Supramolecular
amphiphiles are a type of intriguing building blocks
to fabricate self-assembled nanostructures that can be applied in
diverse fields. Gemini-type supramolecular amphiphiles, containing
two hydrophobic tails and two hydrophilic head groups linked by a
spacer, are good candidates to fabricate many advanced materials that
are able to apply in surface modification, drug/gene delivery, and
solubilization. Pillararenes, the fifth generation of macrocyclic
host molecules, have been used to fabricate many supramolecular amphiphiles
that played important roles in biomedical fields and materials science.
However, compared with single-chain and bola-type supramolecular amphiphiles,
the studies of gemini-type supramolecular amphiphiles based on pillararenes
are very rare. Herein, a new strategy to prepare gemini-type supramolecular
amphiphiles was reported. A new acid-responsive host–guest
recognition motif in water on the basis of a 4,4′-azastilbene
derivative (G1) and a water-soluble pillar[5]arene (WP5) was fabricated. The gemini-type supramolecular amphiphile
was constructed by an azastilbene amphiphilic guest (G2) and WP5. Then its application in stimuli-responsive
self-assemblies was investigated. G2 self-assembled into
nanoribbons in water. Upon addition of WP5, the gemini-type
supramolecular amphiphile formed, leading to the formation of disklike
micelles. After further addition of hydrochloric acid, the morphology
changed into nanosheets.