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Article Dans Une Revue Chemistry - A European Journal Année : 2022

The Unexpected Helical Supramolecular Assembly of a Simple Achiral Acetamide Tecton Generates Selective Water Channels

Dan Dumitrescu
Nicola Demitri
Gregor Mali

Résumé

Achiral 2-hydroxy-N-(diphenylmethyl)acetamide (HNDPA) crystallizes in the P61 chiral space group as a hydrate, building up permeable chiral crystalline helical water channels. The crystallization driven chiral self-resolution process is highly robust, with the same air stable crystalline form readily obtained from a variety of conditions. Interestingly, the HNDPA supramolecular helix inner pore is filled by a helical water wire. The whole edifice is mainly stabilized by robust hydrogen bonds involving the HNDPA amide bonds and CH…π interactions between the HNDPA phenyl groups. The crystalline structure shows a breathing behavior, with completely reversible release and reuptake of water inside the chiral channel, under ambient conditions. Importantly, the HNDPA channel is able to transport water very efficiently and selectively in biomimetic conditions. With a permeability per channel of 3.3 million water molecules per second in large unilamellar vesicles (LUV) and a total selectivity against NaCl, the HNDPA channel is a very promising functional nanomaterial for future applications.

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Chimie organique
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Origine : Publication financée par une institution
Licence : CC BY - Paternité

Dates et versions

hal-03643372 , version 1 (15-04-2022)
hal-03643372 , version 2 (21-10-2022)

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Paternité

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Dan Dumitrescu, Jordi Rull-Barull, Anthony R. Martin, Nathalie Masquelez, Maurizio Polentarutti, et al.. The Unexpected Helical Supramolecular Assembly of a Simple Achiral Acetamide Tecton Generates Selective Water Channels. Chemistry - A European Journal, 2022, 28 (33), pp.e202200383. ⟨10.1002/chem.202200383⟩. ⟨hal-03643372v2⟩
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