With the alkyne-functionalised cages in-hand, the synthesis of cage[n]rotaxanes was envisaged using Goldup and co-workers' small 2,2'-bipyridine macrocycle modification of Leigh and co-workers' CuAAC-AMT method with macrocycle M and 3,5-di-tert-butylbenzyl azide, S, as a stopper (Fig. ). Molecular modelling (molecular dynamics in Macromodel, OPLS4 forcefield) of each of the prospective rotaxane structures confirmed a loss in shape-persistency of the cage core on reduction of the imines, as expected, but indicated that the cage framework should be large enough to prevent dethreading of M.