A comparative study of micellization with fluorinated and hydrogenated diquaternary ammonium bolaamphiphiles

• Fluorinated and hydrogenated cationic bolaamphiphiles have been synthesized.
• Structural conformations at the air–water or in solution are reported.
• The effect of added salt or lipid DOPE results in aggregates of various kinds and sizes.
• DOPE-fluorinated and DOPE-hydrogenated surfactant complexes show differences.

Two new Na,Nb-Bis[3-(trimethylamino)propyl]-perfluoroalkanes diamide-Iodide with (a = 1; b = 10) and (a = 1; b = 12), differing by the fluorocarbon tail spacer (8 or 10 CF2), and the N1,N12-Bis[3-(trimethylamino)propyl]-dodecanediamide-Iodide have been synthesized in two steps involving the appropriate dimethyl perfluoro or hydrogeno alkane dicarboxylate, N,N-dimethyl-1,3-propane diamine, and methyl iodide. Their surface properties were studied at 45 °C in aqueous solutions using conductivity, surface tension, and dynamic light scattering (DLS) measurements. A comparison of the micellar parameters usually obtained by these techniques has been carried out. The critical micelle concentrations (CMCs), the geometric packing parameters, the surface excess concentration, the area/surfactant molecule at the interface, the micellar ionization degree β and the free energies of micellization, the diffusion coefficient, and the hydrodynamic diameter were discussed. The effect of added KI on these parameters and on the size and on the kind of aggregates has been also investigated. The addition of 1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE) to the surfactant solutions, where the size of the complex DOPE-surfactant was determined by DLS over a wide range of concentrations, reveals a very different behavior comparing fluorinated and hydrogenated compounds.

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