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Article Abstract
Here, we report the synthesis of a family of chiral ZnL tetrahedral cages by subcomponent self-assembly. These cages contain a flexible trialdehyde subcomponent that allows them to adopt stereochemically distinct configurations. The incorporation of enantiopure 1-phenylethylamine produced Δ and Λ enantiopure cages, in contrast to the racemates that resulted from the incorporation of achiral 4-methoxyaniline. The stereochemistry of these ZnL tetrahedra was characterized by X-ray crystallography and chiroptical spectroscopy. Upon binding the enantiopure natural product podocarpic acid, the Zn stereocenters of the enantiopure Δ-ZnL cage retained their Δ handedness. In contrast, the metal stereocenters of the enantiomeric Λ-ZnL cage underwent inversion to a Δ configuration upon encapsulation of the same guest. Insights gained about the stereochemical communication between host and guest enabled the design of a process for acid/base-responsive guest uptake and release, which could be followed by chiroptical spectroscopy.
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| http://dx.doi.org/10.1021/jacs.4c12320 | DOI Listing |
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