Synthesis And Spectroscopy Of Imidazole Calix[4]arene Derivatives

Based on calixarene in the lower edge, two novel triaryl imidazole calix[4]arene derivatives modified with arylimidazoles groups were synthesized and their properties of spectrum as host compounds were investigated by UV and fluorescence spectrum to the metal ion as guest. The specific work was described as the follows:Synthesis of triaryl imidazole calix[4]arene derivatives: The intermediate of dibromo butoxycalix[4]arene was prepared under K2CO3 by the reaction of p-tert-butylcalix[4]arene with 1,4-dibromobutane; Substitutive aryl imidazole derivatives containing recognized groups were obtained by one pot reaction. Protected by N2, dibromo butoxycalix[4]arene and substitutive aryl imidazole derivative were carried out in the presence of K2CO3 as the solvent of acetontril and the correspondence aim products, namely 5,11,13,17-four tertiary butyl-26,28-two hydroxy- 25,27-two [2-(4-(N,N-diethyl oxygen acyl methyl amino) phenyl]-4,5-diphenyl imidazole-1] butoxy calix[4]arene(M-1) and 5,11,13,17-four tertiary butyl-26, 28-two hydroxy-25,27-two [2-(4-(N,N-diethyl oxygen acyl methyl amino) phenyl]-benzene and imidazole-1] butoxy calix[4]arene(M-2) were got. Their structures are confirmed by IR、1H NMR、13C NMR, and NMR spectral data which means all of new compounds adopt the cone conformation of calix[4]arene.Spectroscopy of triaryl imidazole calix[4]arene derivatives: Through the ultraviolet spectrum studied, the excitation wavelength of subject M-1 and M-2 are 287 nm and 292 nm, respectively. By fluorescence spectroscopy study, subject M-1 and M-2 can selectively recognize Ag+ and Al3+. In the metal ion interference tests, it is concluded that the existence of Al3+ interfere subject M-1 and M-2 recognize Ag+, the existence of other metal ions is not interfere subject M-1 and M-2 recognize Al3+. The complexing stoichiometric ratio of subject M-1 and M-2 with Ag+ is 1:2, and the complexing stoichiometric ratio of subject M-1 and M-2 with Al3+ is 1:1.So we arrive at the main compound M-1 and M-2 for Al3+ has good recognition; when there is no body compound Al3+, M-1 and M-2 for Ag+ also has a good recognition.