Dual‐Rotor Luminescence Based on Supramolecular Secondary Reassembly

Abstract Herein, synergistically confining anthracene‐phenylpyridium derivatives (1’ and 1) as dual‐rotor luminogens through macrocyclic cucurbit[8]uril (CB[8]) and hyaluronic acid (HA) mediated supramolecular secondary reassembly is reported to give bright fluorescence emission. The non‐emissive dual‐rotor molecule 1 first assembles with CB[8] to form non‐emissive supramolecular nanotubes, which are further reconstructed to be nanoparticles with a diameter of 83 nm by HA induced secondary reassembly through electrostatic interaction. Intriguingly, the secondary reassembly not only transforms the topological morphology, but also acts as a switch to activate the robust fluorescence of dual‐rotor molecule, accompanying emission at 600 nm with large Stokes shift (150 nm). This activation is mainly attributed to sufficient suppression of intramolecular rotation and promotion of intramolecular charge transfer of dual‐rotor molecule after reassembly. Benefiting from multiple components synergistic stimuli‐responsiveness and the targeted ability of HA to tumor cells, the secondary reassembly constructed dual‐rotor luminescence system is successfully applied in triplet encryption information security and targeted cancer cell imaging.