines derived from modified N-vinylpyrrolidones through CuAAC click chemistry

The synthesis via copper(I)-catalyzed azide alkyne cycloaddition (CuAAC) of three new monomer derivatives of N-vinyl-2-pyrrolidone (VP) carrying cyclic pyrrolidine, piperidine, and piperazine groups and the corresponding copolymers with unmodified VP is shown. The systems bearing pyrrolidine and piperidine displayed both thermo- and pH-response, which has not been reported previously for a polymer with polyvinylpyrrolidone (PVP) backbone. A broad modulation of the LCST with the copolymer composition and pH was observed in a temperature range 0-100 °C. The polymers carrying piperazine exhibited broad buffering regions and no thermosensitivity.The authors gratefully acknowledge support from the grants ref. MAT-2010-20001 and MAT2013-42957-R. A. del Prado acknowledges the Ministry of Economy and Competitiveness, Spain, for the FPI grant. R. Navarro gratefully acknowledges funding from the Spanish Research Council (CSIC) and European Social Fund (ESF) through the JAE-doc program.Peer Reviewe