本文選題：有機(jī)小分子熒光探針　切入點(diǎn)：熒光增強(qiáng)　出處：《新疆大學(xué)》2017年碩士論文　論文類型：學(xué)位論文

【摘要】：近年來(lái),有機(jī)小分子熒光探針以其結(jié)構(gòu)簡(jiǎn)單、合成方便、選擇性高、靈敏度高和抗干擾能力突出等優(yōu)點(diǎn),而被廣泛應(yīng)用在檢測(cè)環(huán)境中各種有毒有害的重金屬陽(yáng)離子和陰離子污染物。此外,有機(jī)小分子熒光探針還可以在細(xì)胞和活體組織中實(shí)現(xiàn)熒光成像,對(duì)醫(yī)學(xué)領(lǐng)域有著非凡的意義。本論文利用常見檢測(cè)機(jī)理基于常用的熒光基團(tuán)設(shè)計(jì)合成了一系列熒光增強(qiáng)型(“turn on”)有機(jī)小分子熒光探針,并在水溶液體系下對(duì)劇毒陰離子CN~-和有毒有害的重金屬陽(yáng)離子Ag~+、Zn~(2+)以及Hg~(2+)進(jìn)行了檢測(cè)。本文將從以下研究?jī)?nèi)容展開:1.我們用4-(N,N-二苯胺基)苯甲醛、2-苯基-1,2,3-三唑基-4-甲醛、喹喔啉醛和1,2,3,3-四甲基-3-氫-吲哚VA碘化物發(fā)生Knoevenagel縮合反應(yīng),設(shè)計(jì)合成了三種簡(jiǎn)單的小分子M1、M2和M3,并成功的篩選出一種在水溶液中檢測(cè)CN~-的熒光增強(qiáng)型(“turn on”)有機(jī)小分子熒光探針M1。探針M1與CN~-基于親核加成反應(yīng)機(jī)理阻礙了M1分子的ICT效應(yīng)進(jìn)而由無(wú)熒光變?yōu)楹軓?qiáng)的藍(lán)色熒光并伴隨顏色由紫色變?yōu)闊o(wú)色。檢測(cè)限達(dá)到6.1×10-7 M,在混合溶劑為DMSO-H2O(3:2 v/v,Tris-HCl=50 mM,pH=7.0)測(cè)試條件下,探針M1對(duì)CN~-的識(shí)別具有快速響應(yīng)(1min)、選擇性專一、靈敏度高和抗干擾性強(qiáng)且可以裸眼識(shí)別等優(yōu)點(diǎn)。另外,在不同水樣中對(duì)CN~-的檢測(cè)中發(fā)現(xiàn),探針M1有應(yīng)用于真實(shí)的水體環(huán)境體系檢測(cè)CN~-的可能性。我們?yōu)闄z測(cè)CN~-提供了一種新型高選擇性、高靈敏度、強(qiáng)的抗干擾性的熒光探針傳感器。2.我們用4-(N,N-二苯胺基)苯甲醛和4-氨基-5-苯基-4-氫-1,2,4-三唑基-3-硫醇進(jìn)行反應(yīng),成功合成了熒光增強(qiáng)型有機(jī)小分子熒光探針M4。首先,在DMSO溶液中探針M4對(duì)Ag~+進(jìn)行了檢測(cè),表現(xiàn)出非常好的熒光響應(yīng)行為,M4檢測(cè)Ag~+具有很高的靈敏性和很好的抗干擾能力,其檢測(cè)限為2.7×10-7 M。其次,體系在混合溶劑EtOH-H2O(1:1 v/v,HEPES=50 mmol,pH=7.4)中,探針M4對(duì)Ag~+也表現(xiàn)出非常好的熒光響應(yīng)行為,且具有很高的靈敏性和很好的抗干擾能,檢測(cè)限為7.5×10-7 M。最后,體系在混合溶劑EtOH-H2O(1:1 v/v,Tris-HCl=50 mM,pH=7.0)中探針M4對(duì)Zn~(2+)的檢測(cè)表現(xiàn)出非常好的熒光響應(yīng)行為,檢測(cè)限為2.35×10-7 M。另外,探針M4在Hela細(xì)胞中實(shí)現(xiàn)了對(duì)Ag~+及Zn~(2+)的識(shí)別。3.基于羅丹明結(jié)構(gòu)設(shè)計(jì)合成了一種比色熒光雙通道檢測(cè)Hg~(2+)的熒光增強(qiáng)型有機(jī)小分子熒光探針M5。體系在混合溶劑EtOH-H2O(1:1 v/v,HEPES=50 mM,pH=7.0)中,探針M5對(duì)Hg~(2+)的檢測(cè)具有高的靈敏性和很好的抗干擾能力,檢測(cè)限為1.73×10-8 M。另外,在不同水樣中對(duì)Hg~(2+)的檢測(cè)中發(fā)現(xiàn),探針M5有應(yīng)用于真實(shí)的水體環(huán)境體系檢測(cè)Hg~(2+)的可能性。我們?yōu)闄z測(cè)Hg~(2+)提供了一種新型高選擇性、高靈敏度、強(qiáng)的抗干擾性的熒光增強(qiáng)型有機(jī)小分子熒光探針。
[Abstract]:In recent years, organic small molecule fluorescence probe has the advantages of simple structure, convenient synthesis, high selectivity, high sensitivity and outstanding anti-interference ability. It has been widely used to detect various toxic and harmful heavy metal cations and anionic pollutants in the environment. In addition, fluorescence probes of small organic molecules can also be used for fluorescence imaging in cells and living tissues. In this paper, a series of fluorescence probes of "turn on" organic molecules were designed and synthesized based on common fluorescent groups. The highly toxic anions CN- and the toxic and harmful heavy metal cations Ag2 and Hg~(2) were determined in aqueous solution system. In this paper, the following research contents were carried out: 1. We use 4-N- N- (N-diphenylamino) benzaldehyde, 2-phenyl-1-triazol-2-triazol-4-formaldehyde. The Knoevenagel condensation reaction between quinoxaldehydes and 3-tetramethyl-3-hydro-indole VA iodides was