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Important biological processes, such as signaling and transport, are regulated by dynamic binding events. The development of artificial supramolecular systems in which binding between different components is controlled could help emulate such processes. Herein, we describe stiff‐stilbene‐containing macrocycles that can be switched between (Z)‐ and (E)‐isomers by light, as demonstrated by UV/Vis and 1H NMR spectroscopy. The (Z)‐isomers can be effectively threaded by pyridinium halide axles to give pseudorotaxane complexes, as confirmed by 1H NMR titration studies and single‐crystal X‐ray crystallography. The overall stability of these complexes can be tuned by varying the templating counteranion. However, upon light‐induced isomerization to the (E)‐isomer, the threading capability is drastically reduced. The axle component, in addition, can form a heterodimeric complex with a secondary isophthalamide host. Therefore, when all components are combined, light irradiation triggers axle exchange between the macrocycle and this secondary host, which has been monitored by 1H NMR spectroscopy and simulated computationally. [ABSTRACT FROM AUTHOR]