Glucose (Glc), galactose (Gal) and fructose based tosylates and triflates were applied as initiators for the living cationic ring opening polymerization (CROP) of 2-ethyl-2-oxazoline (EtOx). In particular, the Glc and Gal triflates induced fast initiation of the CROP as well as a linear increase of the molar mass with conversion. Well-defined Glc as well as Gal a-end functionalized PEtOx was obtained after deprotection. Functionalization of the living oxazolinium chain ends with methacrylate anions resulted in a macromonomer that was applied for the synthesis of a comb polymer being selectively functionalized with Glc at the ends of all side chains via RAFT polymerization. This new general synthetic pathway and the biocompatibility of PEtOx offer the opportunity to benefit from both, the dual responsive properties of the macromolecular bottle brushes as well as the cell targeting capabilities of the carbohydrate functionalities in drug delivery applications.

Sugar based initiators for the cationic ring opening polymerization of 2-ethyl-2-oxazoline

243rd National Meeting (2012)

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