Synthesis and XRD, FT-IR vibrational, UV–vis, and nonlinear optical exploration of novel tetra substituted imidazole derivatives: A synergistic experimental-computational analysis. (April 2018)

• Record Type: Journal Article
• Authors: Ahmad, Muhammad Saeed; Khalid, Muhammad; Shaheen, Muhammad Ashraf; Tahir, Muhammad Nawaz; Khan, Muhammad Usman; Braga, Ataualpa Albert Carmo; Shad, Hazoor Ahmad
• Is Part Of: Journal of physics and chemistry of solids. Volume 115(2018)
• Page Start: 265
• Page End: 276
• Publication Date: 2018-04
• Subjects: Imidazole derivatives -- Crystal structures -- Spectroscopy -- Frontier molecular orbital -- Non-linear optical properties; Solids -- Periodicals; Solides -- Périodiques; Solids; Periodicals; 530.41
• DOI: 10.1016/j.jpcs.2017.12.054
• Languages: English
• ISSNs: 0022-3697

Abstract

Abstract: Heterocyclic compounds have potential applications in many fields of life. We synthesized novel tetra substituted imidazoles by four-component condensation of benzil, substituted aldehydes, substituted anilines and ammonium acetate as a source of ammonia and acetic acid as the solvent. Their chemical structures were resolved through X-ray crystallographic and spectroscopic (Fourier transform IR and UV–vis) techniques. In addition to experimental analysis, density functional theory (DFT) calculations at the B3LYP/6-311 + G(d, p) level were performed on 4-bromo-2-(1-(4-methoxyphenyl)-4, 5-diphenyl-1 H -imidazole-2-yl)phenol (1 ), 4-bromo-2-(1-(1-naphthalen-yl)-4, 5-diphenyl-1 H -imidazole-2-yl)phenol (2 ), and 2-(1-(2-chlorophenyl)-4, 5-diphenyl-1- H -imidazole-2-yl)-6-methoxyphenol (3 ) to obtain the optimized geometry and spectroscopic (Fourier transform IR and UV–vis) and non-linear optical properties. Frontier molecular orbital analysis was performed at the Hartee-Fock/6-311+g(d, p) and DFT/B3LYP/6-311+G(d, p) levels of theory. Natural bond orbital (NBO) and UV–vis spectral analyses were performed at the M06-2X/6-31+G(d, p) and time-dependent DFT/B3LYP/6-311+G(d, p) levels, respectively. Overall, the DFT findings show good agreement with the experimental data. The hyper conjugative interaction network, which is responsible for the stability of compounds 1, 2 and 3 was explored by the NBO approach. The global reactivity parameters were explored with use of the energy of the frontier molecular orbitals. DFT calculations predict the first-order hyperpolarizabilities of compounds 1, 2 and 3 are 294.89 × 10 −30, 219.45 × 10 −30 and 146.77 × 10 −30 esu, respectively. A two-state model was used to describe the non-linear optical properties of the compounds investigated. Graphical abstract: Image 1 Highlights: Three novel tetrasubstituted imidazole derivatives were synthesized. X-ray diffraction, Fourier transform IR, and UV–vis studies were performed to characterize imidazole derivatives. A computational study was performed as a comparative study. The comparative study revealed good agreement between experimental and density functional theory results. Nonlinear optical properties were determined at the B3LYP/6-311+G(d, p) level. A two-state model is used to describe the nonlinear optical properties.