Chiral BINAM-containing macrocycles with endocyclic 1,8- and 1,5-disubstituted anthraquinone structural fragments

A series of nitrogenand oxygen-containing macrocycles with endocyclic (S)-2,2’-diamino-1,1’-binaphthalene (BINAM) moieties and 1,8or 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.