Synthesis and Chiral Micellization Behavior of Optically Active Amphiphilic Diblock Copolymer Bearing Quinine Pendants

A novel optically active amphiphilic diblock copolymer bearing quinine pendants poly(ethylene oxide)-b-poly(glycidyl triazolyl-L-quinine) (MPEO-b-PGTQ) was synthesized by "click" reaction of alkyne-modified diblock copolymer poly(ethylene oxide)-b-poly(glycidyl propargyl ether) (MPEO-b-PGPE) and 9-N(3)-quinine. The structure and composition of copolymers were characterized by gel permeation chromatography, (1)H nuclear magnetic resonance spectroscopy ((1)H NMR), elemental analysis and optical rotation measurements, which showed that the synthetic route could provide the copolymer with well-defined composition and with similar optical activity compared to its parent quinine. The micellization behavior of this chiral copolymer was investigated in different solvent systems. The results from fluorescence spectroscopy, UV spectroscopy, dynamic light scattering, transmission electron microscopy, (1)H NMR and circular dichroism (CD) spectroscopy indicated that the MPEO-b-PGTQ could form regular chiral spherical micelles in H(2)O and Tetrahydrofuran-H(2)O (10:90, V/V) systems, and the state of aggregated chiral micelles depended on the nature of the medium. (C) 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 3640-3650, 2009