Highly specific and sensitive fluorescence detection of hypochlorite in nonbiotic pure water (rapid "turn-on", ~400 fold, λ(em) ~ 560 nm) as well as in living neuronal cell cultures (neutral pH) involves oxidation of a 2-sulfide-2-benzoic acid pendent group in a new meso-thienyl-BODIPY donor-acceptor probe.

Bis-arylsulfide BODIPY systems were prepared and studied for multiple O-atom sensing (at 522 nm); 2- and 3-atom loading was optimal (50-fold, "turn on"). Neuronal studies showed greater H(2)O(2) sensitivity than 2',7'-dichlorofluorescein diacetate. The novel 1,3,6-trimethyl BODIPY formed as a biproduct under Lindsey conditions.

A new BODIPY system displaying an intramolecular π-π-interaction was synthesized and studied. When the selenium center was oxidized, the substituted phenyl group undergoes π-π stacking with one side of the BODIPY core. The oxidized form showed, not only a down-field shift in the NMR peak, but also splitting due to geometrical changes that arise when going from C to C. The compound was characterized by X-ray diffraction; DFT methods helped elucidate the influence of the unexpected π-π stack and its connection to the photophysical properties imparted by the Se oxidation.

We report a refined and expanded synthetic study of 4,4-difluoro-1,3,5,7-tetramethyl-8-(aryl)-4-bora-3a,4a-diaza-s-indacene under treatment with POCl 3 /DMSO. The 2-chloro-6-methylsulfide derivative (Kim TI, Park S, Choi Y and Kim Y. Chem. Asian J. 2011; 6: 1358-61.) was one of five coeluants, including 2,6-disulfido and -dichloro species, and mono-substituted counterparts. The 8-meso tail group modifies product distribution. The different sulfur-containing products undergo different "off-on" responses with NaOCl (10 equiv.). Compounds 4b and 2b exhibit low toxicity and were found to enter juxtanuclear regions in neuroblastoma.

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