含2-氨基苯酚、2-氨基苯硫酚类化合物的合成及其性能研究

发布时间：2018-03-17 19:36

本文选题：荧光探针　切入点：2-氨基苯酚　出处：《新疆大学》2017年硕士论文　论文类型：学位论文

【摘要】：本论文主要利用三苯胺基和三唑基为荧光发色团,2-氨基苯酚中的氧原子和氮原子为螯合基团,亚胺为桥连基团,设计并合成了两种铜离子和一种铁离子小分子荧光探针,发现一种较为温和的合成苯并噻唑化合物的方法,并对它们的光学性质进行了研究,主要内容如下:1.设计并合成了一种基于C=N异构化机理的“turn-on”型Cu~(2+)荧光探针(E)-2-((4-(二苯基氨基)亚苄基)氨基)苯酚M1。经研究发现,探针M1本身无荧光,但当Cu~(2+)存在时,M1的荧光强度发生了将近250倍的增强,荧光颜色由无色变为亮蓝色,在乙腈溶液和水性介质中检测限分别为1.8×10~(-7) M和8.5×10~(-7) M。探针M1实现了在CH3CN和水性介质体系中对Cu~(2+)的优异检测。2.通过简单的缩合反应合成了一种“turn-on”型Fe~(3+)探针(E)-2-(((2-苯基-2H-1,2,3-三唑-4-基)亚甲基)氨基)苯酚(M2)。经进一步研究发现,向探针M2的溶液中加入Fe~(3+)后,该探针由无色溶液变为了黄色,荧光由几乎没有荧光变为蓝色荧光,同时表现出优异的抗干扰性能,Fe~(3+)的检测限为4.7×10~(-7) M。并进一步通过高分辨质谱实验对探针M2和Fe~(3+)的作用机制进行了探究。3.利用简单的生成席夫碱的缩合反应成功合成了荧光探针M3,并对其光学性能和离子识别性能进行了系统研究。实验结果表明,当向M3的CH3CN溶液中加入Cu~(2+)后,溶液由弱荧光变为黄色的强荧光(检出限为6.395×10~(-7) M)。4.以三苯胺醛和三唑醛分别为原料在乙醇为溶剂回流条件下与2-氨基苯硫酚合成了两种苯并噻唑类化合物M4、M5。经研究,发现M5在不同极性溶剂中,表现出不同的光谱属性,随着溶剂极性的增加探针最大发射峰发生了明显的红移,且均具有较高的荧光量子产率。同时对其离子识别性能进行研究时发现,PA(苦味酸)可以使该探针发生明显的荧光淬灭(检出限1.6×10~(-7) M)。
[Abstract]:This paper mainly uses three aniline and three triazole based fluorescent chromophore, oxygen atom and nitrogen atom in the 2- aminophenol chelate group, imine as bridging groups, and design two kinds of copper ion and iron ion of a small molecule fluorescent probe was synthesized and found a more moderate approach to benzo thiazole compounds, and their optical properties were studied. The main contents are as follows: 1. design and synthesis of a C=N based on the isomerization mechanism of "turn-on" type Cu~ fluorescent probe (2+) (E) (-2- (4- (two amino phenyl) benzyl) amino phenol) M1. the study found that the probe M1 has no fluorescence, but when Cu~ (2+) exists, has enhanced nearly 250 times the M1 fluorescence intensity, fluorescence color change from colorless to light blue, in acetonitrile and in aqueous medium, the detection limits were 1.8 * 10~ (-7) M and 8.5 * 10~ (-7) M. probe M1 the realization of the CH3CN and water On the Cu~ medium (2+) a "turn-on" type Fe~ was synthesized by the condensation reaction of the excellent detection of.2. simple probe (3+) (E) (-2- ((2- -2H-1,2,3- three -4- phenyl triazole) Ya Jiaji) amino) phenol (M2). After further study found that adding Fe~ to the solution probe in M2 (3+), the probe is composed of a colorless solution turns to yellow fluorescence by almost no fluorescence into blue fluorescence, while exhibiting excellent anti-interference performance, Fe~ (3+) and the detection limit is 4.7 * 10~ (-7) M. and further by high resolution mass spectrometry experiments to probe M2 and Fe~ (3+) the mechanism of synthesis of M3 fluorescent probe into.3. condensation reaction using simple form a Schiff base, and the optical properties and ion recognition properties were studied. The experimental results show that when adding Cu~ to CH3CN solution of M3 (2+), fluorescence from weak solution yellow Qiang Yingguang (Frederick The limit is 6.395 * 10~ (-7) M).4. with three aniline aldehyde and three triazole aldehyde were two kinds of benzothiazole compounds M4 synthesized in ethanol solvent under reflux conditions for 2- and p-amino-benzenethiol, M5. through research, found that M5 in different polar solvents, showed different spectral properties with the increase of solvent polarity probe emission peak has obvious red shift, and the fluorescence quantum yield were high. At the same time found to study the ion recognition performance, PA (picric acid) can make the obvious fluorescence quenching probe (detection limit of 1.6 * 10~ (-7) M).

【学位授予单位】：新疆大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O657.3

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