Ordered nanoassemblies from self‐assembly of amphiphilic molecule containing pillar[5]arene and azobenzene groups

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The derivatization of pillar[ n ]arenes is a prerequisite for endowing them with functions, as well as enriching the application of pillar[ n ]arene materials in advanced material science. Herein, we report the self‐assembly of amphiphilic rim‐differentiated pillar[5]arene ( H 1 ). One side of the pillar[5]arene is composed of hydrophilic poly(ethylene oxide) chains, benzene and azobenzene groups connected with ether bonds, and the other side is composed of ethoxy groups. In CHCl 3 solvent, the amphiphile H 1 self‐assembled into spherical micelles, while in H 2 O/THF mixed solvent H 1 self‐assembled into nanorod‐like assemblies. Interestingly, addition of a guest molecule composed of tetraphenylethene and hexanenitrile groups ( G 1 ) to the CHCl 3 solution of H 1 produces large sheet aggregates via the strong π – π stacking of rod segments. The reversible transformation between the nanosheet assemblies of host–guest complexes and nanoparticles is achieved by addition of the guest molecule 1,4‐butylamine ( G 2 ) and pillar[5]arene with ethoxy groups as competitive molecules. Notably, worm‐like and nanorod micelles of H 1 were constructed in H 2 O/THF solution triggered by light irradiation, which assemblies can be used as photosensitive erasable writing materials.