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Reversible switching between the closed cyclic dimeric assembly [Cu 2 ( 1 ) 2 ] 2+  (OFF state) and the extended dimeric homoleptic complex [FeCu 2 ( 1 ) 2 ] 4+  (ON State) by addition/removal of Fe 2+  triggered catalysis of a double‐click reaction and high yield preparation of [2]rotaxanes. Mechanistic and computational studies provide valuable general insight for double‐click strategies by revealing cooperative effects in the second cycloaddition step due to a distance‐tolerant preorganization of the first‐click product by the two copper(I)‐loaded phenanthroline subunits of [FeCu 2 ( 1 ) 2 ] 4+ .

Cooperative Effects in Switchable Catalysis: Enhancing Double‐Click Reaction Yield of Symmetrical Rotaxanes