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A Class of Fluorescent Compounds and Its Application in Detection of Ruthenium

A fluorescent compound and fluorescence technology, applied in the field of fluorescent compounds, can solve the problems of high cost, complex sample pretreatment process, difficult to popularize and apply, etc.

Active Publication Date: 2014-10-29
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these methods usually require large-scale analysis and detection instruments, complicated sample pretreatment process, and require specially trained personnel to operate, making these detection methods very expensive and difficult to popularize and apply. Fluorescent molecular sensors are gradually becoming a cheap and simple method. Methods

Method used

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  • A Class of Fluorescent Compounds and Its Application in Detection of Ruthenium
  • A Class of Fluorescent Compounds and Its Application in Detection of Ruthenium
  • A Class of Fluorescent Compounds and Its Application in Detection of Ruthenium

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Experimental program
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Effect test

Embodiment 1

[0056] The synthetic method of embodiment 1 compound 1

[0057] Under the condition of nitrogen protection, add 3g of DMF (2,7-dichlorofluorescein), 2.6g of anhydrous potassium carbonate and 40mL of dry DMF into a dry 100mL single-necked bottle, add a magnet, and heat and stir in an oil bath at 50°C , then add 2.26mL allyl bromide under the protection of nitrogen, continue to stir for 12 hours and stop the reaction, add 250mL deionized water after cooling, then extract three times with 300ml ethyl acetate, the collected organic phase is washed with water and saturated with chlorine Wash with sodium chloride solution, dry the organic phase over anhydrous sodium sulfate, filter, rotary evaporate, and recrystallize the product with n-hexane to finally obtain 2.8 g of orange-red compound 1 as a solid, with a yield of 80%. Chemical equations are shown in figure 1 middle.

Embodiment 2

[0058] The synthetic method of embodiment 2 compound 2

[0059]Add 1g of compound 1, 0.66g of sodium hydroxide and 40mL of tetrahydrofuran into a dry 100mL single-necked bottle, add a magneton and heat and stir in an oil bath at 70°C for 6 hours, adjust the pH to 1 with 3M dilute hydrochloric acid after cooling, and then use 30 mL of ethyl acetate was extracted, the organic phase was washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and rotary evaporated. The crude product was purified by column chromatography to obtain 450 mg of a yellow-white product. Chemical equations are shown in figure 1 middle. 1 H NMR (400MHz, CDCl 3 ,293K)δ8.12–8.01(dd,1H),7.79–7.60(m,2H),7.20–7.12(m,1H),6.97–6.89(m,1H),6.85–6.78(m,1H), 6.76–6.68(m,2H),6.16–5.98(m,1H),5.50(dd,J=17.3,1.4Hz,1H),5.37(dd,J=10.6,1.3Hz,1H),4.67(d, J=5.0Hz,2H).

Embodiment 3

[0060] The synthetic method of embodiment 3 compound 3

[0061] Under the condition of nitrogen protection, 150 mg of potassium tert-butoxide and 300 mg of compound 2 were added to a 100 mL single-necked bottle, and finally 10 mL of DMSO was added, and a magnet was added and heated and stirred in an oil bath at 80°C for 12 hours. After cooling, adjust the pH to 1 with 3M dilute hydrochloric acid, then add 50 mL of deionized water, extract with 30 mL of ethyl acetate, wash the organic phase with water and saturated brine, dry over anhydrous sodium sulfate, filter, and rotary evaporate, and the crude product is passed through the column Purified by chromatography to finally obtain 45 mg of yellow product. Chemical equations are shown in figure 1 middle. 1 H NMR (400MHz, CDCl 3 ,293K)δ8.07(d,J=7.2Hz,1H),7.71(ddd,J=19.0,11.1,6.9Hz,2H),7.17(d,J=7.4Hz,1H),6.92(d,J =6.5Hz,2H),6.77(s,1H),6.72(s,1H),6.47–6.31(m,1H),5.20–5.07(m,1H),1.74(dd,J=6.9,1.6Hz, 3H). 13 C NMR (101MHz, CDCl ...

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Abstract

The invention discloses a fluorescent compound with a general formula I structure, and additionally relates to a method for detecting ruthenium metal in a sample by utilizing the fluorescent compound described in the general formula I. The method comprises the following steps of: (1) providing an appropriate pH system for the sample; (2) mixing the following detection solution and the sample, wherein the detection solution is composed of the components of a fluorescent compound I, an oxidizing agent and a cosolvent acetonitrile; and (3) detecting the fluorescence intensity of the sample after mixing so as to obtain the ruthenium metal content in the sample. The principle is that Ru in the sample is oxidized into RuO4 through an oxidizing material, then olefin in a fluorogen is oxidized into carboxylic acid by the RuO4, and finally a carboxylic acid structure is removed in a mode of CO2, gama-butyrolactone or delta-valerolactone, so that the fluorescence is enhanced. The method can detect the low ruthenium content in the sample, and the method has a wide ruthenium application prospect.

Description

technical field [0001] The present invention relates to a class of fluorescent compounds that enable them to be used as probes to detect various ruthenium-containing reagents, such as Ru 3+ and Grubbs second-generation catalysts. Background technique [0002] Due to the importance of metal elements in biological systems and the difficulty of their detection in living cells, it is particularly important to apply fluorescence technology to the detection of metals. Some fluorescence detection systems are capable of detecting analytes from real samples in the environment. In addition, because of the rapidity and reproducibility of fluorescence detection methods, it has become very important in many screening applications. [0003] For example, ruthenium metal is widely used in chemistry, medicine and other materials. In the process of organic synthesis, because of the very convenient formation of carbon-carbon double bonds, the ruthenium-catalyzed olefin metathesis reaction h...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/82C09K11/06G01N21/64
Inventor 宋锋玲陈博彭孝军
Owner DALIAN UNIV OF TECH
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