observed. Three simple small molecules M _ 1M _ 2 and M _ 3 were designed and synthesized, and a fluorescence enhanced organic fluorescence probe ("turn on") was successfully selected for the detection of CNN- in aqueous solution. The reaction mechanism of probe M1 and CN-based on nucleophilic addition hinders M1. The ICT effect of the molecule then changed from non-fluorescence to strong blue fluorescence and accompanied by color change from purple to colorless. The detection limit was 6.1 脳 10 ~ (-7) M, and the pH value of the mixed solvent was DMSO-H2O(3:2 v / v ~ (-1) Tris-HCln ~ (50) Mm ~ (1) (pH = 7.0), and the detection limit was 6.1 脳 10 ~ (-7) M ~ (-1). Probe M1 has the advantages of fast response, selectivity, high sensitivity, strong anti-interference, and can be recognized by naked eyes. In addition, it is found in different water samples. Probe M1 has the potential to be used in real water environmental systems to detect CNN-. We have provided a new type of high selectivity and high sensitivity for the detection of CN-. Fluorescence probe sensor with strong anti-interference. We have successfully synthesized fluorescence probe M4-, a fluorescence enhanced organic small molecule, by the reaction of 4-Amino-5-Phenyl-4-Hydro-1-triazol-3-mercaptan and 4-Amino-N- (N-diphenylaminyl) benzaldehyde. The probe M4 was used to detect Ag~ in DMSO solution. The fluorescence response behavior of M4 was very good. The detection limit of M4 was 2.7 脳 10 ~ (-7) M4. Secondly, in the mixed solvent EtOH-H2O(1:1 v / vvHEPES ~ (50 mmol / L), the pH value of the system was 7.4, and the detection limit was 2.7 脳 10 ~ (-7) M4. The probe M4 also showed a very good fluorescence response to Ag ~, and had high sensitivity and good anti-interference ability. The detection limit was 7.5 脳 10 ~ (-7) M. finally, the detection limit of M4 was 7.5 脳 10 ~ (-7) m, and the detection limit was 7.5 脳 10 ~ (-7) M. The fluorescence response of probe M4 to Zn~(2 was very good in the mixed solvent EtOH-H2O(1:1 v / v / Tris-HCln (50 mMg pH = 7.0), and the detection limit was 2.35 脳 10 ~ (-7) M. in addition, the detection limit was 2.35 脳 10 ~ (-7) M ~ (-1) 路mol ~ (-1) 路L ~ (-1). The probe M4 has realized the recognition of Ag- and Zn~(2 in Hela cells. (3) based on Rhodamine structure, a fluorescence enhanced fluorescence probe M5 for small organic molecules was designed and synthesized based on the structure of Rhodamine. The detection limit of probe M5 for Hg~(2 is 1.73 脳 10 ~ (-8) M.The detection limit of M5 is 1.73 脳 10 ~ (-8) M. in addition, the detection of Hg~(2 in different water samples has been found. The probe M5 has the potential to be applied to the detection of Hg~(2 in real water environment system. We have provided a novel fluorescence enhanced fluorescence probe with high selectivity, high sensitivity and strong anti-interference for detecting Hg~(2.
【學(xué)位授予單位】：新疆大學(xué)
【學(xué)位級(jí)別】：碩士
【學(xué)位授予年份】：2017
【分類號(hào)】：O657.3

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