Figure (Top) High-throughput experimental workflow, including the setup on the automated liquidhandling OT-2 platform. Rapid parallel solvent evaporation was achieved using an EquaVAP, and the sample preparation for characterisation was undertaken on the OT-2 prior to HT measurements being carried out. (Middle) High-throughput experimental data (turbidity, 1 H NMR and high-resolution mass spectrometry) was automatically analysed to assign the reaction outcomes of the 366 imine condensations by species type, conversion, topological outcome, and in combination with the HT computational data (pore size analysis) led to the range of successfully formed organic cages being narrowed down further to identify shape-persistent POCs. (Bottom) High-throughput computational workflow for the optimisation and loading of each precursor building block, followed by the assembly into organic cages of the four most common topologies (