Department of Applied Chemistry, Shanxi Key Laboratory of Polymer Science & Technology, OME Key Laboratory of Supernomal Material Physics & Chemistry, School of Chemistry and Chemical Engineering, Northwestern Polytechnical University, Xi'an, P. R. China.
Crit Rev Anal Chem. 2021;51(6):565-581. doi: 10.1080/10408347.2020.1753163. Epub 2020 Apr 21.
Photo-sensitive probes based on coumarin deserve extensive attention because of their high biocompatibility, quantum yield, and stability. The synthesis of coumarin and its derivatives is mainly based on four classical methods: Perkin synthesis, Knoevenagel synthesis, Wittig synthesis, and Pechmann synthesis. As everyone knows, fluorescent probes consist of a recognition group, a bridging group, and a luminescent group. Mechanism of fluorescent probes can be roughly summarized into four models: Chelation-induced enhanced fluorescence (CHEF), intramolecular charge transfer (ICT), photoinduced electron transfer (PET), and aggregation-induced luminescence (AIE), which can instruct the design of coumarin-based photo-sensitive probes. Since the fluorescence-based probe was first reported, probes based on coumarin have found widespread application in analytical chemistry, proving to be a selective, efficient, and convenient tool in ion monitoring, molecular monitoring, cell imaging, drug delivery, and many other fields. In this critical review, the synthetic routes of these compounds and the design for fluorescent probes were reported. Furthermore, the recent researches on the employment of coumarin in analytical chemistry were also introduced. Finally, the future research trends and application foreground of coumarin derivatives were forecasted herein.
基于香豆素的光敏感探针因其高生物相容性、量子产率和稳定性而受到广泛关注。香豆素及其衍生物的合成主要基于四种经典方法:Perkin 合成、Knoevenagel 合成、Wittig 合成和 Pechmann 合成。众所周知,荧光探针由识别基团、桥连基团和发光基团组成。荧光探针的机制可以大致概括为四种模型:螯合诱导增强荧光(CHEF)、分子内电荷转移(ICT)、光诱导电子转移(PET)和聚集诱导发光(AIE),这可以指导基于香豆素的光敏感探针的设计。自从首次报道基于荧光的探针以来,基于香豆素的探针已在分析化学中得到广泛应用,成为离子监测、分子监测、细胞成像、药物输送等领域中选择性、高效和方便的工具。在这篇评论中,报告了这些化合物的合成路线和荧光探针的设计。此外,还介绍了香豆素在分析化学中的最新研究进展。最后,本文预测了香豆素衍生物的未来研究趋势和应用前景。