Steric Hindrance in Metal Coordination Drives the Separation of Pyridine Regioisomers Using Rhodium(II)‐Based Metal–Organic Polyhedra
2021
The physicochemical similarity of isomers makes their chemical separation through conventional techniques energy intensive. Herein, we report that, instead of using traditional encapsulation-driven processes, steric hindrance in metal coordination on the outer surface of Rh(II)-Based Metal Organic Polyhedra (Rh-MOPs) can be used to separate pyridine-based regioisomers via liquid-liquid extraction. Through molecular dynamics simulations and wet experiments, we discovered that the capacity of pyridines to coordinatively bind to Rh-MOPs is determined by the positions of the pyridine substituents relative to the pyridine nitrogen and is influenced by steric hindrance. Thus, we exploited the differential solubility of bound and non-bound pyridine regioisomers to engineer liquid-liquid self-sorting systems. As proof-of-concept, we separated four different equimolecular mixtures of regioisomers, including a mixture of the industrially-relevant compounds 2-chloropyridine and 3-chloropyridine, isolating highly pure compounds in all cases.
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