具有显着不同 AIE 特性的天然香豆素异构体：机理和应用,ACS Central Science

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具有显着不同 AIE 特性的天然香豆素异构体：机理和应用
ACS Central Science ( IF 12.7 ) Pub Date : 2023-04-19 , DOI: 10.1021/acscentsci.3c00012
Shan-Shan Chen _{1,

2,

3} , Haoran Wang _{4,

5} , Bo Wu ₄ , Qiyao Li ₄ , Junyi Gong ₄ , Yun-Li Zhao ₂ , Yun Zhao _{1,

3} , Xia Xiao ₂ , Jacky W Y Lam ₅ , Zheng Zhao ₄ , Xiao-Dong Luo _{1,

2} , Ben Zhong Tang _{4,

5}

Affiliation

聚集诱导发光体（AIEgens）在光电子学和生物医学领域具有重要意义。然而，流行的将转子与传统荧光团相结合的设计理念限制了AIEgens的想象力和结构多样性。灵感来自药用植物Toddalia asiatica的荧光根, 我们发现了两种非常规的无转子 AIEgens, 5-methoxyseselin (5-MOS) 和 6-methoxyseselin (6-MOS)。有趣的是，香豆素异构体的轻微结构差异导致在水性介质中聚集时完全相反的荧光特性。进一步的机理研究表明，5-MOS 在质子溶剂的帮助下形成不同程度的聚集体，导致电子/能量转移，这是其独特的 AIE 特征的原因，即在水介质中发射减少但在晶体中发射增强。同时，对于6-MOS，分子内运动（RIM）机制的常规限制是其AIE特征的原因。更有趣的是，5-MOS 独特的水敏荧光特性使其成功应用于免洗线粒体成像。

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Natural Coumarin Isomers with Dramatically Different AIE Properties: Mechanism and Application

Aggregation-induced emission luminogens (AIEgens) are of great importance in optoelectronics and biomedical fields. However, the popular design philosophy by combining rotors with traditional fluorophores limits the imagination and structural diversity of AIEgens. Inspired by the fluorescent roots of the medicinal plant Toddalia asiatica, we discovered two unconventional rotor-free AIEgens, 5-methoxyseselin (5-MOS) and 6-methoxyseselin (6-MOS). Interestingly, a slight structural difference of the coumarin isomers leads to completely contrary fluorescent properties upon aggregation in aqueous media. Further mechanism investigation indicates that 5-MOS forms different extents of aggregates with the assistance of protonic solvents, leading to electron/energy transfer, which is responsible for its unique AIE feature, i.e., reduced emission in aqueous media but enhanced emission in crystal. Meanwhile, for 6-MOS, the conventional restriction of the intramolecular motion (RIM) mechanism is responsible for its AIE feature. More interestingly, the unique water-sensitive fluorescence property of 5-MOS enables its successful application for wash-free mitochondria imaging. This work not only demonstrates an ingenious tactic to seek new AIEgens from natural fluorescent species but also benefits the structure design and application exploration of next-generation AIEgens.

更新日期：2023-04-19

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