Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

Design Principles for the Optimization of Guest Binding in Aromatic-Paneled FeII4L6 Cages

Design Principles for the Optimization of Guest Binding in Aromatic-Paneled FeII4L6 Cages
Jonathan R. Nitschke, Wenjing Meng, Tanya K. Ronson
A series of aromatic-paneled FeII4L6 cages was synthesized through iron(II)-templated subcomponent self-assembly of 2-formylpyridine and C2-symmetric diamine building blocks having differing geometries, including many with a large degree of lateral offset between metal-binding sites. The new cages were characterized using X-ray crystallography, NMR spectroscopy, and mass spectrometry. Investigations of the guest binding properties of the cages provided insights into the structural factors important for the observation of guest binding. Both the size and arrangement of the aromatic panels were shown to be crucial for achieving effective encapsulation of large hydrophobic guests, including fullerenes, polycyclic aromatic hydrocarbons, and steroids, with subtle differences in the structure of subcomponents resulting in incommensurate effects on the binding abilities of the resulting hosts. Cages with large, offset aromatic panels were observed to be the most effective hosts as a result of a preference for a ligand conformation where the aromatic panels lie tangent to the edges of the tetrahedron, thus maximizing cavity enclosure.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b05202

DOI: 10.1021/jacs.7b05202

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