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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 under 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 breathing behavior, with completely reversible release and re-uptake of water inside the chiral channel under ambient conditions. Importantly, the HNDPA channel is able to transport water very efficiently and selectively under biomimetic conditions. With a permeability per channel of 3.3 million water molecules per second in large unilamellar vesicles (LUV) and total selectivity against NaCl, the HNDPA channel is a very promising functional nanomaterial for future applications. © 2022 Wiley-VCH GmbH.


Dan G Dumitrescu, Jordi Rull-Barull, Anthony R Martin, Nathalie Masquelez, Maurizio Polentarutti, Annie Heroux, Nicola Demitri, Giorgio Bais, Ionut-Tudor Moraru, Romuald Poteau, Muriel Amblard, Andraž Krajnc, Gregor Mali, Yves-Marie Legrand, Arie van der Lee, Baptiste Legrand. The Unexpected Helical Supramolecular Assembly of a Simple Achiral Acetamide Tecton Generates Selective Water Channels. Chemistry (Weinheim an der Bergstrasse, Germany). 2022 Jun 10;28(33):e202200383

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PMID: 35420228

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