Synthesis of optically active 2,7-disubstituted naphthalene derivatives and evaluation of their enantioselective recognition ability

Abstract

The palladium-catalyzed amination was used to synthesize 2,7-diamino derivatives of naphthalene containing two chiral substituents and fl uorophore groups (dansyl, 7-methoxycoumarin, 6,7-dimethoxycoumarin, 6-aminoquinoline). The synthesized compounds were studied by UV absorption and fl uorescence spectroscopy in the presence of individual enantiomers of amino alcohols and salts of 21 metals. The possibility of using these compounds as fl uorescent detectors for optically active compounds and metals was examined. In the presence of (S)-leucinol, the diquinoline derivative showed enhanced emission with a maximum at shorter wavelengths, which is not typical of its (R) isomer. This fact can be used for the recognition of these enantiomers. A number of naphthalene derivatives can be considered as potential fl uorescent chemosensors for Cu II cations due to the total fl uorescence quenching in the presence of this metal.