Study On The Reaction Of BODIPY Derivatives

As a kind of novel fluorescent dyes, BODIPY has a wide range of applications in the field of chemical analysis, environmental monitoring, and chemical biology. Although they are easy to synthesize and own high stability, it still has some drawbacks which we can’t ignore, such as high background fluorescence and poor water-soluble. This research was taking BODIPY as the object, designed and synthesized a series of derivatives. First, synthesized BODIPY 8-position derivatives with different aromatic benzaldehyde (12 compounds) and investigate the influence of reaction by aromatic benzaldehyde; Second, synthesis of 8-chloro-BODIPY by means of phosgene sulfur, and then introduced hetero atom at 8-position by affinity nucleophilic substitution reaction (4 compounds). It utilized the reducibility of 8-bit hetero atoms as specific reactive site; Finally, synthesized chlorinated products (3 compounds) by 2,6-positions electrophilic reaction and get intermediate by formylation, for attaining additional condensation derivatives (3 compounds) which construct reacted site on BODIPY nucleus. The 4-position BF2 center fluorine atoms were substituted to give catechol derivatives (4 compounds).Among the BODIPY derivatives, the one with pyridinium PEBP was only reacted with ONOO- in ethanol. It was demonstrated that 8-position pyridinium structure was destroyed according to characterization. In addition, PEBP only reacted with hypochlorous acid in water. It was confirmed that the product was substituted to get 2,6-chlorine product which was the first fluorescent probe reacted on BODIPY nucleus. PEBP shows excellent water solubility and lower fluorescence quantum yield which could reduce background fluorescence applying on cell imaging. It could be served as a turn-on type fluorescent probe for hypochlorous acid. Since Bodipy 2,6-positions are substituted by chlorine, the electron-withdrawing ability changes dihedral between pyridyl and Bodipy, and then alters the electron density on Bodipy ring which triggered the spectrum redshift and enhancement of fluorescence. In vitro tests, the fluorescence intensity has a good linear relationship with the concentration of sodium hypochlorite which can be used for quantitative detection of sodium hypochlorite. Finally, PEBP could be located at the mitochondria in Hela cells, and detecting concentration changes of hypochlorous acid in the mitochondria.