Dimeric and Trimeric Catenation of Giant Chiral [8+12] Imine Cubes Driven by Weak Supramolecular Interactions [Data]

Today, the vast majority of catenated structures are built upon macrocycles and only a very few examples of three-dimensional shape-persistent organic cages forming such structures are reported. However, the catenation in all these cases was based on a thermodynamically favoured π-π stacking under certain reaction conditions.

Here, we present our findings that catenane formation can be driven by even less directional dispersion (Keesom) interactions of methoxy-groups during the synthesis of chiral [8+12] imine cubes, giving dimeric and also for the first time trimeric catenated organic cages. To further elucidate the underlying driving forces, eleven differently 1,4-substituted benzene dialdehydes have been reacted with a chiral triamino tribenzotriquinacene under various conditions to study whether monomeric cages or catenated cage dimers are the preferred products.