It is known that the synthesis of fluorinated 2-oxazoline-based homo- and copolymers suffers from extremely low activity of 2-perfluoroalkyl-2-oxazolines in cationic ring-opening polymerization reaction (CROP), both in the initiation as in the propagation. The introduction of strong electron-withdrawing perfluoroalkyl substituents in the 2-substituent of the 2-oxazoline ring significantly decreases the reactivity of the monomer and respective propagating chain ends as this diminishes the nucleophilicity of the imine drastically. We were able to overcome the bottleneck of the synthesis by the insertion of hydrocarbon spacer between 2-oxazoline ring and trifluoromethyl group. New fluorine-containing 2-alkyl-2-oxazolines were synthesized (Figure 1) and their ability to polymerize by CROP was studied. The kinetic measurements show the gradual increase of the rate of polymerization with the increase of the length of hydrocarbon spacer under standard polymerization conditions. A number of fluorine-containing di- and triblock copolymers with 2-methyl-2-oxazoline (hydrophilic) and 2-octyl-2-oxazoline (hydrophobic) were synthesized. All synthesized polymers were studied by a series of physico-chemical methods such as dynamic light scattering (DLS), small angle X-ray scattering (SAXS), cryo-TEM microscopy, etc. It has been proven that the micellar-like structures are present in diluted aqueous solutions.

Novel fluorinated 2-alkyl-2-oxazolines: Three-fold increasing of reactivity in polymerization reaction

254th National Meeting (2017)

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