Synthesis, Spectroscopic (FT-IR, H-1 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

TOY M., VURAL H., ŞENÖZ H.

POLYCYCLIC AROMATIC COMPOUNDS, vol.43, no.8, pp.7279-7296, 2023 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 43 Issue: 8
  • Publication Date: 2023
  • Doi Number: 10.1080/10406638.2022.2133903
  • Journal Name: POLYCYCLIC AROMATIC COMPOUNDS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Aerospace Database, Applied Science & Technology Source, CAB Abstracts, Chemical Abstracts Core, Communication Abstracts, Food Science & Technology Abstracts, Metadex, Pollution Abstracts, Veterinary Science Database, Civil Engineering Abstracts
  • Page Numbers: pp.7279-7296
  • Keywords: Formazan, spectral analysis, DFT, nonlinear optics, SPECTRAL PROPERTIES, CRYSTAL-STRUCTURE, MOLECULAR DOCKING, NMR, NLO
  • Hacettepe University Affiliated: Yes

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.