For our core structure we chose a Tri 2 Di 3 or [2+3] cage design (where for Tri x Di y or [x + y], x = number of tritopic building blocks and y = number of ditopic building blocks in the cage structure), originally reported by Delgado and co-workers. This system was formed through imine condensation between triamine 1 and dialdehyde 2a, followed by reduction to give the robust amine cage C (Fig. ). To incorporate interlocked macrocycle components via CuAAC-AMT, alkyne units were chosen to be installed on the periphery of the structure. To this end, an analogous dialdehyde, 2b, was synthesised incorporating a TIPS-protected alkyne. To allow control over the incorporation of a defined number of mechanically interlocked components, which would enable us to investigate how the extent of functionalisation affected the properties of the cage, we sought to generate POCs with one to three alkyne units on the periphery (C1 to C3, respectively). To achieve this, a scrambled library of DCC cages was generated through the reaction of triamine 1 with a mixture of dialdehydes 2a and 2b in a 3:2:1 ratio (Fig. ). An excess of triamine 1 was used as this has previously been shown to promote conversion to the targeted cages. Figure . Synthesis of alkyne-functionalised cages C1-C3 through imine condensation between triamine 1 and dialdehydes 2, followed by reduction.