Synthesis and chiral recognition of nickel(II) macrocyclic complex with (R)-naphthylethyleneamine pendant groups and...

A novel nickel(II) hexaaza macrocyclic complex, [Ni(L(R,R))](ClO(4))(2) (1), containing chiral pendant groups was synthesized by an efficient one-pot template condensation and characterized (L(R,R) ═1,8-di((R)-α-methylnaphthyl)-1,3,6,8,10,13-hexaazacyclotetradecane). The crystal structure of compound 1 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) [C(6)H(3)(COO)(3)](2) (2) was constructed from the self-assembly of compound 1 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 (1) and its self-assembled framework (2). Binaphthol showed a good chiral discrimination on the framework (2). The optimum experimental conditions for the chiral discrimination were examined by changing the weight ratio between the macrocyclic complex 1 or self-assembled framework 2 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.