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Updated: May 14, 2026

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Synthesis and Spectroscopic Characterization of Benzimidazole-Derived Schiff Base: Investigation of Optical
Ahmed N Alhakimi1, Sadeq M Al-Hazmy1, Ibrahim A Alhagri1
1Department of Chemistry, College of Science, Qassim University, Buraidah 51452, Saudi Arabia.
Abstract:
This study reports the synthesis and characterization of a novel benzimidazole-derived Schiff base (BIMPB) via the condensation of (1H-benzo[d]imidazol-2-yl)methanamine with 1-phenylbutane-1,3-dione. The structure was confirmed using 1H-NMR, 13C-NMR and FT-IR spectroscopy. Photophysical properties were extensively evaluated, revealing a strong S0 → S2 transition at 212 nm and fluorescence emission peaks at 396 and 410 nm, corresponding to π → π* and n → π* transitions. BIMPB demonstrated significant sensitivity to pH variations, exhibiting blue shifts of 11-23 nm across different environments. Furthermore, the compound acts as a fluorescent chemosensor for Cu2+ and Ca2+ ions, where coordination leads to a substantial reduction in fluorescence intensity accompanied by a distinct blue shift. The interaction between BIMPB and DNA was investigated using UV-Vis and fluorescence titration. The results showed a hypochromic effect and a minor shift in the absorption peak from 342 nm to 340 nm, suggesting a binding mechanism dominated by intercalation or electrostatic interactions. A high binding constant (Kb = 2.1 × 105 M-1) and a fluorescence quenching efficiency of 58.9% confirm the formation of a stable complex. Stern-Volmer analysis indicated a static quenching mechanism. These experimental findings, supported by molecular docking studies (binding energy = -8.3 kcal/mol), highlight the potential of BIMPB as a sensitive molecular probe for DNA-targeting and chemical sensing applications.
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