Unusual light-driven amplification through unexpected regioselective photogeneration of five-membered azaheterocyclic AIEgen,Chemical Science

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Unusual light-driven amplification through unexpected regioselective photogeneration of five-membered azaheterocyclic AIEgen
Chemical Science ( IF 7.6 ) Pub Date : 2020-10-19 , DOI: 10.1039/d0sc04725b
Qiyao Li ₁ , Junyi Gong ₁ , Ying Li _{1,

2} , Ruoyao Zhang ₁ , Haoran Wang ₁ , Jianquan Zhang ₁ , He Yan ₁ , Jacky W Y Lam ₁ , Herman H Y Sung ₁ , Ian D Williams ₁ , Ryan T K Kwok ₁ , Min-Hui Li ₃ , Jianguo Wang ₄ , Ben Zhong Tang _{1,

2,

5}

Affiliation

Developing versatile synthetic methodologies with merits of simplicity, efficiency, and environment friendliness for five-membered heterocycles is of incredible importance to pharmaceutical and material science, as well as a huge challenge to synthetic chemistry. Herein, an unexpected regioselective photoreaction to construct a fused five-membered azaheterocycle with an aggregation-induced emission (AIE) characteristic is developed under mild conditions. The formation of the five-membered ring is both thermodynamically and kinetically favored, as justified by theoretical calculation and experimental evidence. Markedly, a light-driven amplification strategy is proposed and applied in selective mitochondria-targeted cancer cell recognition and fluorescent photopattern fabrication with improved resolution. The work not only delivers the first report on efficiently generating a fused five-membered azaheterocyclic AIE luminogen under mild conditions via photoreaction, but also offers deep insight into the essence of the photosynthesis of fused five-membered azaheterocyclic compounds.

中文翻译：

通过五元氮杂环 AIEgen 的意外区域选择性光生成实现不寻常的光驱动放大

开发简单、高效、环境友好的五元杂环通用合成方法对于制药和材料科学具有极其重要的意义，同时也是合成化学面临的巨大挑战。在此，在温和条件下开发了一种意想不到的区域选择性光反应，以构建具有聚集诱导发射（AIE）特性的稠合五元氮杂环。正如理论计算和实验证据所证明的那样，五元环的形成在热力学和动力学上都是有利的。值得注意的是，提出了光驱动放大策略，并将其应用于选择性线粒体靶向癌细胞识别和荧光光图案制造，并提高了分辨率。该工作不仅首次报道了在温和条件下通过光反应高效生成稠合五元氮杂环AIE发光体，而且深入洞察了稠合五元氮杂环化合物光合作用的本质。

更新日期：2020-11-13

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