Synthesis of optically active 3,3’-disubstituted biphenyl derivatives using palladium-catalyzed amination and their evaluation as enantioselective fluorescent detectors for amino alcohols and metal cations

The palladium-catalyzed amination was used to synthesize optically active 3,3’-diaminosubstituted biphenyl derivatives (in particular, macrocyclic derivatives) decorated with additional fluorophore groups (dansyl and 7-methoxycoumarin). The synthesized compounds were studied by spectroscopic methods (UV spectroscopy, fluorescence) in the presence of individual enantiomers of amino alcohols and metal salts. One of the synthesized compounds was demonstrated to serve as an enantioselective fluorescent detector for enantiomers of 2-amino-1-propanol because of different changes in the fluorescence spectra. Certain compounds can be used as molecular probes for the detection of Cu, Al, Cr, and In cations due to characteristic changes in the fluorescence spectra upon the addition of metal perchlorates.