Biomacromolecules, Vol.7, No.2, 411-414, 2006
Synthesis of sugar-substituted poly(phenylenevinylene)s
Sugar-containing PPVs, poly{2-[O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)]-5-methoxy-p-pheny lenevinylenealt-p-phenylenevinylene} (PPV-G1cNAc) and poly{2,5-bis-[O-W-D-glueopyranosyl)]-p-phenylenevinylene-alt-pphenylenev inylene} (PPV-Glc(2)), were synthesized via Heck reaction of p-divinylbenzene (DVB) with O-glycosylated hydroquinones, 2,5-dibromo-4-methoxyphenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranoside (3) and 1,4-bis(O-2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-2,5-dibromobenze ne (6), respectively. Acetyl protecting groups of the PPVs are completely removable under mild conditions (yield 69-87%). The structures were confirmed using H-1 NMR and IR spectra. Size exclusion chromatography (SEC) (eluent: DMF, polystyrene standards) measurements indicated that respective M-n and M-w/M-n values of the obtained polymers are 4.49 x 10(3) and 2.3(5) (PPV-G1cNAc) and 3.86 x 10(3) and 1.3(9) (PPV-Glc(2)). These sugar-containing PPVs are soluble in water/DMF (8/2, v/v) and are recognized by Concanavalin A (Con A), D-glucose-binding protein. Blue shift of gimel(max) of the conjugated polymer backbone was confirmed when the glucose-substituted PPV interacts with Con A. Based on those binding properties, these results revealed that the obtained PPVs with pendant sugars have capabilities for detection of biological stimuli.