Synthesis of optically active 2,7-disubstituted naphthalene derivatives and evaluation of their enantioselective recogni
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Synthesis of optically active 2,7-disubstituted naphthalene derivatives and evaluation of their enantioselective recognition ability* A. S. Malysheva,a A. V. Shaferov,a A. D. Averin,a,b O. K. Grigorova,a O. A. Maloshitskaya,a V. A. Roznyatovsky,a and I. P. Beletskayaa,b aDepartment
of Chemistry, M. V. Lomonosov Moscow State University, 1, Build. 3 Leninskie Gory, 119991 Moscow, Russian Federation. Fax: +7 (495) 939 3618. E-mail: [email protected] bA. N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, 31, Build. 4 Leninsky prosp., 119991 Moscow, Russian Federation The palladium-catalyzed amination was used to synthesize 2,7-diamino derivatives of naphthalene containing two chiral substituents and fluorophore groups (dansyl, 7-methoxycoumarin, 6,7-dimethoxycoumarin, 6-aminoquinoline). The synthesized compounds were studied by UV absorption and fluorescence spectroscopy in the presence of individual enantiomers of amino alcohols and salts of 21 metals. The possibility of using these compounds as fluorescent 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 fluorescent chemosensors for CuII cations due to the total fluorescence quenching in the presence of this metal. Key words: naphthalene, amination, palladium catalysis, chirality, fluorescence, detection.
The aromatic naphthalene moiety is successfully employed as one of the simplest fluorophore groups involved in fluorescent chemosensors for the recognition of metal cations, in particular zinc.1,2 Naphthalene is also widely utilized as a signaling fluorophore in enantioselective detectors capable of recognizing enantiomers of optically active compounds. For example, chiral thiourea derivatives containing an 1-aminonaphthyl moiety proved to be able to detect the L- and D-aspartate, L- and D-glutamate, and L- and D-tartrate enantiomers (as tetramethylammonium salts).3,4 A similar compound, a chiral urea derivative, was described in the study.5 Macrocyclic compounds containing a 1,4-disubstituted naphthalene moiety as a spacer and bearing two chiral centers in the macrocycle also proved to be efficient in recognizing a number of amino acids.6 Calix[4]arenes functionalized at the upper rim with chiral substituents containing 2-oxynaphthalene groups were used for the detection of isomers of mandelic acid.7 A modification of calixarenes at the lower rim by including four 1-oxynaphthalene units as substituents was demonstrated to be efficient for the identification of phenylalaninol enantiomers.8 A chemosensor based on a NiII * Based on the materials of the XXI Mendeleev Congress on General and Applied Chemistry (September 9—13, 2019, St. Petersburg, Russia).
complex as a receptor and containing the signaling naphthalene moi
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