Abstract
We define a nomenclature for the classification of porous organic cage molecules, enumerating the 20 most probable topologies, 12 of which have been synthetically realised to date. We then discuss the computational challenges encountered when trying to predict the most likely topological outcomes from dynamic covalent chemistry (DCC) reactions of organic building blocks. This allows us to explore the extent to which comparing the internal energies of possible reaction outcomes is successful in predicting the topology for a series of 10 different building block combinations.
Highlights
Molecular design is the perpetual ambition of chemists as they strive for more complex and unusual molecular assemblies, both for their inherent beauty and to encode more sophisticated functions
For the tritopic + ditopic family, we investigated the outcome of combining 1,3,5-triformylbenzene (1 in Fig. 15) and (R,R)1,2-diaminocyclohexane (2 in Fig. 15), used in the synthesis of CC3, a Tri4Di6 imine molecule.[27,80]
We have enumerated the 20 possible topologies that can be used as underlying structures for the design and the synthesis
Summary
Molecular design is the perpetual ambition of chemists as they strive for more complex and unusual molecular assemblies, both for their inherent beauty and to encode more sophisticated functions These assemblies include both network materials, such as metal–organic frameworks (MOFs), and discrete molecular architectures that are of the nanometre scale. A wide range of different motifs have been realised, including rings, cycles, knots, polyhedra and catenanes.[7,8,9] Here we focus upon molecular cage compounds, defined by IUPAC as polycyclic compounds with the shape of a cage These have the potential to host other molecules inside their internal cavity, but, unlike macrocycles, have three dimensional structures with multiple possible entry and exit routes through molecular windows. Potential applications for these molecular hosts include encapsulation,[17] catalysis,[18] molecular separations of organic molecules[19,20] or gases,[21,22] molecular sensing,[23,24] molecular reaction vessels, or as porous liquids.[25]
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