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A kind of imidazo[1,5-a]pyridine dye and its synthesis method and application

A 5-a, pyridine-based technology, applied in the field of organic fluorescent fluorescent probe synthesis, can solve the problems of long time response, low sensitivity, complicated operation, etc., and achieve the effects of high sensitivity, good selectivity and simple synthesis process

Active Publication Date: 2022-01-04
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these methods are complicated to operate, have a long time response, low sensitivity, and are expensive

Method used

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  • A kind of imidazo[1,5-a]pyridine dye and its synthesis method and application
  • A kind of imidazo[1,5-a]pyridine dye and its synthesis method and application
  • A kind of imidazo[1,5-a]pyridine dye and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Add 2-benzoylpyridine (2.0mmol, 0.3661g), salicylaldehyde (3.0mmol, 0.3662g) and ammonium acetate (10.0mmol, 0.7705g) sequentially into a 50mL reaction bottle, stopper the bottle tightly, and inject 10mL Glacial acetic acid solution was reacted for 5 h under reflux under nitrogen atmosphere. Reaction TLC monitors to end, adds 100mL distilled water, dichloromethane extracts 3 times (each 30mL), merges organic phase, anhydrous sodium sulfate drying, removes solvent under reduced pressure, with column chromatography (eluent is: V acetic acid Ethyl ester / V petroleum ether=1:4) isolated to obtain 2-(1-phenylimidazo[1,5-a]pyridin-3-yl)phenol, light gray solid product (0.2804g, yield 49% ), its chemical structure is:

[0033]

[0034] The 2-(1-phenylimidazo[1,5-a]pyridin-3-yl)phenol obtained in Example 1 is carried out nuclear magnetic spectrum analysis, and the results are as follows: 1 H NMR (500MHz, CDCl 3 )δ12.01(s,1H),8.53(d,J=7.3Hz,1H),7.90(d,J=8.3Hz,3H),7.78(d,J=6.6...

Embodiment 2

[0036] Add 2-benzoylpyridine (2.0mmol, 0.3661g), 4-methoxysalicylaldehyde (3.0mmol, 0.4562g) and ammonium acetate (10.0mmol, 0.7705g) successively into a 50mL reaction flask, stopper Stopper the bottle, inject 10mL of glacial acetic acid solution, and react for 5h under reflux conditions. Reaction TLC monitors to end, adds 100mL distilled water, dichloromethane extracts 3 times (each 30mL), merges organic phase, anhydrous sodium sulfate drying, removes solvent under reduced pressure, with column chromatography (eluent is: V acetic acid Ethyl ester / V petroleum ether=1:4) isolated to obtain 4-methoxy-2-(1-phenylimidazo[1,5-a]pyridin-3-yl)phenol, dark yellow solid product (0.3098g , yield is 49%), its chemical structural formula is:

[0037]

[0038] The 4-methoxyl group-2-(1-phenylimidazo[1,5-a]pyridin-3-yl)phenol that embodiment 2 obtains carries out nuclear magnetic spectrum analysis, and the results are as follows: 1 H NMR (500MHz, CDCl 3 )δ12.21(s,1H),8.44(d,J=7.4Hz,1H...

Embodiment 3

[0040] Add 2-benzoylpyridine (2.0mmol, 0.3661g), 4-diethylamino salicylaldehyde (3.0mmol, 0.5793g) and ammonium acetate (10.0mmol, 0.7705g) successively into a 50mL reaction flask, and stopper Stopper the bottle, inject 10mL of glacial acetic acid solution, and react for 5h under reflux conditions. Reaction TLC monitors to end, adds 100mL distilled water, dichloromethane extracts 3 times (each 30mL), merges organic phase, anhydrous sodium sulfate drying, removes solvent under reduced pressure, with column chromatography (eluent is: V acetic acid Ethyl ester / V petroleum ether=1:4) separated to obtain 2-(1-phenylimidazo[1,5-a]pyridin-3-yl)phenol as light yellow solid product (0.4143g, yield 58% ), its chemical structure is:

[0041]

[0042] The 4-diethylamino-2-(1-phenylimidazo[1,5-a]pyridin-3-yl)phenol that embodiment 3 obtains carries out nuclear magnetic spectrum analysis, and the results are as follows: 1 H NMR (500MHz, CDCl 3 )δ12.06(s,1H),8.43(d,J=7.4Hz,1H),7.89(d,J...

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Abstract

The invention discloses an imidazo[1,5-a]pyridine dye and its synthesis method and application. The chemical structural formula of the imidazo[1,5-a]pyridine dye is shown in formula (III): In formula (Ⅲ), R is selected from H, C 1 ~C 16 Alkyl, C 1 ~C 16 One of alkoxy, nitro, monoalkyl substituted amine or dialkyl substituted amine; the alkyl in the monoalkyl substituted amine or dialkyl substituted amine The number of carbon atoms is 1~16. The functional molecular imidazo[1,5-a]pyridine dyes of the present invention have the characteristics of simple preparation method, energy saving and high fluorescence quantum yield, and can be applied to Cu 2+ The detection has high sensitivity and high selectivity, and is suitable for application in the fields of fluorescent dyes, fluorescent sensors and biological imaging.

Description

technical field [0001] The invention relates to the field of synthesis of organic fluorescent fluorescent probes, in particular to an imidazo[1,5-a]pyridine dye and its synthesis method and application. Background technique [0002] Cu 2+ It is closely related to our life. Although it is not an important rare element in the human body, it plays a very important role in the human body. Its main function is to assist hematopoiesis, that is, to catalyze the synthesis of hemoglobin. But when Cu in the body 2+ Too little can cause a series of diseases, such as alopecia, albinism, vitiligo and osteoporosis. Traditionally used to detect Cu 2+ The technical means include voltammetry, inductively coupled plasma atomic emission spectrometry, atomic absorption spectrometry, etc. However, these methods are complicated to operate, have long time response, low sensitivity, and are expensive. Compared with traditional techniques, the method of detecting metal ions with fluorescent pr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04C09B57/00C09K11/06G01N21/64
CPCC07D471/04C09B57/00C09K11/06G01N21/6428C09K2211/1044
Inventor 李郁锦薛帅高建荣
Owner ZHEJIANG UNIV OF TECH
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