Synthesis and Fluorescence Properties of 2-Phosphoryl Ethyl Ester-3-Indolinone Compounds

目的：合成一系列含吲哚啉酮骨架磷乙酯的类化合物并对其进行荧光性能研究。方法：以不同取代的2-苯基-3H-吲哚-3-酮和亚磷酸二乙酯为起始原料，进行亲核加成反应，优化并合成一系列目标衍生物，并对合成的化合物进行了荧光性能研究。结果与讨论：报道了一种新型合成含吲哚啉酮取代基的磷乙酯类化合物的方法，优化反应条件后以良好至优秀的产率得到了24个化合物。荧光测试结果显示，不同取代基的产物均有良好的荧光效果，值得注意的是，氟取代的化合物荧光效果优于其他取代基，以3da为例，在不同溶剂中的荧光强度有明显的差异，值得进一步探讨和研究。Objective: This paper aims to synthesize a series of compounds containing indolinone skeleton phosphoryl ethyl ester scaffold and systematically investigate their fluorescence properties. Methods: Using differently substituted 2-phenyl-3H-indol-3-one and diethyl phosphite as the starting materials, a nucleophilic addition reaction was carried out to optimize and synthesize a series of target derivatives, and the fluorescence properties of the synthesized compounds were studied. Results and Discussion: A new method for the synthesis of phosphoryl ethyl ester containing indolinone substituents was reported. After optimizing the reaction conditions, 24 compounds were obtained in good to excellent yields. The fluorescence test results show that the products of different substituents have good fluorescence effect. It is worth noting that the fluorescence effect of fluorine-substituted compounds is better than that of other substituents. Taking 3da as an example, the fluorescence intensity in different solvents is obviously different, which is worthy of further discussion and research.