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Expanding reversible chalcogenide binding: supramolecular receptors for the hydroselenide (HSe) anion

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Abstract

Synthetic supramolecular receptors have been widely used to study reversible solution binding of anions; however, few systems target highly-reactive species. In particular, the hydrochalcogenide anions hydrosulfide (HS) and hydroselenide (HSe) have been largely overlooked despite their critical roles in biological systems. Herein we present the first example of reversible HSe binding in two distinct synthetic supramolecular receptors, using hydrogen bonds from N–H and aromatic C–H moieties. The arylethynyl bisurea scaffold 1tBu achieved a binding affinity of 460 ± 50 M−1 for HSe in 10% DMSO-d6/CD3CN, whereas the tripodal-based receptor 2CF3 achieved a binding affinity of 290 ± 50 M−1 in CD3CN. Association constants were also measured for HS, Cl, and Br, and both receptors favored binding of smaller, more basic anions. These studies contribute to a better understanding of chalcogenide hydrogen bonding and provide insights into further development of probes for the reversible binding, and potential quantification, of HSe and HS.

Graphical abstract: Expanding reversible chalcogenide binding: supramolecular receptors for the hydroselenide (HSe−) anion

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Publication details

The article was received on 06 Sep 2018, accepted on 18 Nov 2018 and first published on 19 Nov 2018


Article type: Edge Article
DOI: 10.1039/C8SC03968B
Citation: Chem. Sci., 2019, Advance Article
  • Open access: Creative Commons BY-NC license
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    Expanding reversible chalcogenide binding: supramolecular receptors for the hydroselenide (HSe) anion

    H. A. Fargher, N. Lau, L. N. Zakharov, M. M. Haley, D. W. Johnson and M. D. Pluth, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C8SC03968B

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