A highly selective ratiometric fluorescent probe for hydrogen peroxide displaying a large emission shift

A simple water-soluble 4-hydroxynaphthalimide-derived ratiometric fluorescent probe (1) containing a receptor of boronate moiety was designed and synthesized to detect hydrogen peroxide. Probe 1 could quantificationally detect hydrogen peroxide by ratiometric absorption and fluorescence spectroscopy methods with excellent selectivity and sensitivity. Interestingly, probe 1 exhibited 100 nm red-shifted absorption spectra accompanying with the color changes from colorless to yellow-green, and 132 nm red-shifted emission spectra upon addition of hydrogen peroxide. Thus, 1 can serve as a “naked-eye” probe for hydrogen peroxide. Additionally, the reaction mechanism of probe 1 and hydrogen peroxide was confirmed using 1H-NMR and ESI-MS. Bioimaging application further demonstrated that probe 1 would provide a promising method for the detection of hydrogen peroxide in living systems.