pH-Dependent Si-Fluorescein Hypochlorous Acid Fluorescent Probe: Spirocycle Ring-Opening and Excess Hypochlorous Acid-Induced Chlorination

  • 10.1021/ja401426s
  • Journal of the American Chemical Society
  • p 13365-13370, Volume 135, Issue 36,
  • journal-article
We report the synthesis and characterization of a fluorescent probe (Hypo-SiF) designed for the detection of hypochlorous acid (HOCl) using a silicon analogue of fluorescein (SiF). The probe is regulated in an “off–on” fashion by a highly selective thioether spirocyclic nonfluorescent structure that opens to form a mixture of fluorescent products in the presence of HOCl. Over a range of pH values, the probe reacts with a stoichiometric amount of HOCl, resulting in a mixture of two pH-dependent fluorescent species, a SiF disulfide product and a SiF sulfonate product. The unique colorimetric properties of the individual SiF fluorophores were utilized to perform simultaneous detection of HOCl and pH. When an excess of HOCl is present, the SiF fluorophores become chlorinated, via an intermediate halohydrin, resulting in a more pH independent and red-shifted fluorophore.


Novel and less expensive Hypo-SiF synthesis

  • Hypo-SiF is uniquely new in finding the high concentration of HOCl
  • Hypo-SiF is reported to be good in finding the HOCl concentration and pH of the media simultaneously at lower concentrtion
  • To obtain clear results, Hypo-SiF needs to be improved and thorough analysis of...