Synthesis and binding ability of mono- and tetrasubstituted aminophosphonate Zn-tetraarylporphyrins towards N- and O-containing organic substrates

摘要

The 1,6-addition of mono- and tetra-amino 5,10,15,20-tetraphenylporphyrins with dimethyl-(3,5-di-tert-butyl-4- oxocyclohexa-2,5-dienylidenemethyl)phosphonate leads to the corresponding mono- and tetrasubstituted aminophosphonate porphyrin derivatives. The binding ability of their Zn(II)-complexes towards 1,4-diazabicyclo[2,2,2]octane, imidazole, 4-(1H-imidazole-1-yl)benzyl alcohol and 4-(1H-imidazole-1-ylmethyl)benzyl alcohol in toluene was investigated by spectrophotometric and 1H NMR titration. It has been determined that the monosubstituted Zntetraarylporphyrin is involved in a two-point selective binding of 4-(1H-imidazole-1-ylmethyl)benzyl alcohol. Taking into account the fact that this binding is accompanied by a clear and easily identifiable response in the UV-vis spectra of the reaction mixture, this metalloporphyrin could be considered as a molecular optical sensing device for selected bidentate N- and O-containing substrates.