ИСТИНА

The development of fluorescent enantioselective detectors is highly demanded by a need to elaborate simple, efficient and veritable methods of identification of enantiomers as their role in modern chemistry and industry has been steadily increasing. We developed a general method for the synthesis of macrocycles 4 comprising an endocyclic C2-chiral structural fragment of 2,2’-diamino-1,1’-binaphthalene (BINAM) which also possesses useful fluorescent properties [1]. These macrocycles can be easily synthesized in two steps using Pd(0)-catalyzed amination reactions from (S)-BINAM 1 via N,N’-di(3-bromophenyl)derivatives 2. Further these compounds were modified with 3-bromobenzyl substituents and macrocycles 5 were introduced in the Pd(0)-catalyzed amination with chiral amines to give macrocycles 6 and 9 possessing chiral podand groups. These molecules were decorated with exocyclic strong fluorophore groups like dansyl and 7-methoxycoumarine which contain additional coordination site. The resulting compounds 6-10 were investigated as fluorescent enantioselective detectors for a series of optically pure amino alcohols.