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香豆素衍生物熒光探針的設(shè)計(jì)、合成及對(duì)金屬離子識(shí)別性能的研究

發(fā)布時(shí)間:2018-06-08 02:07

  本文選題:熒光分子探針 + 香豆素 ; 參考:《河北大學(xué)》2016年碩士論文


【摘要】:金屬離子與生命科學(xué)、環(huán)境科學(xué)和醫(yī)學(xué)等領(lǐng)域聯(lián)系緊密,選擇性識(shí)別和檢測(cè)一些環(huán)境和生物體中常見(jiàn)的金屬離子具有重要作用。熒光分子探針具有選擇性高、靈敏性好,操作方法簡(jiǎn)單,可實(shí)時(shí)監(jiān)測(cè)等優(yōu)點(diǎn),因此被廣泛應(yīng)用于金屬離子的檢測(cè)。本文結(jié)合香豆素?zé)晒鈭F(tuán)受體的研究現(xiàn)狀及其發(fā)展趨勢(shì),設(shè)計(jì)了可以識(shí)別金屬離子的探針,并且進(jìn)行了深入研究。設(shè)計(jì)、合成了三種在香豆素的3位以酰胺鍵連接不同鏈長(zhǎng)苯基硫脲的Fe~(3+)熒光探針A1-A3。通過(guò)金屬離子滴定試驗(yàn),發(fā)現(xiàn)該類(lèi)探針對(duì)Fe~(3+)離子具有明顯的識(shí)別作用,其它常見(jiàn)的金屬離子對(duì)其無(wú)明顯影響。7-二乙氨基香豆素-3-(N-(2-(3-苯基硫脲)己基))甲酰胺(A3)對(duì)Fe~(3+)的淬滅率高達(dá)99.2%。設(shè)計(jì)、合成了硫脲直接連接在香豆素3位上的金屬離子探針B1-B4。在乙腈溶劑中,1-香豆素-3-苯基硫脲(B1)和1-(7-羥基)香豆素-3-苯基硫脲(B2)對(duì)Mg~(2+)有一定的選擇性,對(duì)應(yīng)的熒光光譜發(fā)生了藍(lán)移,其它金屬離子對(duì)其測(cè)試無(wú)影響。N-(香豆素-3-氨基硫代甲酰基)苯甲酰胺(B3)和N-((7-羥基)香豆素-3-氨基硫代甲;)苯甲酰胺(B4)在乙腈溶劑中可以專(zhuān)一識(shí)別Ag~(+),結(jié)合Ag~(+)后熒光增強(qiáng)。我們將吡啶基作為識(shí)別基團(tuán)引入香豆素3位,同時(shí)考慮到金屬離子的配位數(shù)不同和空間因素影響,合成了“單”和“雙”吡啶基識(shí)別基團(tuán)香豆素探針C1-C5。這五種探針可以在EtOH/HEPES(v/v=1:1)中選擇性識(shí)別Fe~(3+),其中7-羥基-3-N,N-雙2-吡啶甲胺基香豆素(C3)可以在乙腈和EtOH/HEPES(v/v=1:1)中分別識(shí)別Zn~(2+)和Fe~(3+),其它金屬離子對(duì)其無(wú)影響。
[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.
【學(xué)位授予單位】:河北大學(xué)
【學(xué)位級(jí)別】:碩士
【學(xué)位授予年份】:2016
【分類(lèi)號(hào)】:O657.3

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1 王姍姍;;小分子熒光探針在硫醇檢測(cè)中的最新研究進(jìn)展[J];科技信息;2010年23期

2 向雨秘;龍少波;朱R,

本文編號(hào):1993902


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