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<p>This study investigates the singlet oxygen O₂(¹Δ<sub>g</sub>) generation capabilities and photophysical properties of eight synthesized alkoxy- and aryloxy-substituted BODIPY derivatives across eight different solvents. The production of O₂(¹Δ<sub>g</sub>) was confirmed by monitoring its characteristic near-infrared (NIR) phosphorescence and through chemical trapping experiments using 1,3-diphenylisobenzofuran. Among the series, phenanthrenyloxy-BODIPY demonstrated outstanding performance, achieving a singlet oxygen quantum yield (Φ<sub>Δ</sub>) of up to 0.85. Photophysical analysis indicated that this high efficiency originates from a photoinduced electron transfer (PET) process within the molecule. All synthesized compounds exhibit significantly enhanced O₂(¹Δ<sub>g</sub>) generation over the unsubstituted BODIPY reference (Φ<sub>Δ</sub> ≈ 0.10). The Φ<sub>Δ</sub> was found to be modulated by solvent polarity, while the carbon chain length of the alkoxy substituents has only a marginal influence. Density functional theory calculations, which reveals the spatial distribution of the highest occupied and lowest unoccupied molecular orbitals (HOMO/LUMO), provides further evidence for the proposed PET mechanism in phenanthrenyloxy-BODIPY. The established structure-property relationships offer valuable insights for designing efficient, heavy-atom-free BODIPY photosensitizers, with promising applications in photodynamic therapy for cancer.</p>

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Toward Efficient Halogen- and Heavy Metal-Free Photosensitizers: Alkoxy/Aryloxy-BODIPYs for Effective Singlet Oxygen Generation

  • 期刊论文

  • 发表日期：

    2026年6月23日

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  • Wenbin Hu,
  • Yuheng Wei,
  • Huimin Wang,
  • Xian-Fu Zhang,
  • Mingye Fan

摘要

This study investigates the singlet oxygen O₂(¹Δg) generation capabilities and photophysical properties of eight synthesized alkoxy- and aryloxy-substituted BODIPY derivatives across eight different solvents. The production of O₂(¹Δg) was confirmed by monitoring its characteristic near-infrared (NIR) phosphorescence and through chemical trapping experiments using 1,3-diphenylisobenzofuran. Among the series, phenanthrenyloxy-BODIPY demonstrated outstanding performance, achieving a singlet oxygen quantum yield (ΦΔ) of up to 0.85. Photophysical analysis indicated that this high efficiency originates from a photoinduced electron transfer (PET) process within the molecule. All synthesized compounds exhibit significantly enhanced O₂(¹Δg) generation over the unsubstituted BODIPY reference (ΦΔ ≈ 0.10). The ΦΔ was found to be modulated by solvent polarity, while the carbon chain length of the alkoxy substituents has only a marginal influence. Density functional theory calculations, which reveals the spatial distribution of the highest occupied and lowest unoccupied molecular orbitals (HOMO/LUMO), provides further evidence for the proposed PET mechanism in phenanthrenyloxy-BODIPY. The established structure-property relationships offer valuable insights for designing efficient, heavy-atom-free BODIPY photosensitizers, with promising applications in photodynamic therapy for cancer.