In this work, we present the synthesis of organic cage[n]rotaxanes by exploiting the copper(I)-catalysed azidealkyne cycloaddition (CuAAC) active metal template (AMT) approach. Using this method, we were able to mechanically append macrocyclic components to peripherally functionalise organic cages with unoccupied cavities. Subsequent investigations into the differences in physiochemical properties between the interlocked and noninterlocked species demonstrated the potential for using the mechanical bond to modify the behaviour of these discrete systems.