Yang, Yuchong; Ronson, Tanya K; Hou, Dingyu; Luo, Kai H; Nitschke, Jonathan R; (2025) Fluoride Enhances Alcohol Binding Within a Trigonal-Prismatic Metal-Organic Capsule. Angewandte Chemie International Edition , 64 (29) , Article e202505137. 10.1002/anie.202505137.

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Abstract

Herein we utilize the binding of fluoride to boron atoms to functionalize the interior of a boron-containing trigonal prismatic capsule that incorporates two triangular and three rectangular ligands, enabling the tuning of its guest binding properties. The methyl groups of the triangular ligands guide the rectangular ligands to adopt a “landscape” orientation to avoid steric hindrance. This small structural change gives rise to an enlarged interior cavity volume for guest encapsulation, as compared with a previously-reported trigonal prismatic capsule, where the same rectangular ligand took a “portrait” orientation with a non-methylated triangular ligand of similar size. The methylated triangular ligand contains a boron core, which can bind fluoride ions that point inward. These bound fluorides serve as hydrogen bond acceptors, which increases the affinity of the capsule for hydrogen-bond-donating alcohols, which are bound in preference to ketones of similar sizes. Moreover, this boron-containing trigonal prism selectively binds perrhenate over perchlorate, while fluoride binding modulates the cavity charge, leading to perrhenate ejection. These and similar endo-functionalized capsules may thus be of use in the fields of molecular recognition and separation.

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