Self-assembled amphiphilic vesicles based on chiral H8-BINOL to enantioselective recognition of d- and l-phenylalanine

Abstract

Due to the hydrophilicity of furan ring and hydroxyl group, and hydrophobicity of benzene ring and cyclohexyl group, the compounds are easy to form hydrophilic and hydrophobic amphoteric vesicles through self-assembly. The self-assembled vesicles were designed and facilely synthesized using the 2-furanboronic acid and H8-BINOL by Suzuki coupling reaction, which could serve as a novel probe with high enantioselectivity for D/L-Phe. In SEM and TEM images, after adding the L-Phe, the vesicle structure of the H8-BINOL derivatives changed from spherical to dendritic nanotube structures. On the contrary, after the addition of D-Phe, the spherical vesicle structure changed only slightly, indicating that the material had specific recognition for L-Phe. Moreover, the new fluorescent probes had unique rigid structures and obvious enantioselective recognition for phenylalanine in fluorescence testes. In the methanol solution, after adding the L-Phe, the fluorescence intensity of R-1 and S-1 decreased significantly at 368 nm and increased at 306 nm, but D-Phe had no obvious fluorescence effect on the probes, which indicated that the fluorescent probes had a good guiding effect on the recognition of amino acids by chiral compounds.