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Title

Anion Transport with Pnictogen Bonds in Direct Comparison with Chalcogen and Halogen Bonds
Authors
Lee, Lucia M.
Tsemperouli, Maria
Poblador Bahamonde, Amalia Isabel
Benz, Sebastian
Sakai, Naomi
Sugihara, Kaori
Matile, Stefan
Published in Journal of the American Chemical Society. 2019, vol. 141, no. 2, p. 810-814
Abstract In this Communication, we introduce transmembrane anion transport with pnictogen-bonding compounds and compare their characteristics with chalcogen- and halogen-bonding analogues. Tellurium-centered chalcogen bonds are at least as active as antimony-centered pnictogen bonds, whereas iodine-centered halogen bonds are 3 orders of magnitude less active. Irregular voltage-dependent single-channel currents, high gating charges, and efficient dye leakage support for the formation of bulky, membrane-disruptive supramolecular amphiphiles due to “too strong” binding of anions to tris(perfluorophenyl)stibanes. In contrast, the chalcogen-bonding bis(perfluorophenyl)tellanes do not cause leakage and excel as carriers with nanomolar activity, with P(Cl/Na) = 10.4 for anion/cation selectivity and P(Cl/NO3) = 4.5 for anion selectivity. The selectivities are lower with pnictogen-bonding carriers because their membrane-disturbing 3D structure also affects weaker binders (P(Cl/Na) = 2.1, P(Cl/NO3) = 2.5). Their 2D structure, directionality, hydrophobicity, and support from proximal anion−π interactions are suggested to contribute to the unique power of chalcogen bonds to transport anions across lipid bilayer membranes.
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Article (Accepted version) (1.3 MB) - public document Free access
Other version: http://pubs.acs.org/doi/10.1021/jacs.8b12554
Structures
Faculté des sciences / Section de chimie et biochimie / Département de chimie physique
Faculté des sciences / Section de chimie et biochimie / Département de chimie organique
Research groups Groupe Matile
Groupe Sugihara
Citation
(ISO format) 		LEE, Lucia M. et al. Anion Transport with Pnictogen Bonds in Direct Comparison with Chalcogen and Halogen Bonds. In: Journal of the American Chemical Society, 2019, vol. 141, n° 2, p. 810-814. doi: 10.1021/jacs.8b12554 https://archive-ouverte.unige.ch/unige:113057

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Deposited on : 2019-01-18

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