Poly(N-substituted glycine)s, also referred to as polypeptoids, are interesting polymers for life science and materials science applications. They are available by controlled ring-opening polymerization of N-substituted glycine N-carboxyanhydrides (NCAs) and their properties, for instance solution properties including thermo-responsivity, can be tailored by the nature of the side chain. Polypeptoids with unsaturated side chains can be further functionalized by click chemistry including thiol-ene/yne photochemistry.Poly(N-C3 glycine)s (C3 = n-propyl, allyl, and isopropyl) with molecular weights ranging from 1.8-6.6 kDa readily soluble in water (up to 20-40 g/L) and show LCST behavior; the cloud point temperatures vary between 15 and 58 �C depending on C3 and molecular weight. Poly(N-propargyl glycine), on the other hand, does not dissolve in water. Long-term annealing of aqueous solutions of poly(N-(n-propyl) glycine) and poly(N-allyl glycine) above their phase transition temperature results in the formation of crystalline microparticles with rose bud type morphology.Poly(N-(n-propyl) glycine)-block-poly(N-methyl glycine) form core-shell micelles in water at above the phase transition temperature of the first block, i.e. >30 �C. Crystallization of the poly(N-(n-propyl) glycine) core produces sub-micron particles, which are larger in size and have different morphology than the original micelles. Kinetics/mechanism of the aggregation and crystallization processes are currently being examined.

Thermoresponsive polypeptoids

248th National Meeting (2014)

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