Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 45, Pages 24048-24053Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202110442
Keywords
coumarin; fluorescent sensing; halogen bonding; hydrosulfide; anion recognition
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By combining halogen bonding and coumarin fluorophore incorporation in acyclic host structural design, the first XB receptors capable of binding and sensing the hydrosulfide anion in pure water in a reversible chemosensing fashion have been demonstrated. These XB receptors exhibit characteristic selective quenching of fluorescence upon binding to HS-.
Hydrogen sulfide (H2S) 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.
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