香豆素衍生物荧光探针的设计、合成及对金属离子识别性能的研究

发布时间：2018-06-08 02:07

  本文选题：荧光分子探针 + 香豆素　； 参考：《河北大学》2016年硕士论文

【摘要】：金属离子与生命科学、环境科学和医学等领域联系紧密,选择性识别和检测一些环境和生物体中常见的金属离子具有重要作用。荧光分子探针具有选择性高、灵敏性好,操作方法简单,可实时监测等优点,因此被广泛应用于金属离子的检测。本文结合香豆素荧光团受体的研究现状及其发展趋势,设计了可以识别金属离子的探针,并且进行了深入研究。设计、合成了三种在香豆素的3位以酰胺键连接不同链长苯基硫脲的Fe~(3+)荧光探针A1-A3。通过金属离子滴定试验,发现该类探针对Fe~(3+)离子具有明显的识别作用,其它常见的金属离子对其无明显影响。7-二乙氨基香豆素-3-(N-(2-(3-苯基硫脲)己基))甲酰胺(A3)对Fe~(3+)的淬灭率高达99.2%。设计、合成了硫脲直接连接在香豆素3位上的金属离子探针B1-B4。在乙腈溶剂中,1-香豆素-3-苯基硫脲(B1)和1-(7-羟基)香豆素-3-苯基硫脲(B2)对Mg~(2+)有一定的选择性,对应的荧光光谱发生了蓝移,其它金属离子对其测试无影响。N-(香豆素-3-氨基硫代甲酰基)苯甲酰胺(B3)和N-((7-羟基)香豆素-3-氨基硫代甲酰基)苯甲酰胺(B4)在乙腈溶剂中可以专一识别Ag~(+),结合Ag~(+)后荧光增强。我们将吡啶基作为识别基团引入香豆素3位,同时考虑到金属离子的配位数不同和空间因素影响,合成了“单”和“双”吡啶基识别基团香豆素探针C1-C5。这五种探针可以在EtOH/HEPES(v/v=1:1)中选择性识别Fe~(3+),其中7-羟基-3-N,N-双2-吡啶甲胺基香豆素(C3)可以在乙腈和EtOH/HEPES(v/v=1:1)中分别识别Zn~(2+)和Fe~(3+),其它金属离子对其无影响。
[Abstract]:Metal ions are closely related to the fields of life science, environmental science and medicine, so selective recognition and detection of some common metal ions in environment and organism play an important role. Fluorescent molecular probes are widely used in the detection of metal ions due to their advantages of high selectivity, good sensitivity, simple operation and real-time monitoring. In this paper, based on the research status and development trend of coumarin fluorescent group receptors, a probe which can recognize metal ions has been designed and studied deeply. Three kinds of fluorescence probes A _ 1-A _ 3 were designed and synthesized, which were linked to phenythiourea with different chain length by amide-bond at three sites of coumarin. Through the metal ion titration test, it is found that this kind of probe has obvious recognition effect on the Fe ~ (2 +) ~ (3) ~ (3) ion. Other common metal ions have no significant effect on the effect. The quenching rate of Feanzao 3) is 99.2%. The quenching rate of 7- diethylaminocoumarin -3-diethylaminocoumarin (N-Con _ 2-N _ (2 -) -N ~ (-) (A3) is as high as 99.2%. A metal ion probe B1-B4 was designed and synthesized, which was directly connected to coumarin 3 position by thiourea. In acetonitrile solvent, 1-coumarin -3-phenylthiourea (B1) and 1-7-hydroxyl) coumarin (-3-phenylthiourea) B2) have a certain selectivity for MgN _ 2), and the corresponding fluorescence spectra have a blue shift. Other metal ions have no effect on its determination. N-( coumarin -3-aminothioformyl) benzoamide B _ 3 and N-Con 7-hydroxyl) coumarin -3-aminothioformyl) benzoamide B _ 4) can be specially identified in acetonitrile solvent. In this paper, we introduce pyridyl as recognition group into coumarin 3. Considering the different coordination number of metal ions and the influence of space factors, we synthesized the "single" and "bis" pyridine recognition group coumarin probe C1-C5. These five probes can be selectively identified in EtOH / HEPESV / v-1: 1). Among them, 7- hydroxyl -3-N- N- (2-pyridyl) coumarin C _ 3) can be identified in acetonitrile and EtOHHEPES / v1: 1, respectively.
【学位授予单位】：河北大学
【学位级别】：硕士
【学位授予年份】：2016
【分类号】：O657.3

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