Issue 2, 2021

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

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.

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

Supplementary files

Article information

Article type
Edge Article
Submitted
27 avq 2020
Accepted
17 okt 2020
First published
19 okt 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2021,12, 709-717

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

Q. Li, J. Gong, Y. Li, R. Zhang, H. Wang, J. Zhang, H. Yan, J. W. Y. Lam, H. H. Y. Sung, I. D. Williams, R. T. K. Kwok, M. Li, J. Wang and B. Z. Tang, Chem. Sci., 2021, 12, 709 DOI: 10.1039/D0SC04725B

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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