酰腙类荧光探针的设计合成及其性质研究

Design, Synthesis, and Properties of Acylhydrazone Fluorescent Probes

摘要: 本实验选用3-叔丁基-5-溴水杨醛和马来酸二酰肼作为反应物，以无水乙醇作为溶剂，并添加少量冰醋酸作为催化剂，在60℃条件下通过乙醇回流法成功制备了荧光探针G1。通过1H NMR检测，确认了该探针的纯度较高。进一步的溶剂效应实验表明，与其它溶剂相比，该荧光探针在DMSO (二甲亚砜)中的溶解性最佳。因此，以DMSO为溶剂，以该荧光探针为溶质，进行了后续的性质探究。首先，通过阳离子全扫实验，发现Zn² 、Cu² 和Fe³ 这三种阳离子能够引起荧光探针的特殊响应。接着，分别对这三种阳离子进行了滴定实验、抗干扰实验、含水率测试以及时间响应实验，并得到了相应的工作变化曲线。然后，通过Job图实验确定了荧光探针与这三种阳离子的配位比。最后，通过测定一系列酚类物质的响应情况，发现该荧光探针对于酚类物质具有特殊的识别效果，这表明其可以应用于特定场合中酚类物质的检测。

Abstract: In this experiment, 3-tert butyl-5-bromosalicylic aldehyde and maleic acid dihydrazide were selected as reactants, anhydrous ethanol was used as the solvent, and a small amount of acetic acid was added as the catalyst. The fluorescent probe G1 was successfully prepared by ethanol reflux method at 60˚C. The purity of the probe was confirmed to be high through ¹H NMR detection. Further solvent effect experiments showed that the fluorescence probe had the best solubility in DMSO (dimethyl sulfoxide) compared to other solvents. Therefore, further property investigations were conducted using DMSO as the solvent and the fluorescent probe as the solute. Firstly, through the cation full scan experiment, it was found that Zn² , Cu² , and Fe³ cations can induce a special response of the fluorescent probe. Subsequently, titration experiments, anti-interference experiments, moisture content tests, and time response experiments were conducted on these three cations, and corresponding working change curves were obtained. Then, the coordination ratios of the fluorescent probe to these three cations were determined through Job plot experiments. Finally, by measuring the response of a series of phenolic substances, it was found that the fluorescent probe has a special recognition effect on phenolic substances, indicating that it can be applied to the detection of phenolic substances in specific situations.