Triphenylamine-based fluorescent conjugated glycopolymers: Synthesis, characterization and interactions with lectins

Two well-defined triphenylamine-based fluorescent conjugated glycopolymers were easily synthesized through Suzuki coupling polymerization of peracetylated galactopyranosyl-carrying monomer and consequent efficient deacetylation under Zemplén condition. Their structures were characterized using 1H NMR, IR, and UV–vis spectroscopies. The preliminary insight into carbohydrate–lectin interactions was revealed by the titration of peanut agglutinin (PNA) to one of the final polymers, d-galactose-bearing poly(fluorene-alt-triphenylamine) copolymer (P-2), resulting in a significant fluorescence quenching of the polymer with a Stern–Volmer quenching constant of 1.56 × 105 M−1. Whereas no distinct change in the fluorescent properties of P-2 was observed when concanavalin A (Con A) was employed.