Naphthalene peri-Diselenide-Based BODIPY Probe for the Detection of Hydrogen Peroxide, tert-Butylhydroperoxide, Hydroxyl Radical, and Peroxynitrite Ion.

Dimethoxynaphthalene peri-diselenide-based BODIPY (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) probe has been synthesized. The probe demonstrated selectivity and sensitivity for hydrogen peroxide (H(2)O(2)) and tert-butylhydroperoxide (t-BuOOH), hydroxyl radical ((•)OH), and peroxynitrite ion (ONOO(-)) detection and reversibility upon treatment with glutathione. The limits of detection of the probe were observed to be 0.40 μM for H(2)O(2), 0.41 μM for t-BuOOH, 0.95 μM for (•)OH, and 0.46 μM for ONOO(-), respectively. A proposed mechanism for the "turn-on" event has been suggested and corroborated by spectroscopic and computational data. It has been proposed that electron transfer occurred from the Se center to the BODIPY moiety, followed by the photoinduced electron transfer (PET) mechanism.