Synthesis, Characterization, and DFT-Based Electronic and Nonlinear Optical Properties of Methyl 1-(arylsulfonyl)-2-aryl-1H-benzo[d]imidazole-6-carboxylates

Abstract

Herein, a series of N -1-sulfonyl substituted derivatives of 2-substituted benzimidazoles ( 2a – 2e ) were designed and synthesized via structural tailoring of the acceptor part of donor−π–acceptor schemes, and their nonlinear optic (NLO) characteristics were reported. The structures of 2a – 2e were investigated and their characterization was accomplished by employing spectroscopic procedures, i.e ., UV–vis, FT-IR, and 1 H and 13 C NMR. Further, a density functional theory (DFT) approach was used to calculate UV–vis, vibrational, and 1 H and 13 C NMR techniques; frontier molecular orbitals (FMOs); global reactivity parameters (GRPs); natural bond orbitals (NBOs); optical and vibrational analysis; and nonlinear optics (NLO). The most promising results were obtained for 6-nitro-2-(4-nitrophenyl)-1-(4-nitrophenylsulfonyl)-1 H -benzo[ d ]imidazole among entitled compounds, as it exhibited the highest ⟨α⟩ and β tot values, showing it is an eye-catching NLO material. This DFT study evokes the interest of researchers regarding the development of benzimidazole-based tempting NLO compounds that could be beneficial in modern hi-tech applications.

A Quantum Chemical Investigation on Structural, Spectroscopic and Nonlinear Optical properties of an Organic Molecule Serotonin

“…Importantly, each compound exhibits a substantial transfer of charge from HOMO to LUMO, along with a reduction in energy level. This observation implies that these substances may serve as promising candidates for a variety of nonlinear optical (NLO) applications [26].…”

Synthesis, characterization and NLO properties of 1,4-phenylenediamine-based Schiff bases: a combined theoretical and experimental approach

“…21 The aim of NLO is to describe the reaction to an applied electric eld. 22,23 Electro-optics for signal processing and frequency variations, 24 particularly in telecommunications, 25 information technology and ber optics, benet greatly from the use of NLO compounds. 21,26 They tend to allow structural alterations to enable a range of NLO behaviors due to their simple chemistry and inexpensive cost of production.…”

Non-linear optical properties of 2,7-naphthyridine derivatives for optical switching applications: a DFT study

“…NLO properties of D–π–A type methyl 1-(arylsulfonyl)-2-aryl-1 H -benzo[ d ]imidazole-6-carboxylates have been investigated using DFT. 26 Liu et al 27 proposed D–π–A type ionic organic materials for second order NLO applications mainly in telecommunications, THz imaging and spectroscopic optical information processing and optical data storage. Vineetha et al 28 developed a series of pyran based bipodal D–π–A chromophores both experimentally and theoretically which are useful for NLO applications.…”