The imine cages were then reduced in situ to form a mixture of amine organic cages that could be separated by column chromatography, yielding the cages C1 TIPS and C2 TIPS in 20% and 14% isolated yield, respectively. Removal of the TIPS protecting groups furnished the terminal alkyne-functionalised cages, C1 and C2, with one and two alkyne units, respectively. The tri-alkyne cage C3 was directly synthesised using three equivalents of dialdehyde 2b and triamine 1, followed by reduction and deprotection, in 41% overall yield. The successful synthesis of each of C1-C3 was confirmed by high-resolution electrospray ionisation mass spectrometry (HR-ESI-MS) and NMR spectroscopy.