Synthesis, FT-IR, NMR and DFT analysis of a new salophen based on diaminophenazine moiety

Abstract

As a rigid diamine, diaminophenazine was prepared by the condensation of 1,2-phenylene diamine and characterized by FT-IR and EI mass spectroscopy. Then, a new salophen was synthesized based on a phenazine moiety, by the condensation of salicylaldehyde and synthesized diamine. The prepared salophen was characterized by FT-IR and 1H NMR spectroscopy. The geometry of the prepared salophen was examined by density functional theory (DFT) method at B3LYP/6-31G(d) level. Also, due to the structure of salophen, IR and NMR spectra of the more stable isomers were calculated by DFT method using camB3LYP/6-311+G(d) level and compared with the experimental results. Also, root mean square (RMS) errors observed between the experimental and calculated results for the NMR and IR were 0.75ppm and 94.9cm−1.