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 ¹H 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.

Keywords:

• Formazan
• spectral analysis
• DFT
• nonlinear optics

Acknowledgment

The authors thank the Amasya University Scientific Research Projects Unit for their financial support.

Disclosure statement

No potential conflict of interest was reported by the author(s).

Additional information

Funding

This work was supported by Amasya University Research Fun with the project number FMB-BAP 17-0275.