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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

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Abstract

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 CuII, AlIII, CrIII, and InIII cations due to characteristic changes in the fluorescence spectra upon the addition of metal perchlorates.

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Authors and Affiliations

  1. Department of Chemistry, M. V. Lomonosov Moscow State University, 1, Build. 3 Leninskie Gory, 119991, Moscow, Russian Federation

    A. V. Shaferov, A. S. Malysheva, A. D. Averin, O. K. Grigorova & I. P. Beletskaya

  2. A. N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, 31, Build. 4 Leninsky prosp., 119991, Moscow, Russian Federation

    A. D. Averin, A. K. Buryak & I. P. Beletskaya

Authors
  1. A. V. Shaferov
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  2. A. S. Malysheva
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  3. A. D. Averin
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  4. O. K. Grigorova
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  5. A. K. Buryak
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  6. I. P. Beletskaya
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Corresponding author

Correspondence to A. D. Averin.

Additional information

Based on the materials of the XXI Mendeleev Congress on General and Applied Chemistry (September 9–13, 2019, St. Petersburg, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1366–1377, July, 2020.

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Shaferov, A.V., Malysheva, A.S., Averin, A.D. et al. 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. Russ Chem Bull 69, 1366–1377 (2020). https://doi.org/10.1007/s11172-020-2911-7

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  • DOI: https://doi.org/10.1007/s11172-020-2911-7

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