Formation of Self-Aggregated Structures of Different Types in Water of Chiral Polymerizable Amphiphiles from l-Tyrosine and l-Phenylalanine

Sodium salts of maleamic acid derivatives from lauryl esters of L-tyrosine (MTNa) and L-phenylalanine (MPNa) were synthesized and characterized. The aggregated structures of MTNa and MPNa in water were investigated, employing several independent methods. MPNa showed secondary aggregated structures in contrast to MTNa at concentrations of >1 × 10(-3) M. The results from dynamic light scattering, transmittance, conductivity, and viscosity measurements suggested the formation of aggregated structures of different types in MTNa and MPNa solutions. The measured fluorescence anisotropy (r) at 0.180 of the fluoroprobe, 1,6-diphenyl-1,3,5-hexatriene (DPH), and the d spacing of 38 Å from small-angle X-ray diffraction (SAXD) experiments confirmed the bilayer structures in MPNa. Scanning electron microscope (SEM) images provided the morphological features. The emulsion produced using MPNa solution was more stable. The confocal fluorescence microscopy image of the emulsion from MPNa confirmed the entrapment of water-soluble dye, rhodamine. The models of MTNa and MPNa molecules and the aggregated structures are presented.