ИСТИНА

Our approach to chiral fluorescent chemosensors is based on the combination of macrocyclic receptor unit with the endocyclic C2-chiral 2,2’-diamino-1,1’-binaphthalene (BINAM) moiety which simultaneously can serve as a fluorophore group. The modification of sensing and coordination properties of such macrocycles can be achieved by the introduction of additional exocyclic fluorophores like dansyl, quinoline or methoxycoumarin. Various macrocycles with phenylene, naphthalene or anthraquinone spacers and oxadiamine linkers were synthesized using Pd-catalyzed amination reactions. Chiral macrobicyclic cryptands were obtained by the reactions of bis(bromobenzyl)substituted diazacrown ethers, cyclen or cyclam with free BINAM. The macrocycles thus obtained were tested as fluorescent chemosensors for a series of aminoalcohols and it was found out that many of them were selective for only one enantiomer of the compound tested, notably changing fluorescence in its presence, while another enantiomer either did not alter the emission or caused opposite changes.