Synthesis and self-assembly of novel fluorous cationic amphiphiles with a 3,4-dihydro-2(1H)-pyridone spacer

The synthesis of fluorous (highly fluorinated) 3,4-dihydro-2(1H)-pyridone-5-carboxylate cationic amphiphiles have been described, where the dihydropyridone serves as a spacer and either a pyridinium bromide or a triphenylphosphonium bromide form the polar cationic head group. The in water self-assembled aggregates have been observed by atomic force microscopy (AFM) and dynamic light scattering (DLS).

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► Four component synthesis of a fluorous 3,4-dihydropyridone-5-carboxylate.
► Allylic bromination of the 6-methyl group using bromine in chloroform and isolation of the 6-bromomethyl-3,4-dihydropyridone product.
► Substitution of the bromine by either pyridine or triphenylphosphine to furnish cationic fluorous 3,4-dihydropyridone-5-carboxylate amphiphiles.
► Self-assembly of the above cationic amphiphiles in aqueous solution forming nanoaggregates which are observed by atomic force microscopy.
► Hydrodynamic diameters of the nanoparticles in solution have been determined by dynamic light scattering.