Triply interlocked covalent organic cages
Author: ["Tom Hasell","Xiaofeng Wu","James T. A. Jones","John Bacsa","Alexander Steiner","Tamoghna Mitra","Abbie Trewin","Dave J. Adams","Andrew I. Cooper"]
Publication: Nature Chemistry
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Abstract
Interlocked molecules comprise two or more separate components that are joined by ‘mechanical’ rather than covalent bonds. In other words, these molecular assemblies cannot be dissociated without the cleavage of one or more chemical bonds. Although recent progress has enabled the preparation of such topologies through coordination or templating interactions, three-dimensional interlocked covalent architectures remain difficult to prepare. Here, we present a template-free one-pot synthesis of triply interlocked organic cages. These 20-component dimers consist of two tetrahedral monomeric cages each built from four nodes and six linkers. The monomers exhibit axial chirality, which is recognized by their partner cage during the template-free interlocking assembly process. The dimeric cages also include two well-defined cavities per assembly, which for one of the systems studied led to the formation of a supramolecular host–guest chain. These interlocked organic molecules may prove useful as part of a toolkit for the modular construction of complex porous solids and other supramolecular assemblies. Interlocked molecules commonly include one (or more) monocyclic component — examples comprising bicyclic or tricyclic structures are much more rare and usually involve metal–ligand coordination or additional templates. Now, the dynamic self-assembly of twenty organic molecules in a one-pot synthesis has been shown to produce tetrahedral covalent cages, which interpenetrate during the process to form triply interlocked dimers.
Cite this article
Hasell, T., Wu, X., Jones, J. et al. Triply interlocked covalent organic cages. Nature Chem 2, 750–755 (2010). https://doi.org/10.1038/nchem.739
