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<p>In this study, we designed and synthesized a novel phenanthro-imidazole derivative (Ph-IMI, <b>a</b>) and its tetracoordinated boron complexes Ph-IMI-BF<sub>2</sub> (<b>b</b>) and Ph-IMI-BPh<sub>2</sub> (<b>c</b>) in good yields (96%, 72%, and 68%, respectively). All compounds were characterized experimentally (1&#xa0;H NMR, FTIR, UV–Vis, fluorescence, TGA) and theoretically (DFT/TD-DFT at B3LYP-D3/6-311 + G(d, p) level). Boron complexation dramatically enhanced thermal stability: T5% increased from 74&#xa0;°C (<b>a</b>) to 147&#xa0;°C (<b>b</b>) and 328&#xa0;°C (<b>c</b>). Optically, BF₂ coordination produced a green emission with a large Stokes shift (11700&#xa0;cm⁻¹) and a reduced HOMO–LUMO gap (3.30&#xa0;eV vs. 3.72&#xa0;eV for <b>a</b>), while BPh<sub>2</sub> coordination afforded an unusual white emission (two bands at 464 and 571&#xa0;nm) with a Stokes shift of 9161&#xa0;cm⁻¹ and a gap of 3.31&#xa0;eV. Frontier molecular orbital analysis revealed pronounced intramolecular charge transfer, consistent with the observed bathochromic shifts. Preliminary docking against p38α MAP kinase (PDB:1A9U) showed that boron complexation progressively improves binding affinity, with <b>c</b> exhibiting the strongest predicted binding energy (-10.0&#xa0;kcal/mol) due to additional π-π stacking and polar interactions. These findings demonstrate that coordination with BF<sub>2</sub> and especially BPh<sub>2</sub> enables systematic tuning of thermal stability, fluorescence color (blue → green → white), and receptor binding, establishing boron-phenanthro-imidazole complexes as promising scaffolds for optoelectronic and bioimaging applications.</p> Graphical Abstract <p></p>

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Design and DFT Study of π-Rich Boron Complexes of Tetraphenyl Imidazole: Correlation between Photophysical Properties and Binding Affinity toward p38α MAP Kinase

  • 期刊论文

  • 发表日期：

    2026年6月16日

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  • Soumaya Agren,
  • Marwa Chaabene,
  • Chaima Hassouna,
  • Jamal El Haskouri,
  • Mohamed Lahcini,
  • Mohamed Hassen V. Baouab

摘要

In this study, we designed and synthesized a novel phenanthro-imidazole derivative (Ph-IMI, a) and its tetracoordinated boron complexes Ph-IMI-BF2 (b) and Ph-IMI-BPh2 (c) in good yields (96%, 72%, and 68%, respectively). All compounds were characterized experimentally (1 H NMR, FTIR, UV–Vis, fluorescence, TGA) and theoretically (DFT/TD-DFT at B3LYP-D3/6-311 + G(d, p) level). Boron complexation dramatically enhanced thermal stability: T5% increased from 74 °C (a) to 147 °C (b) and 328 °C (c). Optically, BF₂ coordination produced a green emission with a large Stokes shift (11700 cm⁻¹) and a reduced HOMO–LUMO gap (3.30 eV vs. 3.72 eV for a), while BPh2 coordination afforded an unusual white emission (two bands at 464 and 571 nm) with a Stokes shift of 9161 cm⁻¹ and a gap of 3.31 eV. Frontier molecular orbital analysis revealed pronounced intramolecular charge transfer, consistent with the observed bathochromic shifts. Preliminary docking against p38α MAP kinase (PDB:1A9U) showed that boron complexation progressively improves binding affinity, with c exhibiting the strongest predicted binding energy (-10.0 kcal/mol) due to additional π-π stacking and polar interactions. These findings demonstrate that coordination with BF2 and especially BPh2 enables systematic tuning of thermal stability, fluorescence color (blue → green → white), and receptor binding, establishing boron-phenanthro-imidazole complexes as promising scaffolds for optoelectronic and bioimaging applications.

Graphical Abstract