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<p>A novel Schiff base derivative, <i>(E)-N′-(2,6-dimethoxybenzylidene)-3-hydroxy-2-naphthohydrazide</i> (F5), was synthesized and systematically investigated for its structural, electronic, and nonlinear optical (NLO) properties. The compound was characterized by FTIR and NMR spectroscopy, while single-crystal X-ray diffraction confirmed its orthorhombic <i>Pbca</i> crystal system stabilized by C–H···O and C–H···<i>π</i> interactions. Hirshfeld surface analysis revealed dominant H···H (44.5%), C···H (24.5%), O···H (17.2%), and N···H (2.8%) contributions. The optical band gap was estimated to be 5.23&#xa0;eV from UV–Vis analysis, while DFT calculations yielded a HOMO–LUMO energy gap of 2.782&#xa0;eV, indicating good electronic stability. Molecular electrostatic potential (MEP) and RDG–QTAIM analyses confirmed distinct nucleophilic and electrophilic regions and the presence of significant non-covalent interactions. Third-order NLO properties evaluated via Z-scan showed a high nonlinear susceptibility (<i>χ</i><sup>(3)</sup> = 3.85 × 10<sup>−8</sup> esu) and an optical limiting threshold of 1&#xa0;kW&#xa0;cm<sup>−2</sup>. These enhanced NLO responses are attributed to a donor–π–acceptor (D–π–A) framework, where electron-donating methoxy groups and the electron-withdrawing carbonyl moiety facilitate intramolecular charge transfer (ICT) across a nearly planar conjugated system. Additionally, molecular docking studies are used to compare the titled compound <b>(F5)</b> with a co-crystal ligand. The binding energy of the <b>F5</b>-complex is found to be − 7.339&#xa0;kcal/mol. These combined features establish <Emphasis Type="BoldItalic">(E)-N′-(2,6-dimethoxybenzylidene)-3-hydroxy-2-naphthohydrazide</Emphasis> as a promising multifunctional material for advanced optoelectronic and photonic applications.</p>

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Synthesis, structural elucidation, hirshfeld surface analysis, DFT studies, and nonlinear optical exploration of a schiff base derivative: an experimental and computational approach

  • 期刊论文

  • 发表日期：

    2026年5月13日

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  • V. Karthik,
  • Anand Sekar,
  • S. Neetha,
  • T. N. Lohith,
  • Rajiv Patel,
  • Neelamma B. Gummagol,
  • M. A. Sridhar

摘要

A novel Schiff base derivative, (E)-N′-(2,6-dimethoxybenzylidene)-3-hydroxy-2-naphthohydrazide (F5), was synthesized and systematically investigated for its structural, electronic, and nonlinear optical (NLO) properties. The compound was characterized by FTIR and NMR spectroscopy, while single-crystal X-ray diffraction confirmed its orthorhombic Pbca crystal system stabilized by C–H···O and C–H···π interactions. Hirshfeld surface analysis revealed dominant H···H (44.5%), C···H (24.5%), O···H (17.2%), and N···H (2.8%) contributions. The optical band gap was estimated to be 5.23 eV from UV–Vis analysis, while DFT calculations yielded a HOMO–LUMO energy gap of 2.782 eV, indicating good electronic stability. Molecular electrostatic potential (MEP) and RDG–QTAIM analyses confirmed distinct nucleophilic and electrophilic regions and the presence of significant non-covalent interactions. Third-order NLO properties evaluated via Z-scan showed a high nonlinear susceptibility (χ(3) = 3.85 × 10−8 esu) and an optical limiting threshold of 1 kW cm−2. These enhanced NLO responses are attributed to a donor–π–acceptor (D–π–A) framework, where electron-donating methoxy groups and the electron-withdrawing carbonyl moiety facilitate intramolecular charge transfer (ICT) across a nearly planar conjugated system. Additionally, molecular docking studies are used to compare the titled compound (F5) with a co-crystal ligand. The binding energy of the F5-complex is found to be − 7.339 kcal/mol. These combined features establish (E)-N′-(2,6-dimethoxybenzylidene)-3-hydroxy-2-naphthohydrazide as a promising multifunctional material for advanced optoelectronic and photonic applications.