Inspired by the natural phospholipid bilayer nanostructure, which is an important part of the cell membrane, various functional groups were introduced into pillararene-based macrocyclic amphiphiles, endowing their self-assemblies with interesting applications. For example, we designed and synthesized an amphiphilic pillar[5]arene containing five amino groups as the hydrophilic head and five alkyl chains as the hydrophobic tail. It self-assembled into well-defined nanovesicles under neutral conditions in 1 minute, and gradually transformed into microtubes after standing for 4 months. The nanovesicles were used in the controlled release of small molecules and the microtubes could be used to adsorb TNT. Similarly, “sweet nanotubes” were obtained from self-assembly of a sugar-functionalized macrocyclic amphiphile. These nanotubes were utilized as excellent cell glues to agglutinate and inhibit the motility of pathogenic cells E. coli.<br/>Pillararene-based host-guest interactions were employed to construct a series of supra-amphiphiles not only in organic solvent but also in water. For example, we constructed a novel supramolecular amphiphile based on a pillar[6]arene and an azobenzene-containing guest in an organic solvent, which underwent a photoresponsive threading-dethreading switch upon UV and visible light irradiation due to the trans−cis photoisomerization of the guest, accompanied by disassembly and assembly of the corresponding aggregates.

Nanostructures prepared from self-assembly of pillararene-based amphiphiles and supra-amphiphiles

251st National Meeting (2016)

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