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Multi-response azacyclo-formaldehyde fluorescent probe molecule as well as preparation method and application thereof

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

Active Publication Date: 2021-03-12
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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  • Multi-response azacyclo-formaldehyde fluorescent probe molecule as well as preparation method and application thereof
  • Multi-response azacyclo-formaldehyde fluorescent probe molecule as well as preparation method and application thereof
  • Multi-response azacyclo-formaldehyde fluorescent probe molecule as well as preparation method and application thereof

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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 azacyclo-formaldehyde fluorescent probe molecule with a structure shown as a formula I and a preparation method and application thereof, the molecule realizesselective quantitative recognition of formaldehyde through a fluorescence analysis method, and formaldehyde, copper ions and sulfur ions are tested and evaluated in the fields of automotive trim materials, healthy home furnishing, biological medicines and the like. The multi-response azacyclo-formaldehyde fluorescent probe molecule can be used for fluorescence imaging of biological samples, can also be used as an ultraviolet light absorber to be applied to the technical fields of plastics, coatings, printing ink, display, illumination, glasses, daily-use chemical industry, textiles and the like, and in addition, the multi-response azacyclo-formaldehyde fluorescent probe molecule provided by the invention has relatively strong fluorescence emission performance under both solution and solidconditions; can be used as a fluorescent material in the fields of anti-counterfeiting technologies, light conversion materials, fluorescence labeling, fluorescence imaging and the like, wherein R isH 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 Applications(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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