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

Shumaila Aslam; Muhammad Haroon; Tashfeen Akhtar; Muhammad Arshad; Muhammad Khalid; Zahid Shafiq; Muhammad Imran; Aman Ullah

doi:10.1021/acsomega.2c02805

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

ACS Omega. 2022 Aug 23;7(35):31036-31046. doi: 10.1021/acsomega.2c02805. eCollection 2022 Sep 6.

Authors

Shumaila Aslam¹, Muhammad Haroon^{1

2}, Tashfeen Akhtar¹, Muhammad Arshad³, Muhammad Khalid^{4

5}, Zahid Shafiq⁶, Muhammad Imran⁷, Aman Ullah⁸

Affiliations

¹ Department of Chemistry, Mirpur University of Science and Technology (MUST), 10250 Mirpur, Azad Jammu and Kashmir, Pakistan.
² Department of Chemistry, Government Major Muhammad Afzal Khan (Shaheed), Boys Degree College Afzalpur, Mirpur (Affiliated with Mirpur University of Science and Technology (MUST)), 10250 Mirpur, Azad Jammu and Kashmir, Pakistan.
³ Department of Chemical Engineering, College of Engineering, King Khalid University, Abha 62529, Saudi Arabia.
⁴ Institute of Chemistry, Khwaja Fareed University of Engineering and Information Technology, Rahim Yar Khan 64200, Pakistan.
⁵ Centre for Theoretical and Computational Research, Khwaja Fareed University of Engineering and Information Technology, Rahim Yar Khan 64200, Pakistan.
⁶ Institute of Chemical Sciences, Bahauddin Zakariya University, Multan 60800, Pakistan.
⁷ Department of Chemistry, Faculty of Science, King Khalid University, Abha 61413, P.O. Box 9004, Saudi Arabia.
⁸ Department of Agricultural, Food and Nutritional Science, Faculty of Agricultural, Life and Environmental Sciences, University of Alberta, Edmonton, Alberta T6G 2R3, Canada.

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 ¹H and ¹³C NMR. Further, a density functional theory (DFT) approach was used to calculate UV-vis, vibrational, and ¹H and ¹³C 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)-1H-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.