LAUSR

Borondipyrrins (BODIPYs) have found wide-spread application in bioimaging and material sciences. These applications require the tuning of the chemical and photophysical properties of the fluorophore through the introduction of functional groups at the BODIPY core. In this context, an approach to bisfunctionalized BODIPYs has been explored. The oxidative nucleophilic substitution of hydrogen (ONSH) in the 3-(alpha)-position of BODIPYs has been combined with the nucleophilic substitution (SNAr) at the aryl unit of pentafluorophenyl (PFP)-substituted BODIPYs and their dipyrrane precursors. In an alternative approach, alpha-alkoxy-substituted BODIPYs have been prepared starting from the corresponding dipyrrin. In this case, the alpha-methoxy group of the BODIPY is susceptible to a hitherto unreported methoxy-amino exchange. The compounds were investigated with respect to their optical spectroscopic properties revealing the influence of the different substitution patterns on their absorption and emission spectra.