Trapping hydrogen sulfide (H₂S) with diselenides: the application in the design of fluorescent probes

Org Lett. 2015 Mar 20;17(6):1541-4. doi: 10.1021/acs.orglett.5b00431. Epub 2015 Feb 27.

Abstract

Here we report a unique reaction between phenyl diselenide-ester substrates and H2S to form 1,2-benzothiaselenol-3-one. This reaction proceeded rapidly under mild conditions. Thiols could also react with the diselenide substrates. However, the resulted S-Se intermediate retained high reactivity toward H2S and eventually led to the same cyclized product 1,2-benzothiaselenol-3-one. Based on this reaction two fluorescent probes were developed and showed high selectivity and sensitivity for H2S. The presence of thiols was found not to interfere with the detection process.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Fluorescent Dyes / chemical synthesis*
  • Fluorescent Dyes / chemistry
  • Hydrogen Sulfide / chemistry*
  • Molecular Structure
  • Organoselenium Compounds / chemical synthesis*
  • Organoselenium Compounds / chemistry
  • Sulfhydryl Compounds / chemistry

Substances

  • 1,2-benzothiaselenol-3-one
  • Fluorescent Dyes
  • Organoselenium Compounds
  • Sulfhydryl Compounds
  • Hydrogen Sulfide