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8-benzimidazole quinoline derivative ratiometric pH probe and its preparation method and application

A technology of benzimidazole and derivatives, which is applied in the field of analytical chemistry, can solve the problems of external environment, probe load and retention, etc., which can affect the accuracy of results, achieve good selectivity, overcome electrochemical interference, and respond quickly Effect

Active Publication Date: 2019-01-15
CHINA THREE GORGES UNIV
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

But at the same time, the accuracy of the results is easily affected by factors such as external environment, detection substrate and photobleaching, probe loading and retention.

Method used

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  • 8-benzimidazole quinoline derivative ratiometric pH probe and its preparation method and application
  • 8-benzimidazole quinoline derivative ratiometric pH probe and its preparation method and application
  • 8-benzimidazole quinoline derivative ratiometric pH probe and its preparation method and application

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Embodiment 1

[0026] Example 1 Synthesis of pH fluorescent probe 2-p-hydroxystyryl-8-(1H-benzimidazole) quinoline

[0027] This embodiment provides the synthetic method of 2-p-hydroxystyryl-8-(1H-benzimidazole) quinoline, and its main steps are as follows:

[0028] Add 1.04g (4.015mmol) 2-methyl-8-(1H-benzimidazole) quinoline, 0.57g (4.672mmol) p-hydroxybenzaldehyde, 20mL absolute ethanol, and 1.6mL piperidine to the 50mL two-necked bottle successively , 0.9mL of glacial acetic acid, heated and stirred under reflux for 4 hours, cooled, a yellow solid precipitated out, filtered with suction, recrystallized from ethanol and dichloromethane, and obtained 1.24g of the product, with a yield of 85.40%. 1 HNMR (400MHz, DMSO) δ13.40(s, 1H), 9.93(s, 1H), 8.93(dd, J=7.4, 1.3Hz, 1H), 8.50(d, J=8.8Hz, 1H), 8.17( d, J=8.8Hz, 1H), 8.14–8.06(m, 1H), 7.93(d, J=7.1Hz, 1H), 7.85(t, J=12.4Hz, 2H), 7.80–7.68(m, 3H ),7.35–7.20(m,2H),6.91(d,J=8.6Hz,2H); 13 CNMR(101MHz,DMSO)δ159.11,157.66,151.00,145.04,143.30,...

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Abstract

The invention relates to a 8-benzimidazole substituted quinoline derivative and a preparation method and application thereof. The preparation method specifically comprises the steps of putting 2-methyl-8(1H-benzimidazol) quinoline and hydroxybenzaldehyde into a polar solvent, adding a catalyst, stirring and performing reflux reaction; after the reflux reaction, purifying to obtain the benzimidazole substituted quinoline derivative. The benzimidazol quinoline derivative provided by the invention is a ratio-type pH fluorescent probe, the probe shows wider pH response and has a better linear relationship in the range of 4.5 to 6.0, and the relative standard deviation is 0.993. In addition, the probe has better photochemical stability, has response to H<+> without the interference of metal ions, and has good reversibility. The probe has quick response to H<+>, and is high in sensitivity, and the pKa value is 4.69. The researches show that 2-hydroxylstyryl-8-benzimidazol quinoline is hopeful to become a novel ratio-type pH fluorescent probe.

Description

technical field [0001] The invention belongs to the technical field of analytical chemistry, and in particular relates to a quinoline derivative containing double bonds, hydroxybenzene, and benzimidazole substitution, and a preparation method and application thereof. Background technique [0002] In the field of environmental detection and biology, pH value is an important indicator parameter. The pH value in cells plays an important role in the process of cell proliferation and apoptosis, enzyme catalytic activity, ion transport and muscle contraction. Small changes in intracellular pH may cause cell dysfunction and even induce certain diseases. At the same time, before the onset of certain diseases or when eroded by foreign pollutants, there will also be fluctuations in the pH value. Therefore, the detection of intracellular pH changes plays an important role in the study of the physiological and pathological processes of cells. [0003] The glass electrode method is a c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/04C09K11/06G01N21/64
CPCC07D401/04C09K11/06C09K2211/1044G01N21/64
Inventor 但飞君韩雅莲郑星星刘璐璐贺顺龙
Owner CHINA THREE GORGES UNIV
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