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1,4-Benzodioxane Substituted Aza-BODIPY: Towards Photostable yet Efficient Triplet Photosensitizer. | LitMetric

AI Article Synopsis

  • Researchers synthesized a new type of aza-BODIPY with special substituents that enhance its light-absorbing properties and allow it to maintain a long-lived excited state.
  • The compound produced strong singlet oxygen formation in tests and absorbed light in the therapeutic range (678 nm), making it potentially effective for medical applications.
  • It demonstrated excellent stability under light and heat, indicating its viability for future uses in photocatalysis and photodynamic therapy.

Article Abstract

We report herein the synthesis of aza-BODIPY substituted with 1,4-benzodioxane-6-yl substituents at 3,5 positions of the chromophore system. Both pyrrole rings of the aza-BODIPY in question were substituted with bromine atoms in order to induce highly desirable photophysical properties, such as highly populated excited triplet state (T) and long excited triplet-state lifetime (τ) of 21 μs. The photosensitized oxygenation of a model compounds, viz. DPBF, points to a high singlet oxygen and/or other ROS formation quantum yield of 0.42. The photosensitizer studied exhibited an absorption band within the so-called "therapeutic window", with λ 678 nm. As estimated by CV/DPV measurements the 1,4-benzodioxane-6-yl substituted aza-BODIPYs studied exhibited a multi-electron oxidations at a relatively low potentials (E), pointing to the very good electron-donating properties of these molecules. High photostability and thermal stability was observed for all compounds studied. The good singlet oxygen quantum yield measured combined with an exceptional photostability makes this aza-BODIPY a promising candidate for applications such as photocatalysis and photodynamic therapy (PDT).

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Source
http://dx.doi.org/10.1002/asia.202400885DOI Listing

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