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RAS Chemistry & Material ScienceЖурнал органической химии Russian Journal of Organic Chemistry

  • ISSN (Print) 0514-7492
  • ISSN (Online) 3034-6304

SYNTHESIS AND DETECTING PROPERTIES OF NEW LINEAR AND MACROCYCLIC DERIVATIVES OF O,O'-AMINOBENZYLBINOLs

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PII
S30346304S0514749225040062-1
DOI
10.7868/S3034630425040062
Publication type
Article
Status
Published
Authors
A.D. Sergeev
  • Affiliation: Lomonosov Moscow State University, Faculty of Chemistry
A.A. Yakushev
  • Affiliation: Lomonosov Moscow State University, Faculty of Chemistry
A.S. Malyasheva
  • Affiliation: Lomonosov Moscow State University, Faculty of Chemistry
A.D. Averin
  • Affiliation: Lomonosov Moscow State University, Faculty of Chemistry
I.P. Beletskaya
  • Affiliation: Lomonosov Moscow State University, Faculty of Chemistry
Volume/ Edition
Volume 61 / Issue number 4
Pages
404-421
Abstract
A series of O-halobenzyl and O,O’-di(halobenzyl) derivatives of (S)-1,1’-bi(2-naphthol) (BINOL) was synthesized and their catalytic amination using both palladium and copper catalysts was studied. As a result, a new family of BINOLs was obtained which contain various substituents at oxygen atoms with macrocyclic or linear structure, including those with additional chiral centers. The ability of the obtained compounds for detecting metal cations and enantiomers of model amino alcohols was studied by UV and fluorescence titration methods. A potential fluorescent sensor for Al cations was found in a series of linear derivatives due to a multiple increase in the emission; a fluorescent molecular probe for Hg and Al cations was also proposed. Among macrocyclic derivatives, the compound with the longest trioxadiamine linker can be used as a molecular probe for Mg and Ca cations due to the enhancement of fluorescence with a bathofloral shift of the maximum, as well as for Al and Hg cations due to a strong enhancement of fluorescence without changing the position of the emission maximum.
Keywords
БИНОЛ аминирование катализ комплексами палладия и меди макроциклы флуоресценция хиральность детектирование
Date of publication
15.12.2025
Year of publication
2025
Number of purchasers
0
Views
37

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