Benzimidazole quinoline derivative and preparation method and application

A technology of benzimidazoquinoline and benzimidazole, applied in the field of analytical chemistry, can solve the problems of slow sample detection, unsuitable for on-site detection or large-scale popularization and application, complex sample pretreatment process, etc., and achieves easy operation and detection method. Diverse and complex effects

Active Publication Date: 2016-06-15
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing conventional detection methods require expensive large-scale instruments, complicated sample pretreatment processes, and professional operations by professional technicians.
Therefore, there is a slow sample detection, which is not suitable for on-site detection or large-scale promotion and application

Method used

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  • Benzimidazole quinoline derivative and preparation method and application
  • Benzimidazole quinoline derivative and preparation method and application
  • Benzimidazole quinoline derivative and preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0034] (A) Preparation of 2-methyl-8-(2-benzimidazolyl) quinoline (1)

[0035] After mixing 2-methylquinoline-8-carboxylic acid (4.8620g, 26mol), double equivalent o-phenylenediamine (3.0888, 28.6mol) and polyphosphoric acid (26.3562, 78mol), stir and reflux for more than 6 hours, cool Finally, add the reaction solution into a beaker filled with a large amount of water, adjust the pH to neutral with ammonia water, stir, solids precipitate out, filter with suction, recrystallize with 60% ethanol, the yield is 70.54%, and the melting point is 173.5-174.3°C. Nuclear Magnetic Resonance Spectrum Proton 1H NMR (400MHz, CDCl3): δ: 13.72(br,1H),9.11(d,1H),8.16(d,1H),7.86(d,2H),7.65(t,2H),7.39 (d, 1H), 7.29-7.31 (m, 2H), 2.91 (s, 3H).

[0036] (B) 2-(4-N,N-Dimethylstyryl)-8-(1H-benzimidazole)quinoline (copper ion fluorescent probe)

[0037] Add 2-methyl-8-benzimidazolylquinoline (0.8750g, 3.38mmol), N,N-dimethylbenzaldehyde (2.0210g, 13.5mmol) into a 50mL two-necked bottle, and under...

Embodiment 2

[0039]Preparation procedure of the test solution: in a 10mL sample bottle, add 5.0mL double distilled water, then add 0.1mol / L Cu2+ standard solution (20μL, 20eq), then add 5.0mL acetonitrile, mix well (pH=6.40) ; Finally, add 100 μL of 1×10-3 probe BMQS in acetonitrile solution and mix again. After standing for 10 minutes, the ultraviolet absorption and fluorescence emission were measured at 420nm as the excitation wavelength. The above operation, without adding metal ion solution, is the preparation of blank test solution. Measure UV absorption and fluorescence emission.

[0040] UV spectrum and fluorescence spectrum: The blank test solution of probe BMQS has strong absorption at 418nm and no absorption at 550nm; when copper ions exist, the absorption at 418nm is significantly weakened, and the absorption at 550nm is significantly enhanced, see Figure 7 . The blank test solution of probe BMQS has a strong fluorescence emission peak at 610nm. After adding copper ions, the...

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Abstract

The invention provides a benzimidazole quinoline derivative, a preparation method and application in copper ion detection, and particularly relates to a 2-(4-N,N-bis-substituted styryl)-8-1H-benzimidazole) quinoline derivative. Particularly, 2-aminobenzoic acid is used for preparing 2-methylquinoline-8-carboxylic acid, then the 2-methylquinoline-8-carboxylic acid and o-phenylenediamine are subjected to condensation to obtain 2-methyl-8-(2-benzimidazolyl) quinoline, the 2-methyl-8-(2-benzimidazolyl) quinoline and N,N-bis-substituted benzaldehyde are subjected to condensation to obtain the benzimidazole quinoline derivative. A probe has the good complexation with copper ions, when the copper ions exist, derivation of the solution is observed with naked eyes, and the solution is changed from yellow to purple, absorption at the 418 nm position on an ultraviolet visible absorption spectrum is weakened, and a novel absorption peak appears at the 550 nm and gradually increases when the concentration of the copper ions is increased; the benzimidazole quinoline derivative can be used for real-time and rapid measurement of complex samples and can also be used for semiquantitative detection of micro/trace Cu2+ of environment samples from different sources.

Description

technical field [0001] The invention belongs to the technical field of analytical chemistry, and relates to a benzimidazole quinoline derivative and a synthesis method thereof, which are applied to copper ion fluorescent agents. Background technique [0002] Copper is an important transition metal element in living organisms. It is the active ingredient of more than 30 enzymes and plays a very important role in the metabolism of living organisms. In living organisms, copper mainly exists in the form of Cu2+. Too much or too little Cu2+ in the human body will cause many diseases, such as Alzheimer's disease, Parkinson's disease, Menkes' syndrome, Wilson's syndrome, etc., which will endanger human health. Copper is highly toxic to lower organisms and crops, and its concentration greater than 0.1-0.2mg / L (about 2μM) can kill fish. The World Health Organization stipulates that, considering its toxicity, 1.5mg / L (about 25μM) is the maximum concentration allowed for copper ions ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04C09K11/06G01N21/64G01N21/33
CPCC07D401/04C09K11/06C09K2211/1007C09K2211/1029C09K2211/1044G01N21/33G01N21/643G01N2021/6432
Inventor 但飞君刘璐璐刘文俊廖全斌
Owner CHINA THREE GORGES UNIV
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