Metal coordination to a deep cavitand promotes binding selectivities in water

One goal of supramolecular chemistry is the creation of synthetic receptors that have a high affinity for hydrophilic molecules in water. We found that cavitands with upper rims extended by pyridyl groups coax hydrophilic guests into the cavity where they are shielded from the aqueous environment. T...

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Bibliographic Details
Published in:Chinese chemical letters 2022-11, Vol.33 (11), p.4908-4911
Main Authors: Chen, Yong-Qing, Guan, Hua-Wei, Kanagaraj, Kuppusamy, Rebek, Julius, Yu, Yang
Format: Article
Language:English
Subjects:
Host-guest chemistry
Hydrophilic small molecules
Metallo cavitand
Molecular recognition
Water-soluble containers
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Summary:One goal of supramolecular chemistry is the creation of synthetic receptors that have a high affinity for hydrophilic molecules in water. We found that cavitands with upper rims extended by pyridyl groups coax hydrophilic guests into the cavity where they are shielded from the aqueous environment. The ability of Pd(II) to coordinate adjacent pyridyl groups leads to increased selectivity for highly hydrophilic solvent molecules such as acetone, 1,4-dioxane and tetrahydrofuran in water. Analysis of the binding behavior indicated that metal-coordination restricts the container entrance, shrinks the effective cavity volume and increases the energetic barrier to guest exchange. Water-soluble cavitands with pyridyl rims coordinate to Pd(II) and confine hydrophilic solvent molecules such as acetone, 1,4-dioxane and tetrahydrofuran. [Display omitted]
ISSN:1001-8417
1878-5964
DOI:10.1016/j.cclet.2022.03.039