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A kind of multi-response nitrogen-heterocyclic formaldehyde fluorescent probe molecule and its preparation method and application

A fluorescent probe and nitrogen heterocycle technology is applied in the field of multi-responsive nitrogen heterocycle formaldehyde fluorescent probe molecules and their preparation, which can solve the problems of complex probe molecular structure, many preparation steps, slow response speed and the like, and achieve molecular structure The effect of stability, many recognition sites, and short response time

Active Publication Date: 2021-10-26
INST OF ANALYSIS GUANGDONG ACAD OF SCI (CHINA NAT ANALYTICAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although formaldehyde fluorescent probes have been paid attention to by researchers and extensive research has been carried out, there are still few varieties, and there are disadvantages such as complex molecular structure of the probe, many preparation steps, expensive reagents, and slow response speed. To meet the application requirements of formaldehyde testing and evaluation in materials, environments and complex systems, there is an urgent need to develop formaldehyde fluorescent probes with good biological stability, simple structure, easy preparation, fast response and good selectivity

Method used

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  • A kind of multi-response nitrogen-heterocyclic formaldehyde fluorescent probe molecule and its preparation method and application
  • A kind of multi-response nitrogen-heterocyclic formaldehyde fluorescent probe molecule and its preparation method and application
  • A kind of multi-response nitrogen-heterocyclic formaldehyde fluorescent probe molecule and its preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1: the preparation of probe molecule Ia

[0036]

[0037] (1) In a 100 ml round bottom flask, two (2-pyridyl) ketones (1mmol), methyl 4-formylbenzoate (1mmol) and ammonium acetate (10mmol) were dissolved in 30 ml of glacial acetic acid, Reflux reaction under rapid stirring for 9 hours; after the completion of the reaction, cool to room temperature, pour the reaction solution into ice water with stirring, adjust the pH=7 with ammonia water, filter the obtained solid under reduced pressure, wash with water 3 times, and wash the crude product with ethanol - recrystallization from acetone mixed solvent, and vacuum drying to obtain a yellow solid, which is intermediate IVa.

[0038] 1 H NMR (300MHz, CDCl 3 / TMS)δ:3.97(s,3H),6.71(t,J=7.5Hz,1H),6.93-6.99(m,1H),7.09-7.14(m,1H),7.70-7.76(m,1H) ,7.94-7.98(m,2H),8.15-8.31(m,4H),8.65(m,1H),8.75(d,J=7.5,Hz,1H); 13 C NMR (75MHz, CDCl 3 / TMS) δ: 52.28, 114.54, 120.04, 120.73, 121.51, 121.55, 122.06, 127.83, 129.94, ...

Embodiment 2

[0042] Preparation of probe molecule Ia

[0043] (1) In a 100 ml round bottom flask, dissolve bis(2-pyridyl)methanone (1mmol), methyl 4-formylbenzoate (1.2mmol) and ammonium acetate (17mmol) in 30 ml of glacial acetic acid , reflux reaction under rapid stirring for 7 hours; after the completion of the reaction, cool to room temperature, pour the reaction solution into ice water under stirring, adjust the pH=7 with 10wt% sodium hydroxide or potassium hydroxide aqueous solution, and filter the obtained solid under reduced pressure , washed with water for 3 times, the crude product was recrystallized from ethanol-acetone mixed solvent, and dried in vacuo to obtain intermediate IVa.

[0044] (2) In a 100 milliliter round bottom flask, intermediate IVa and hydrazine hydrate (mass concentration is 90wt%) were dissolved in 50 milliliters of ethanol at a weight ratio of 1:9, and refluxed for 7 hours under rapid stirring, and the reaction was completed After cooling to room temperatur...

Embodiment 3

[0046] UV-Vis Absorption and Fluorescence Properties Test of Probe Molecules

[0047] Compound Ia was formulated to a concentration of 1 × 10 -5 The N,N-dimethylformamide solution of M, measured the ultraviolet absorption and fluorescence properties on the HORIBA JobinYvonAqualog absorption and three-dimensional fluorescence scanning spectrometer with a 1 cm sample cell, the results are as follows Figure 2-4 shown.

[0048] Depend on figure 2 It can be seen that compound Ia has broadband strong absorption characteristics in the 270nm-430nm band, presents a strong absorption band, and has two absorption peaks, respectively located at 330nm and 366nm, the absorption wavelength of the maximum absorption peak is 366nm, and at greater than 430nm There is no obvious absorption in the above bands. Depend on image 3 It can be seen that in the spectral region greater than 430nm, the transmittance of the molecules is greater than 98%, and has good transparency. The results show ...

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Abstract

The invention discloses a multi-response azacyclic formaldehyde fluorescent probe molecule with the structure shown in formula I and its preparation method and application. The molecule realizes the selective and quantitative recognition of formaldehyde through the fluorescence analysis method, and is used in automotive interior materials, health Carry out testing and evaluation of formaldehyde, copper ions and sulfide ions in the fields of home furnishing, biomedicine, etc. It can also be used for fluorescence imaging of biological samples, and can also be used as an ultraviolet absorber for plastics, coatings, inks, displays, lighting, glasses, daily use Chemical industry, textiles and other technical fields, in addition, the multi-responsive azacyclic formaldehyde fluorescent probe molecule provided by the present invention has strong fluorescence emission performance in solution and solid state, and can be used as a fluorescent material for anti-counterfeiting technology, light conversion Materials, fluorescent labels, fluorescent imaging, etc.: wherein, R is H or Cl, and X is CH or N.

Description

Technical field: [0001] The invention relates to the technical field of organic functional material synthesis and analysis and testing, in particular to a multi-response azacyclic formaldehyde fluorescent probe molecule and a preparation method thereof. Background technique: [0002] Green travel, healthy home decoration, and beautiful living have become a new form of consumption and are gradually recognized by people. Cars and homes are more closely related to people's daily life. Whether car materials and home decoration materials are environmentally friendly, the quality of the car and indoor air quality is directly related to the physical and mental health of consumers, and the problem of car and indoor air pollution It has become a hot spot that consumers generally pay attention to. [0003] Volatile organic compounds (VOCs) are organic volatiles with a boiling point between 50 and 260 °C. They are important factors affecting the quality of the car and indoor air, and ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04C09K11/06G01N21/64
CPCC07D471/04C09K11/06C09K2211/1044G01N21/6428G01N21/6447G01N21/6456G01N2021/6439
Inventor 孙一峰王建业魏俊锋林梓榕刘海峰
Owner INST OF ANALYSIS GUANGDONG ACAD OF SCI (CHINA NAT ANALYTICAL
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