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 H-1-NMR and ESI-MS. Bioimaging application further demonstrated that probe I would provide a promising method for the detection of hydrogen peroxide in living systems. (C) 2013 Elsevier B.V. All rights reserved.