Synthesis and Detection Properties of New Linear and Macrocyclic Derivatives of O,O'-Aminobenzylbinols

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 Al³⁺ cations was found in a series of linear derivatives due to a multiple increase in the emission; a fluorescent molecular probe for Hg²⁺ and Al³⁺ cations was also proposed. Among macrocyclic derivatives, the compound with the longest trioxadiamine linker can be used as a molecular probe for Mg²⁺ and Ca²⁺ cations due to the enhancement of fluorescence with a bathofloral shift of the maximum, as well as for Al³⁺ and Hg²⁺ cations due to a strong enhancement of fluorescence without changing the position of the emission maximum.