N-(1H-benzo[d]imidazol-2-yl)-1-(3-substituted phenyl)methanimines as optoelectronic and nonlinear optical materials: spectroscopic and computational approach Ojo Nathanael Damilare , Adekusibe Olaide Deborah, Obi-Egbedi Nelson Okpako Department of Chemistry, University of Ibadan, Nigeria Negative environmental impact of fossil fuel and ever-increasing need for renewable energy materials necessitate rigorous search for optoelectronic materials. Photon reabsorption due to small Stokes shift limits the light-emitting potentials of many optical materials. In this research, two benzimidazole Schiff bases(1H-benzo[d]imidazol-2- yl)-1-(3-nitrophenyl)methanimine (BINM) and N-(1H-benzo[d]imidazol-2-yl)-1-(3-hydroxyphenyl)methanimine (BIHM)) were synthesized via one-pot single step condensation and characterized using spectrometric ( 1 H NMR, 13 C NMR, ESI-MS, FTIR) techniques. Optoelectronic and nonlinear optical (NLO) properties of BINM and BIHM were, herein, explored using spectroscopic, density functional theory (DFT) and Monte Carlo (MC) simulation approaches. Electronic absorption, light-harvesting efficiency (LHE) and fluorescence properties were studied in ethanol and dichloromethane experimentally. The LHE, first and second hyperpolarizabilities, and parameters for power conversion efficiency (Open-circuit voltage (V oc ) and injection driving force (ΔG inj )) were computed using time-dependent-DFT/B3LYP/6-311++G(d,p) method. Hyperpolarizabilities were compared with urea (standard NLO material). Binding properties of BINM and BIHM on TiO 2 (anatase 101) were investigated using MC method. Calculated optical properties agree remarkably with experiment. The compounds display large Stokes shift (> 200 nm), appreciable quantum yield and low band gap. This suggests a reduced tendency for photon reabsorption and good optical properties. High LHE (80%) and large hyperpolarizabilities were obtained for BINM. Also, BINM displayed better V oc and ΔG inj than BIHM indicating an improved power conversion efficiency. Negative adsorption energies of BIHM-TiO 2 (-52.7 kJ/mol) and BINM-TiO 2 (-57.3 kJ/mol) interfaces indicate their strong binding interactions on anatase(101). The materials possess potentials for optoelectronic and nonlinear optical 1. N.D. Ojo, R.W. Krause, N.O. Obi-Egbedi, Electronic and nonlinear optical properties of 2-(((5-aminonaphthalen-1-yl) imino)methyl)phenol: Experimental and time-dependent density functional studies, J. Mol. Liq. 319 (2020) 1–8. https://doi. org/10.1016/j.molliq.2020.114157. 2. Z. Tang, L. Ding, The voltage loss in organic solar cells, J. Semicond. 44 (2023) 010202. https://doi.org/10.1088/1674- 4926/44/1/010202. 3. 20%, Sol. Energy. 237 (2022) 96–107. https://doi.org/10.1016/j.solener.2022.03.071.S. V Tatarin, D.E. Smirnov, I. V Taydakov, M.T. Metlin, V. V Emets, S.I. Bezzubov, Tailoring the π-system of benzimidazole ligands towards stable light- harvesting cyclometalated iridium(iii) complexes, Dalt. Trans. 52 (2023) 6435–6450. https://doi.org/10.1039/D3DT00200D. 4. Y.-X. Li, J. Li, H.-B. Zeng, X.-J. Zhang, S. Cosnier, D. Shan, Artificial Light-Harvesting System Based on Zinc Porphyrin and Benzimidazole: Construction, Resonance Energy Transfer, and Amplification Strategy for Electrochemiluminescence, Anal. Chem. 95 (2023) 3493–3498. https://doi.org/10.1021/acs.analchem.2c05559. 5. N.D. Ojo, R.W. Krause, N.O. Obi-Egbedi, Electronic and nonlinear optical properties of 3-(((2-substituted-4-nitrophenyl) imino)methyl)phenol, Comput. Theor. Chem. 1192 (2020) 1–8. https://doi.org/10.1016/j.comptc.2020. 6. 113050.N.O. Obi-Egbedi, N.D. Ojo, Synthesis, Light Harvesting Efficiency, Photophysical and Nonlinear Optical Properties of 3-(5-(4-hydroxybenzylideneamino)naphthalen-1-yliminomethyl)phenol: Spectroscopic and Quantum chemical approach, Res. Chem. Intermed. 47 (2021) 5249–5266. https://doi.org/10.1007/s11164-021-04579-4. 7. V.M. Granchak, T. V. Sakhno, S.Y. Kuchmy, Light-Emitting Materials – Active Components of Luminescent Solar Concentrators, Theor. Exp. Chem. 50 (2014) 1–20. https://doi.org/10.1007/s11237-014-9342-1. 8. G.K. Obiyenwa, S. Banjo, A.K. Oyebamiji, I.A. Olasegun, D.F. Latona, M.D. Adeoye, O.A. Odunola, TD-DFT and DFT Investigation on Electrons Transporting Efficiency of 2-Cyano-2-Pyran-4-Ylidene-Acetic Acid and 2-Cyanoprop-2-Enoic Acid as Acceptors for Thiophene-Based π-Linkers Dye-Sensitized Solar Cells, Eurasian J. Chem. (2023). https://doi. org/10.31489/2959-0663/3-23-9. applications. References
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