Synthesis, Spectroscopic (FT-IR, 1H NMR, and UV-Vis) and Nonlinear Optical Properties of a Novel 3-(p-Cyanophenyl)-5-(o, m, p-Iodophenyl)-1-Phenylformazan: Experimental and DFT Studies

Abstract

Three new compounds, 3-(p-cyanophenyl)-5-(o,m,p-iodophenyl)-1-phenylformazans (o, m, p-CNIF), were synthesized. The spectral analyses for o, m, p-CNIF were also carried out by FT-IR, UV-Vis, and NMR spectroscopic techniques. Density Functional Theory (DFT) method with the B3LYP/LanL2DZ level was applied to obtain optimized geometries, vibrational frequencies, and chemical shift values for o, m, p-CNIF. The electronic transitions and spectral features were carried out using the time-dependent DFT (TD-DFT) methodology based on the B3LYP and CAM-B3LYP methods with the LanL2DZ basis set in the gas phase and solvent (methanol). The experimental (FT-IR, UV-Vis, and H-1 NMR) results of o, m, p-CNIF were compared with calculated data obtained by the DFT method. Good correlations were obtained between the predicted FT-IR spectral data and the corresponding experimental ones. TD-DFT/CAM-B3LYP method led to a very good agreement with the experimental absorption spectra in methanol. Besides, chemical reactivity descriptors (ionization potential, chemical hardness, electronegativity, electron affinity, etc.) were calculated by using the DFT/B3LYP/LanL2DZ method. The non-linear optical properties and molecular electrostatic potential of o, m, p-CNIF were surveyed by using the B3LYP/LanL2DZ level.