Hypochlorite-Mediated Modulation of Photoinduced Electron Transfer in a Phenothiazine-Boron dipyrromethene Electron Donor-Acceptor Dyad: A Highly Water Soluble Turn-On Fluorescent Probe for Hypochlorite

A highly water-soluble phenothiazine (PTZ)-boron dipyrromethene (BODIPY)-based electron donor-acceptor dyad (WS-Probe), which contains BODIPY as the signaling antennae and PTZ as the OCl- reactive group, was designed and used as a fluorescent chemosensor for the detection of OCl-. Upon addition of incremental amounts of NaOCl, the quenched fluorescence of WS-Probe was enhanced drastically, which indicated the inhibition of reductive photoinduced electron transfer (PET) from PTZ to (BODIPY)-B-1*; the detection limit was calculated to be 26.7nm. Selectivity studies with various reactive oxygen species, cations, and anions revealed that WS-Probe was able to detect OCl- selectively. Steady-state fluorescence studies performed at varied pH suggested that WS-Probe can detect NaOCl and exhibits maximum fluorescence in the pH range of 7 to 8, similar to physiological conditions. ESI-MS analysis and (HNMR)-H-1 spectroscopy titrations showed the formation of sulfoxide as the major oxidized product upon addition of hypochlorite. More interestingly, when WS-Probe was treated with real water samples, the fluorescence response was clearly visible with tap water and disinfectant, which indicated the presence of OCl- in these samples. The in vitro cell viability assay performed with human embryonic kidney 293 (HEK293) cells suggested that WS-probe is non-toxic up to 10m and implicates the use of the probe for biological applications.