Quantitative Structure-activity Relationship Studies and Nonlinear Optical Properties of 2-Phenylbenzofuran Derivatives: A Density Functional Theory Study

Density functional theory (DFT) calculations were performed in the ground state of 2-phenylbenzofuran using the GGAPBE, PBV86, and meta-GGA TPSS hybrid functionals with the 6-31G(d,p) basis set. First, theoretical calculations were performed using the above functionals to obtain the stable conformer of the molecule. In addition, Mulliken population, natural population, and natural bond orbital analyses were carried out. The molecular electrostatic potential, band gap energies, global and local reactivity descriptors, and nonlinear optical (NLO) properties were studied. Additionally, the NLO properties of 2-phenylbenzofuran and those of its derivatives were investigated by the GGA-PBE/6-31G(d,p) level of theory. The first-order hyperpolarizability of all 2-phenylbenzofuran derivatives was found to be varying from 4.00 × 10-30 to 43.57 × 10-30 (esu), indicating that they possess remarkable NLO properties. In addition, a multiple linear regression model was used to model the relationships between molecular descriptors and the activity of 2-phenylbenzofuran derivatives. Quantitative structure-activity relationship (QSAR) studies were performed using quantum chemical descriptors. The QSAR was applied to determine the relationship between various physico-chemical parameters of the studied compounds and their biological activities. The statistical quality of the QSAR models was assessed using statistical parameters, i.e., R2, R2 adj, and R2 cv.