In summary, using a component scrambling methodology following by reduction, we were able to synthesise robust, amine-based organic cages with a defined number of alkyne units on the periphery. These functional handles were able to undergo CuAAC reactions, including AMT to install mechanically interlocked macrocycle components in the formation of [2]-, [3]-and [4]rotaxanes. The presence of the macrocycle components was shown to increase the solubility in CHCl3 of the cage rotaxanes compared to their non-interlocked congeners, as well as modify the thermal properties and gas uptake capability of these materials. More generally, the ability to post-synthetically modify POCs using facile CuAAC chemistry opens the door to readily attaching a range of functional units to the cage scaffolds and prepare functionalised POCs from a common precursor. Ultimately, this will allow the precision engineering of (multi-)functional POCs with customisable properties and behaviours. Studies towards this goal are ongoing in our laboratory.