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

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Abstract

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. This journal is

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Li, Q., Gong, J., Li, Y., Zhang, R., Wang, H., Zhang, J., … Tang, B. Z. (2021). Unusual light-driven amplification through unexpected regioselective photogeneration of five-membered azaheterocyclic AIEgen. Chemical Science, 12(2), 709–717. https://doi.org/10.1039/d0sc04725b

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