Supramolecular synthesis is a powerful tool for assembling complex organic molecules, such as macrocycles, cages, catenanes, and molecular knots. However, the targeted design of such molecules can be challenging, especially as the systems become more elaborate, because multi-component assembly reactions have the potential to form a wide range of different species. High-throughput automation can be used to screen a broad synthetic space, but when applied blindly, this approach is inefficient. We have developed a hybrid discovery workflow that fuses computational screening with robotic synthesis for discovering new organic cage molecules, and by extension, other supramolecular assemblies (Figure 1a).<br/><br/>Porous organic cages are a class of self-assembled molecule that contain permanent intrinsic cavities accessible through windows. These molecules can pack together in the solid-state to form interconnected pore networks, making the materials porous. They have shown potential in a number of applications including molecular separations, as sensors, and more recently, in porous liquids – a counter-intuitive new class of porous materials, consisting of a liquid that contains permanent, empty, pores. By fusing our computational toolkit to predict the most likely topology and shape-persistence based on the precursors used, with a robust synthetic route making translation onto an automated synthesis platform possible, the hybrid workflow led to the synthesis of 49 new cages, rapidly accelerating the discovery process. Furthermore, it led to the serendipitous discovery of a unique cage topology – covalently bridged cage catenanes – which could be post-rationalized using further computational modelling. Furthermore, we will introduce how it has been applied in the discovery of a number of other organic materials and supramolecular assemblies, such as completely unsymmetrical porous organic cages, socially self-sorted multi-component cage pots and dumbbells, and porous liquids (Figure 1b).

Hybrid discovery workflow for organic materials and supramolecular self-assemblies

2019 Fall National Meeting

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