8-羟基喹啉衍生物的合成及其荧光性质

发布时间：2018-04-21 03:00

本文选题：8-羟基喹啉 + 荧光探针　；参考：《东华大学》2017年硕士论文

【摘要】：本论文通过在2-苯乙烯基-8-羟基喹啉衍生物中乙烯基苯上引入不同的取代基,探索引入吸电子基团与供电子基团调控荧光性质的规律。并初步研究了2-苯乙烯基-8-羟基喹啉类化合物作为探针应用于金属离子检测。本论文分为五章:第一章,简述了金属锌在人体生长发育的作用,8-羟基喹啉类化合物的应用优点。然后阐述了荧光的产生,以及影响荧光的因素,荧光探针的发光机理。描述了8-羟基喹啉类衍生物的应用领域与研究进展。提出论文的设计思路与研究内容。第二章,实验部分。通过两步反应制备得到六个2-苯乙烯基-8-羟基喹啉衍生物,并对其进行了核磁氢谱、核磁碳谱以及质谱的结构表征。第三章,对所制备的六个2-苯乙烯基-8-羟基喹啉衍生物分别与Zn2+和Cd2+的配合物进行荧光光谱和紫外-可见光光谱的测试,测试条件包括:水含量、反应时间、金属离子浓度等。通过对比这些化合物的荧光最大发射波长,研究吸电子取代基和供电子取代基对化合物的荧光性质所产生的影响。结果显示引入吸电子基团时,荧光的最大发射波长有红移趋势;反之,引入供电子基团可观察到荧光的最大发射波长有蓝移的趋势。对六个2-苯乙烯基-8-羟基喹啉衍生物进行了荧光光谱和紫外-可见光光谱的测试,并与其金属离子配合物进行比较,结果显示电子效应的影响一致。第四章,选择2-(4-甲基苯乙烯基)-8-羟基喹啉作为探针进行细胞成像实验。荧光显微镜的结果表明细胞中加入探针后,暗场图中仅仅观察到十分微弱的绿色荧光。而在细胞中加进一步引入金属锌离子后,可以观察到明显的黄色荧光。第五章,全文总结。本文结果表明溶剂(外部环境),取代基(分子结构)都对分子的电子云密度产生影响。探针与金属锌离子、镉离子进行配位,不但体系的电子云密度发生改变,同时分子平面的刚性变强,两者共同导致配合物的荧光光谱发生规律性变化。
[Abstract]:In this paper, different substituents of vinylbenzene were introduced into 2-styrene-8-hydroxyquinoline derivatives to explore the regulation of fluorescence properties by introducing electron-absorbing groups and electron donor groups. The application of 2-styrene-8-hydroxyquinoline as probe in metal ion detection was studied. This paper is divided into five chapters: the first chapter describes the application of zinc in human growth and development of 8-hydroxyquinoline compounds. Then, the generation of fluorescence, the factors affecting fluorescence and the luminescence mechanism of fluorescence probe are described. The application and research progress of 8-hydroxyquinoline derivatives are described. The design idea and research content of the thesis are put forward. The second chapter, experimental part. Six 2-styrene-8-hydroxyquinoline derivatives were prepared by two-step reaction, and their structures were characterized by NMR, NMR and MS spectra. In the third chapter, the complexes of six 2-styrene-8-hydroxyquinoline derivatives with Zn2 and Cd2 were measured by fluorescence and UV-Vis spectra. The conditions were as follows: water content, reaction time, concentration of metal ions and so on. By comparing the maximum emission wavelengths of these compounds, the effects of electron absorbent substituents and donor substituents on the fluorescence properties of these compounds were studied. The results show that the maximum emission wavelength of fluorescence tends to red shift when the electron group is introduced, whereas the blue shift trend of the maximum emission wavelength of fluorescence can be observed by introducing the donor group. The fluorescence spectra and UV-Vis spectra of six 2-styrene-8-hydroxyquinoline derivatives were measured and compared with their metal ion complexes. The results show that the effect of electron effect is consistent. In chapter 4, we choose 2-4-methylphenylidene-8-hydroxyquinoline as a probe for cell imaging. The results of fluorescence microscope showed that only a very weak green fluorescence was observed in the dark field image after the probe was added into the cell. When the metal zinc ion was added further, the yellow fluorescence could be observed. Chapter V, the full text summary. The results show that solvent (external environment) and substituent (molecular structure) all affect the electron cloud density of the molecule. When the probe is coordinated with metal zinc ion and cadmium ion, not only the electron cloud density of the system is changed, but also the rigidity of the molecular plane is strengthened, both of which lead to the regular change of the fluorescence spectrum of the complex.
【学位授予单位】：东华大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O626.323

【相似文献】