Synthesis and chiral recognition of nickel(II) macrocyclic complex with (R)-naphthylethyleneamine pendant groups and its self-assembled framework

A novel nickel(II) hexaaza macrocyclic complex, [Ni(L^R,R)] (ClO₄)₂ (), containing chiral pendant groups was synthesized by an efficient one-pot template condensation and characterized (L^R,R1,8-di((R)-α-methylnaphthyl)-1,3,6,8,10,13- hexaazacyclotetradecane). The crystal structure of compound was determined by single-crystal X-ray analysis. The complex was found to have a square-planar coordination environment for the nickel(II) ion. Open framework [Ni(L ^R,R)]₃[C₆H₃(COO)₃] ₂ () was constructed from the self-assembly of compound with deprotonated 1,3,5-benzenetricarboxylic acid, BTC^3-. Chiral discrimination of rac-1,1'-bi-2-naphthol and rac-2,2,2-trifluoro-1-(9-anthryl) ethanol was performed to determine the chiral recognition ability of the chiral complex () and its self-assembled framework (). Binaphthol showed a good chiral discrimination on the framework (). The optimum experimental conditions for the chiral discrimination were examined by changing the weight ratio between the macrocyclic complex or self-assembled framework and racemates. The detailed synthetic procedures, spectroscopic data including single-crystal X-ray analysis, and the results of the chiral recognition for the compounds are described.