Journal
NATURE CHEMISTRY
Volume 5, Issue 4, Pages 276-281Publisher
NATURE PUBLISHING GROUP
DOI: 10.1038/NCHEM.1550
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Funding
- EPSRC [EP/H000925/1]
- Leverhulme Trust [F/00025/Al]
- Royal Society
- Engineering and Physical Sciences Research Council [EP/H000925/1] Funding Source: researchfish
- EPSRC [EP/H000925/1] Funding Source: UKRI
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The energy-efficient separation of chemical feedstocks is a major sustainability challenge. Porous extended frameworks such as zeolites or metal-organic frameworks are one potential solution to this problem. Here, we show that organic molecules, rather than frameworks, can separate other organic molecules by size and shape. A molecular organic cage is shown to separate a common aromatic feedstock (mesitylene) from its structural isomer (4-ethyltoluene) with an unprecedented perfect specificity for the latter. This specificity stems from the structure of the intrinsically porous cage molecule, which is itself synthesized from a derivative of mesitylene. In other words, crystalline organic molecules are used to separate other organic molecules. The specificity is defined by the cage structure alone, so this solid-state 'shape sorting' is, uniquely, mirrored for cage molecules in solution. The behaviour can be understood from a combination of atomistic simulations for individual cage molecules and solid-state molecular dynamics simulations.
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