The six triamines A-F were each screened against dialdehydes 1-16. Triamine C showed the greatest amount of reactivity towards cage formation, whereas both A and F resulted in no cage topology being observed across all combinations. This follows the lack of literature precedent for A, which has not been reported as a precursor building block in organic cages to the best of our knowledge. However, triamine F has previously been used as a precursor in combination with dialdehyde 2 by Skowronek and coworkers, resulting in the successful formation of an imine Tri 8 Di 12 porous organic cage. In their study, the role of entropy of symmetry as a driving force for cage assembly and structural stability is emphasised. However, the reaction conditions used in this HT screen differ from the reported successful cage synthesis, both in relation to the reaction solvent, temperature, concentration, and reagent stoichiometry, indicating, as expected, that these variables play a contributing role in directing the outcome of the DCC reaction. Each reaction outcome was categorised as follows: single topology observed to form cleanly (dark red) or incompletely (orange); mixture of topologies observed to form cleanly (red) or incompletely (coral); and no topology observed (grey). In (a), the thickness of each connecting line is proportional to the number of precursor combinations leading to each outcome, and the numbers inside or next to each rectangle show the number of precursor combinations assigned to that outcome. In (b), the proportion of outcomes is relative to the total number of reactions a precursor was involved in -the number of total combinations each precursor was in is given on the right. Each triamine precursor was combined with 16 dialdehydes and each trialdehyde was combined with 18 diamines, whereas each dialdehyde was combined with 6 triamines and each diamine was combined with 15 trialdehydes in the precursor library.