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ISSN 1998-9539

Chiral BINAM-Containing Macrocycles with Endocyclic 1,8- and 1,5-Disubstituted Anthraquinone Structural Fragments

Olga K. Grigorova, Alexei D. Averin,@ Olga A. Maloshitskaya, and Irina P. Beletskaya
The article is dedicated to the anniversary of Academician Professor A. Yu. Tsivadze.
Authors cordially congratulate the jubilee and wish him all the best and a plenty of new interesting discoveries!
Lomonosov Moscow State University, Department of Chemistry, 119991 Moscow, Russia
@Corresponding author E-mail: alexaveron@yandex.ru
 
DOI: 10.6060/mhc170937a
Macroheterocycles 2017 10(4-5) 446-453
 
A series of nitrogen- and oxygen-containing macrocycles with endocyclic (S)-2,2’-diamino-1,1’-binaphthalene (BINAM) moieties and 1,8- or 1,5-diaminoanthraquinone chromophores was synthesized using Pd(0)-catalyzed amination with a number of oxadiamines via 2,2’-bis(chloroanthraquinon-1-yl) BINAM derivatives. The dependence of the compounds yields on the structure of starting reagents was established. One exemplary macrocycle was tested as an enantioselective detector for a number of chiral aminoalcohols and 1,2-diphenylethylenediamine and was shown to be able to distinguish between enantiomers of leucinol, 2-amino-1-propanol, 2-amino-1,2-diphenylethanol, and 1,2-diphenylethylenediamine by an increase in the emission in the presence of one enantiomer. It was also shown to detect In(III) among 20 metals tested by emission enhancement.. 

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