Synthesis and molecular recognition of tetraaza[14]annulene complexes containing chiral cavities

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1)Syntheses of pincers-type tetraaza[ 14]annulenes and theirr nickel(II) complexes (3-L, 3-Ni) -The reaction of tetraaza[14]annulenes or their nickel(II) complexes with p-nitrobenzoyl chloride led to the corresponding 7,16-dibenzoylated compounds (1-L, 1-Ni) in refluxing toluene containing triethylamine. The compounds with amino groups (2-L, 2-Ni) were obtained in reduction of the compounds (1-L, 1-Ni). The reaction between the compounds (2-L, 2-Ni) and amino acids gave pincers-type compounds (3-L, 3-Ni).2)Syntheses of strapped tetraaza[14]anulenes and their nickel(II) complexes containing chiral cavities (4-L, 4-Ni) -The reaction of the compounds (3-L, 3-Ni) with 2,6-pyridinedi-carboxylchlorides yielded the corresponding strapped tetraaza[14]anulenes and their nickel(II) complexes containing chiral cavities (4-L, 4-Ni).3)Complexation of pincers-type tetraaza[14]annulenes and their nickel(H) complexes The treatment of the compounds (3-L, 3-Ni) with metal ions (zinc, silver, copper. etc.) offered the corresponding complexes (5-L, 5-Ni).4)Molecular recognition of strapped tetraaza[14]anulenes and their nickel(II) complexes containing chiral cavities The compounds (4-L, 4-Ni) have-the chiral cavities which include some amino acids. The cavities need the amide groups in them because the formation of hydrogen bonds between the compounds (4-L, 4-Ni) and amino acids is very important for the stability of resulting inclusion compounds. The compounds (4-L, 4-Ni) exhibit the difference in the molecular recognition of D-and L-amino acids by ORD spectra.5)Discussion on molecular recognition strapped tetraaza[14]anulenes and their nickel(II) complexes containing chirall cavities The results of IR and NMR spectra show week interaction between the compounds (4-L, 4-Ni) and amino acids with hydrogen bonds.