Phenothiazine and semi-cyanine based colorimetric and fluorescent probes for detection of sulfites in solutions and in living cells

Abstract

Four hemicyanine probes for selectively detecting sulfites (HSO₃⁻/SO₃²⁻) have been constructed by the condensation reaction of 7-substituted (CN, Br, H and OH) phenothiazine aldehyde with 1-ethyl-2,3,3-trimethylindolium iodide. All four probes show a fast and sensitive response to HSO₃⁻/SO₃²⁻ via a Michael addition, with a detection limit lower than 40 nM based on monitoring their UV/vis absorption changes. Although all four probes display an increase in fluorescence when responding to HSO₃⁻/SO₃²⁻, the increment is larger for the probe with an electron-withdrawing group than the probe with an electron-donating group, except for Br. Thus, among four probes the 7-cyano probe (PI-CN) possesses the largest fluorescent response to HSO₃⁻/SO₃²⁻, and the lowest detection limit (7.5 nM). More expediently and easily, a film and a test paper with PI-CN have been prepared to detect HSO₃⁻/SO₃²⁻ in a sample aqueous solution selectively. Finally, the detection of HSO₃⁻/SO₃²⁻ by PI-CN in biological environments has been demonstrated by cell imaging.