Self-Assembly of Unconventional Low-Molecular-Mass Amphiphiles Containing a PEG Chain

Abstract

The design and synthesis of biocompatible surfactants are important for a wide range of applications in cosmetics, personal care products, and nanomedicine. This feature article summarizes our studies over the past 8 years on the design, synthesis, surface activity, and self-assembly of a series of unconventional low-molecular-mass amphiphiles containing a poly(ethylene glycol) (PEG) tail or spacer and different ionic or zwitterionic headgroups, including carboxylate, sulfonate, and quaternary ammonium salts. Despite having a so-called polar PEG chain as a tail or spacer, these ionic amphiphiles are found to have a tendency to adsorb at the air/water interface and self-assemble in pH 7.0 buffers at 298 K in the same way that conventional hydrocarbon tail surfactants do. However, they are observed to be relatively less surface-active compared to hydrocarbon tail surfactants. Although these amphiphilic molecules have less surface activity, they do self-assemble in aqueous buffer at 298 K, producing a range of microstructures, including spherical micelles, disclike micelles, and vesicles. In fact, our group is the first to report the self-assembly of PEG-tailed ionic amphiphiles in water at room temperature. Some of these molecules are also found to gel various organic liquids on heat-cool treatment or by ultrasound irradiation. We think that the present article will arouse general interest among researchers working toward the development of new biocompatible amphiphiles and soft materials.