Development of Rofecoxib-Based Fluorophores from ACQ to AIE by Positional Regioisomerization.

Xinli Wang, Liwei Chen, Renfu Li, Zuoxu Xie, Ming Hu, Shitao Sun, Zhenli Li, Jinle Hao, Bin Lin, Xueyuan Chen, Lijun Xie

ChemPlusChem 2022 Apr

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The development of aggregation-induced emission luminogens (AIEgens) has attracted increasing attention due to their potential applications in various areas in recent years. In this study, a facile conversion from aggregation-caused quenching (ACQ) to aggregation-induced emission (AIE) was achieved by an efficient regioisomerization strategy based on the rofecoxib scaffold. Two compounds, named PYR2 and PYR4, were identified as regioisomers of rofecoxib derivatives to show dramatically different fluorescent properties. Compound PYR2 with an ortho-substituted piperidine group showed typical AIE activity while compound PYR4 with a para-piperidine group exhibited typical ACQ behavior. Notably, compound PYR2 showed polymorphism with two forms of crystals. It was also endowed with reversible mechanochromic luminescence and acidochromic properties. The different fluorescent properties were elucidated by UV/Vis absorption spectroscopy, powder X-ray diffraction, differential scanning calorimetry, and thermogravimetric analyses. Its application as a security ink and in lipid droplets imaging have been demonstrated. © 2022 Wiley-VCH GmbH.

Citation

Xinli Wang, Liwei Chen, Renfu Li, Zuoxu Xie, Ming Hu, Shitao Sun, Zhenli Li, Jinle Hao, Bin Lin, Xueyuan Chen, Lijun Xie. Development of Rofecoxib-Based Fluorophores from ACQ to AIE by Positional Regioisomerization. ChemPlusChem. 2022 Apr;87(4):e202100522