Easy access to amphiphilic glycosylated-functionalized polystyrenes

A new route for the synthesis of amphiphilic functionalized polymers based on polystyrene and glycosidic part is described. They were obtained in a three steps procedure combining atom transfer radical polymerization (ATRP), nucleophilic substitution and reductive amination without the need of protection and deprotection steps of the glycosidic part. This process allows the easy synthesis of polystyrenes functionalized by glucose, maltose, maltotriose and dextran. According to the end groups characterization by 1H NMR and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) and the study of the molar masses evolution by size exclusion chromatography, the structures are very well-defined. These amphiphilic polymers were shown to self-associate in aqueous solvent leading to micelles formation as attested by dynamic light scattering measurements.