A multifunctional supramolecular assembly was successfully constructed by the host-guest complexation of doubly positively charged adamantane (ADA) with β-CD-modified hexabenzocoronene and the π-stacking of coronene with mitoxantrone, which was characterized by transmission electron microscopy, scanning electron microscopy, dynamic light-scattering, and zeta potential experiments. Possessing a small size and rigid backbone coronene center, the water-soluble biocompatible supramolecular assembly has intracellular imaging abilities. Moreover, after the ester group of ADA was hydrolyzed into a carboxyl group, the positively charged quaternary amine strand converted into a zwitterion structure, which realized the controlled plasmid DNA binding and release.
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