Prepolymerization and Postpolymerization Functionalization Approaches to Fluorescent Conjugated Carbazole-Based Glycopolymers via "Click Chemistry"

Facile prepolymerization and postpolymerization functionalization approaches to prepare well-defined fluorescent conjugated glycopolymers through Cu(I)-catalyzed azide/alkyne "Click" ligation were explored. Two well-defined carbazole-based fluorescent conjugated glycopolymers were readily synthesized based on these strategies and characterized by H-1 NMR, C-13 NMR, IR spectra, and UV-vis spectra. The "Click" ligation offers a very effective conjugation method to covalently attach carbohydrate residues to fluorescent conjugated polymers. In addition, the studies of carbohydrate-lectin interactions were performed by titration of concanavalin A (Con A) to D-glucose-bearing poly(anthracene-alt-carbazole) copolymer P-2 resulting in significant fluorescence quenching of the polymer due to carbohydrate-lectin interactions. When peanut agglutinin (PNA) was added, no distinct change in the fluorescent properties of P-2 was observed. (c) 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 2948-2957, 2009