Issue 1, 2019

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
06 Sep 2018
Accepted
18 Nov 2018
First published
19 Nov 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2019,10, 67-72

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, 10, 67 DOI: 10.1039/C8SC03968B

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