Dynamic Regulation of Supramolecular Chirality in an Amphiphilic Dimeric Macrocycle Through Azobenzene‐Based Photoisomerization

]paracyclophane, preserves orthogonal host-guest properties while exhibiting unique amphiphilicity-directed self-assembly behavior. Under UV irradiation, trans-to-cis isomerization of an alanine-substituted azobenzene guest induces stereoselective binding modes, which dynamically modulate the planar chirality and morphologies of m-TPE WP5-PCP. Subsequent removal of the UV stimulus reverses the isomerization process, leading to the reformation of threaded complexes and the restoration of chiral supramolecular assemblies. This process demonstrates hierarchical regulation of supramolecular handedness via orthogonal molecular recognition pathways. The proposed strategy effectively integrates supramolecular chirality switching with stimuli-responsive energy transduction, offering new avenues for the development of adaptive nanomaterials.