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<p>The development of organic photosensitizers (OPSs) for the generation of reactive oxygen species (ROS) is vital across fields such as photodynamic therapy, photocatalysis, and pollutant degradation. Despite significant advancements, existing OPSs face challenges in optimizing the efficiency and selectivity of ROS generation, particularly by controlling their intermolecular packing configurations. This study develops two cationic OPSs, TzBPy and TzSPy, which incorporate the rigid cofacial thiazole [5,4-<i>d</i>]thiazole (Tz) heterocyclic ring and elucidates their noncovalent interactions with cucurbit[8]uril (CB[8]) to form distinct H- and J-type aggregates. It is demonstrated that TzSPy@CB[8] with J-type aggregation exhibits higher ROS production attributed to the enhanced production of hydroxyl radicals (·OH) facilitated by efficient intersystem crossing and suppressed type-II pathway through host-stabilized intermolecular charge transfer. Therefore, TzSPy@CB[8] can exhibit exceptional photocatalytic performance. Notably, it achieves a conversion rate exceeding 99% in the transformation of benzylamine to imine. These findings highlight the unique ability of aggregate science to optimize ROS generation through supramolecular design, offering valuable insights for advancing OPS development and applications in organic synthesis.</p>

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Enhanced efficiency and selectivity in reactive oxygen species generation using thiazolo[5,4-d]thiazole-based supramolecular photosensitizers

  • 期刊论文

  • 发表日期：

    2025年3月21日

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  • Guang Wang,
  • Tongfei Qi,
  • Xianjun Yin,
  • Heng Wu,
  • Duanyang Kong,
  • Bin Liu,
  • Hui-Qing Peng

摘要

The development of organic photosensitizers (OPSs) for the generation of reactive oxygen species (ROS) is vital across fields such as photodynamic therapy, photocatalysis, and pollutant degradation. Despite significant advancements, existing OPSs face challenges in optimizing the efficiency and selectivity of ROS generation, particularly by controlling their intermolecular packing configurations. This study develops two cationic OPSs, TzBPy and TzSPy, which incorporate the rigid cofacial thiazole [5,4-d]thiazole (Tz) heterocyclic ring and elucidates their noncovalent interactions with cucurbit[8]uril (CB[8]) to form distinct H- and J-type aggregates. It is demonstrated that TzSPy@CB[8] with J-type aggregation exhibits higher ROS production attributed to the enhanced production of hydroxyl radicals (·OH) facilitated by efficient intersystem crossing and suppressed type-II pathway through host-stabilized intermolecular charge transfer. Therefore, TzSPy@CB[8] can exhibit exceptional photocatalytic performance. Notably, it achieves a conversion rate exceeding 99% in the transformation of benzylamine to imine. These findings highlight the unique ability of aggregate science to optimize ROS generation through supramolecular design, offering valuable insights for advancing OPS development and applications in organic synthesis.