Hydrosulfide (HS- ) Recognition and Sensing in Water by Halogen Bonding Hosts

Edward J Mitchell; Adam J Beecroft; Jonathan Martin; Sally Thompson; Igor Marques; Vítor Félix; Paul D Beer

doi:10.1002/anie.202110442

Hydrosulfide (HS^- ) Recognition and Sensing in Water by Halogen Bonding Hosts

Angew Chem Int Ed Engl. 2021 Nov 2;60(45):24048-24053. doi: 10.1002/anie.202110442. Epub 2021 Oct 5.

Authors

Edward J Mitchell¹, Adam J Beecroft¹, Jonathan Martin², Sally Thompson², Igor Marques³, Vítor Félix³, Paul D Beer¹

Affiliations

¹ Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK.
² Radioactive Waste Management, Building 329, Thomson Avenue, Harwell Campus, Didcot, OX11 0GD, UK.
³ CICECO-Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, 3810-193, Aveiro, Portugal.

Abstract

Hydrogen sulfide (H₂ S) plays a crucial signalling role in a variety of physiological systems, existing as the hydrosulfide anion (HS^- ) at physiological pH. Combining the potency of halogen bonding (XB) for anion recognition in water with coumarin fluorophore incorporation in acyclic host structural design, the first XB receptors to bind and, more importantly, sense the hydrosulfide anion in pure water in a reversible chemosensing fashion are demonstrated. The XB receptors exhibit characteristic selective quenching of fluorescence upon binding to HS^- . Computational DFT and molecular dynamics simulations in water corroborate the experimental anion binding observations, revealing the mode and nature of HS^- recognition by the XB receptors.

Keywords: anion recognition; coumarin; fluorescent sensing; halogen bonding; hydrosulfide.

Publication types

Research Support, Non-U.S. Gov't