Synthesis and Chiral Recognition of Nickel(II) Macrocyclic Complex with (R)‐Naphthylethyleneamine Pendant Groups and its Self‐Assembled Framework |
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Authors: | Kil Sik Min Mi Jung Park Jae Jeong Ryoo |
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Institution: | Department of Chemistry Education, Kyungpook National University, , Daegu, 702‐701 Republic of Korea |
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Abstract: | A novel nickel(II) hexaaza macrocyclic complex, Ni(LR,R)](ClO4)2 ( 1 ), containing chiral pendant groups was synthesized by an efficient one‐pot template condensation and characterized (LR,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(LR,R)]3C6H3(COO)3]2 ( 2 ) was constructed from the self‐assembly of compound 1 with deprotonated 1,3,5‐benzenetricarboxylic acid, BTC3?. 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. Chirality, 25:54‐58, 2013 © 2012 Wiley Periodicals, Inc. |
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Keywords: | naphthylethylamine chiral compound nickel(II) ion binaphthol chiral recognition macrocyclic ligand |
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