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

Qiyao Li; Junyi Gong; Ying Li; Ruoyao Zhang; Haoran Wang; Jianquan Zhang; He Yan; Jacky W. Y. Lam; Herman H. Y. Sung; Ian D. Williams; Ryan T. K. Kwok; Min-Hui Li; Jianguo Wang; Ben Zhong Tang

doi:10.1039/D0SC04725B

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

Qiyao Li,‡^a Junyi Gong,

‡^a Ying Li,^ac Ruoyao Zhang,^a Haoran Wang,^a Jianquan Zhang,^a He Yan,

^a Jacky W. Y. Lam,^a Herman H. Y. Sung,^a Ian D. Williams,

^a Ryan T. K. Kwok,^a Min-Hui Li,

^d Jianguo Wang

*^b and Ben Zhong Tang

*^ace

Author affiliations

* Corresponding authors

^a Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction, State Key Laboratory of Molecular Nanoscience, Division of Life Science, Department of Chemical and Biomedical Engineering and Institute for Advanced Study, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
E-mail: tangbenz@ust.hk

^b College of Chemistry and Chemical Engineering, Inner Mongolia Key Laboratory of Fine Organic Synthesis, Inner Mongolia University, Hohhot 010021, China

^c Center for AIE Research, College of Materials Science and Engineering, Shenzhen University, Shenzhen 518060, China

^d Chimie ParisTech, PSL University Paris, CNRS, Institut de Recherche de Chimie Paris, Paris 75005, France

^e Center for Aggregation-induced Emission, SCUT–HKUST Joint Research Institute, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510640, China

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 article is part of the themed collection: Most popular 2021 physical and theoretical chemistry articles, 2021

Chemical Science

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

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