Preparation method and application of benzimidazobenzisoquinolinone silyl ether

A technology of benziisoquinolinone and benzimidazole, which is applied to the application of detecting fluoride ions, the field of preparation of reactive fluoride ion molecular probes, and can solve problems such as blood pressure drop, mitochondrial dysfunction, and immune system metabolic disorders. , to achieve the effect of easy control of conditions, simple preparation process and good linear relationship

Inactive Publication Date: 2017-04-19
UNIV OF JINAN
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, high-concentration fluoride intake is very harmful to the human body. In mild cases, it will affect the growth and development of teeth and bones, and chronic fluorosis symptoms such as bone fluoride and dental fluorosis will appear. In severe cases, it will cause arrhythmia, nausea, Vomiting and other acute fluorosis
Excessive fluoride ions can inhibit the synthesis of protein and DNA, which makes

Method used

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  • Preparation method and application of benzimidazobenzisoquinolinone silyl ether
  • Preparation method and application of benzimidazobenzisoquinolinone silyl ether
  • Preparation method and application of benzimidazobenzisoquinolinone silyl ether

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Embodiment 1

[0022] Example 1: Synthesis of 3-(tert-butyldiphenyl)silyl-1,2-phenylenediamine (intermediate D1)

[0023] Weigh 0.46 g of 2,3-diaminophenol and 0.51 g of imidazole and dissolve them in 40 mL of dry dichloromethane solvent, then add 0.96 mL of tert-butyldiphenylchlorosilane to the solution, and react at room temperature for 48 hours. The reaction solution was concentrated and separated by column chromatography to obtain a light yellow oily liquid with a yield of 73%. NMR mass spectrometry is characterized as follows: 1 H NMR (400 MHz, CDCl 3 ) δ 7.85 (d, J = 6.5 Hz, 4H), 7.47 (dt, J = 14.0, 6.9 Hz, 6H), 6.44 (m, 2H), 6.10 (dd, J = 5.8, 3.6 Hz, 1H), 3.64 (s , 4H), 1.23 (s, 9H).

[0024] Synthesis of Molecular Probe D2

[0025] Weigh intermediate D1 (0.79g), 1,8-naphthalene dicarboxylic anhydride (0.39g) and 10mL glacial acetic acid into a 50mL round bottom flask, and reflux for 10h under nitrogen protection. After the reaction was complete, it was cooled to room tempera...

Embodiment 2

[0027] Probe molecule D2 (1×10 -5 M) in DMSO solution, the measured maximum absorption wavelength is 395nm, and the color is yellow. When F is added dropwise to the solution - (0-30equiv), the system produced a new ultraviolet absorption peak at a wavelength of 620nm, and the maximum absorption wavelength was red-shifted (225 nm). And with F - As the concentration increases, the absorption intensity increases all the time, until the fluoride ion concentration is 30 equiv of the probe concentration, the absorption intensity no longer increases (such as image 3 ), the color of the solution turns blue. Obviously, such a change in the maximum absorption wavelength is due to the breakage of the oxysilyl ether bond (R-O-Si) in the molecular probe and the transformation into an oxyanion (R-O-Si - );

Embodiment 3

[0029] Configuration 1×10 -5 M molecular probe solution, and then 3 equiv of different anions F were added to the solution - , Cl - ,Br - , I - , HSO 4 - , AcO - , H2 PO 4 - , ClO 4 - , to measure the ultraviolet absorption spectrum of the probe molecule in the presence of anions;

[0030] With reference to the ultraviolet absorption spectrum titration experiment of fluoride ion on the probe molecule, the present invention judges the selectivity of the probe to fluoride ion through the competition anion experiment, and adds 3 equiv of different anions F to the solution respectively. - , Cl - , Br - , I - , HSO 4 - ,AcO - , H 2 PO 4 - , ClO 4 - After that, the UV absorption spectrum did not change significantly. Under the same conditions, adding F - After (3equiv), the maximum absorption wavelength red-shifted by 225 nm, and the monitoring of the ultraviolet absorption intensity showed that the present invention is very suitable as a fluoride ion fluoresc...

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Abstract

The invention discloses a preparation method for a reaction type fluorine ion molecular probe. The preparation method is characterized in that a novel fluorine ion molecular probe based on benzimidazobenzisoquinolinone-12-silyl ether is prepared from 1,8-naphthalic anhydride, 2, 3-diaminophenol and tert-butyldiphenylsilane as raw materials. The molecular probe has the advantages of simple and convenient synthesis, mild reaction condition, easy purification, stable optical performance and the like. Oxygen-silicon bonds (R-O-Si) in the molecular probe can be broken through a specific reaction of probe molecules and fluorine ions in a DMSO medium, so that the probe molecules are transformed into negative oxygen ions (R-O-); the maximum absorption wavelength is subjected to red shift (225nm), so that the yellow color is changed to the blue color; the naked eyes can clearly distinguish the color change; and the absorption intensity and the fluorine ion concentration have a good linear relationship. High selectivity for the fluorine ions is expressed, the interference of other negative ions is avoided, and the response speed is high. The probe modules have important practical application values in the fields of biomedical chemistry, environmental science and the like.

Description

technical field [0001] The invention relates to the technical fields of environmental analysis and biological analysis and detection, in particular to a preparation method of a reactive fluoride ion molecular probe and an application of the molecular probe in detecting fluoride ions. Background technique [0002] Anions play important roles in many chemical and biological processes, so their identification and detection have received great attention in recent years. Among them, the identification and detection of fluoride ion is particularly important. Fluoride is an essential trace element for the human body. Adequate intake of fluoride can prevent dental caries and treat osteoporosis. However, high-concentration fluoride intake is very harmful to the human body. In mild cases, it will affect the growth and development of teeth and bones, and chronic fluorosis symptoms such as bone fluoride and dental fluorosis will appear. In severe cases, it will cause arrhythmia, nausea...

Claims

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Application Information

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IPC IPC(8): C07F7/18G01N21/33G01N21/78
CPCC07F7/1804C07F7/1892G01N21/33G01N21/78
Inventor 田忠贞钟志敏李冬梅
Owner UNIV OF JINAN
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