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<p>A novel benzimidazole derivative, 1-(4-chlorobenzyl)-2-(4-chlorophenyl)-4-fluoro-1H-benzo[d]imidazole (CCHFB), was synthesized via a three-component condensation reaction involving 3-fluorobenzene-1,2-diamine, 5-chloro-2-hydroxybenzaldehyde, and ammonium acetate in the presence of ZnO nanoparticles as a catalyst. The synthesized compound was further functionalized with SiO<sub>2</sub> nanoparticles to investigate enhancements in physicochemical and biological properties. Comprehensive spectral analyses including UV–Vis, fluorescence, NMR, and FT-IR confirmed successful functionalization and highlighted the molecular interactions between CCHFB and the nanoparticle surface. UV–Vis spectra showed enhanced absorbance, while fluorescence quenching indicated possible electron transfer interactions. FT-IR analysis revealed shifts in azomethine group vibrations, confirming nanoparticle binding. Biological evaluations demonstrated that functionalized CCHFB exhibited notable antioxidant activity (via phosphomolybdenum and DPPH assays), significant α-amylase inhibitory potential, and enhanced antibacterial effects against both Gram-positive and Gram-negative strains, compared to unmodified CCHFB. Stability studies revealed that the functionalized compound retained over 92% structural integrity over 24&#xa0;h in physiological buffer. These findings suggest that SiO₂-functionalized CCHFB is a promising candidate for pharmaceutical and biomedical applications due to its enhanced stability, bioactivity, and broad-spectrum antimicrobial properties.</p> Graphical Abstract <p></p>

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Functionalization of Halo-Hydroxy Benzimidazole onto SiO2 Nanoparticles: Catalytic, Photophysical, and Biological Investigations for Sustainable Applications

  • 期刊论文

  • 发表日期：

    2025年10月30日

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  • Xiaojian Liu,
  • Yanqi Zhou,
  • Kanagaraj Rajalakshmi,
  • K. Jayamoorthy,
  • B. Subash,
  • Selvaraj Muthusamy,
  • Dongwei Zhu,
  • Yanping Zhao

摘要

A novel benzimidazole derivative, 1-(4-chlorobenzyl)-2-(4-chlorophenyl)-4-fluoro-1H-benzo[d]imidazole (CCHFB), was synthesized via a three-component condensation reaction involving 3-fluorobenzene-1,2-diamine, 5-chloro-2-hydroxybenzaldehyde, and ammonium acetate in the presence of ZnO nanoparticles as a catalyst. The synthesized compound was further functionalized with SiO2 nanoparticles to investigate enhancements in physicochemical and biological properties. Comprehensive spectral analyses including UV–Vis, fluorescence, NMR, and FT-IR confirmed successful functionalization and highlighted the molecular interactions between CCHFB and the nanoparticle surface. UV–Vis spectra showed enhanced absorbance, while fluorescence quenching indicated possible electron transfer interactions. FT-IR analysis revealed shifts in azomethine group vibrations, confirming nanoparticle binding. Biological evaluations demonstrated that functionalized CCHFB exhibited notable antioxidant activity (via phosphomolybdenum and DPPH assays), significant α-amylase inhibitory potential, and enhanced antibacterial effects against both Gram-positive and Gram-negative strains, compared to unmodified CCHFB. Stability studies revealed that the functionalized compound retained over 92% structural integrity over 24 h in physiological buffer. These findings suggest that SiO₂-functionalized CCHFB is a promising candidate for pharmaceutical and biomedical applications due to its enhanced stability, bioactivity, and broad-spectrum antimicrobial properties.

Graphical Abstract