Multidisciplinary Computational Study of 1-(4-Chlorophenyl)-3-(4-fluorophenyl)triazene: DFT, NLO Properties, Hirshfeld Surface Analysis, and Molecular Docking

Abstract

In the present study, the structural, electronic, NLO, intermolecular, and biological activities of the compound 1-(4-chlorophenyl)-3-(4-fluorophenyl) triazene (I) were studied in detail by the application of multiple computational methods. The optimized structure of the compound was computed at the B3LYP/6-311++G(d,p) level in the context of DFT. The accuracy of the approach was confirmed by the high degree of conformity of the obtained data with experimental crystallographic data. The presence of π-conjugation and planar structure in the compound is due to the presence of the triazene group. The delocalization of electrons in the compound is effective. The energy gap was computed to be 3.786 eV by considering the boundary molecular orbitals. The compound was found to be stable and reactive to some extent. The molecular electrostatic potential surface was computed and showed conformity with the compound’s behavior. The high values of the compound’s dipole moment, average polarizability, and first-order hyperpolarizability indicate the compound’s possible strong nonlinear optical (NLO) activities. Global reactivity descriptors have indicated that the polarity of the solvent affects the electronic structure and the dipole moment and softness values. In the comparison of the Mulliken and NPA methods, the NPA method was found to be more reliable in the context of conjugated systems. The thermodynamic values obtained in the range of 100-1000 K indicated that the compound is thermally stable. The Hirshfeld surface analysis (HSA) indicated that H···H, Cl···H/H···Cl, and C···H/H···C interactions were the most important interactions. The results indicated that weak hydrogen bonding and van der Waals interactions played an important role in the stability of the crystal. The molecular docking analysis indicated that the compound has a high affinity for the HER2 receptor with a binding energy of –9.6 kcal mol-1. The results indicated that the compound has the potential to be used in the development of NLO materials and drugs.

Keywords

• Triazene derivatives
• DFT
• NLO properties
• Hirshfeld surface analysis
• Molecular docking
• HER2 receptor

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