Journal Article

Iodinated 4(3IP)BC Coumarin Derivative Dipole Moments by a Solvatochromic Shift Method and DFT Approach

Devar, Sulochana, Shivaleela, B, Hanagodimath, S M, Srinath, Katageri, Manjula

2025

Overview

Iodinated coumarin derivative 4(3-Iodo-phenoxymethyl)-benzo[h]-chromen-2-one [4(3IP)BC] molecule, which is biologically active in anticancer and anti-tuberculosis properties, was synthesized to study the photophysical properties and the effect of the molecule in polar and nonpolar solvents at room temperature. Experimentally the dipole moments of the ground state and excited state were estimated by the solvatochromic shift method using three independent Lippert’s, Bakhshiev’s, and Kawaski-Chamma-Viallet’s equations. It was found that as the solvent polarity increases, the bathochromic shift occurs, which is a considerable red shift and the excited state dipole moment was greater than that of the ground state dipole moment. The change of dipole moment was 2.43D by the solvatochromic method and 1.49D by the Reichardt microscopic solvent polarity parameter. The solvent effect on spectral characteristics was studied using the Kamlet and Catalan multiple linear regression method. The interactions of the dielectric of the solvent have more influence than hydrogen bonding operations and polarizability, dipolarity and acidity have more influence than basicity. A theoretical computational study was performed with the Gaussian 16W program using the DFT/B3LYP approach. The HOMO-LUMO energies, ESP maps, Mulliken atomic charges, and nonlinear optical properties of the molecule were studied with optimized geometry. The UV-visible spectra with solvents were estimated using TD-DFT and the change in dipole moments was confirms with experimental value.

• Publisher: CHRIST (Deemed to be University)
• Subject: Solvents