Calix[2]azolium[2]benzimidazolone hosts for selective binding of neutral substrates in water

Sha Bai, Lu-Wen Zhang, Zi-Hang Wei, Fang Wang, Qing-Wen Zhu and Ying-Feng Han ()
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Sha Bai: Northwest University
Lu-Wen Zhang: Northwest University
Zi-Hang Wei: Northwest University
Fang Wang: Northwest University
Qing-Wen Zhu: Northwest University
Ying-Feng Han: Northwest University

Nature Communications, 2024, vol. 15, issue 1, 1-10

Abstract: Abstract The separation and purification of chemical raw materials, particularly neutral compounds with similar physical and chemical properties, represents an ongoing challenge. In this study, we introduce a class of water-soluble macrocycle compound, calix[2]azolium[2]benzimidazolone (H), comprising two azolium and two benzimidazolone subunits. The heterocycle subunits form a hydrophobic binding pocket that enables H1 to encapsulate a series of neutral guests in water with 1:1 or 2:1 stoichiometry, including aldehydes, ketones, and nitrile compounds. The host-guest complexation in the solid state was further confirmed through X-ray crystallography. Remarkably, H1 was shown to be a nonporous adaptive crystal material to separate valeraldehyde from the mixture of valeraldehyde/2-methylbutanal/pentanol with high selectivity and recyclability in the solid states. This work not only demonstrates that azolium-based macrocycles are promising candidates for the encapsulation of organic molecules but also shows the potential application in separation science.

Date: 2024
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DOI: 10.1038/s41467-024-50980-z

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