A Novel pH-Sensitive Chiral Amphiphile: Synthesis, Aggregation, and Interaction with β-Cyclodextrin

Abstract

A novel pH-sensitive chiral amphiphile, N-(4-decyloxy-2- hydroxybenzylidene)-l-leucine, was synthesized. Two kinds of vesicles were found at different pH ranges, 6.5−8.0 and 11.5−12.5, and a helical structure was observed at pH = 11.0. This unique behavior can be attributed to the formation of a dimeric structure. The interaction between this amphiphile and β-cyclodextrin was investigated by fluorescence emission spectra, 1H NMR, and molecular modeling.