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A kind of salicylaldehyde hydrazine AIE compound and its preparation method and the application of constructing high luminous efficiency xerogel sensing film

A technology of high luminous efficiency and sensing thin film, which is applied in the field of supramolecular fluorescence detection, can solve the problems of low luminous efficiency of xerogel sensing thin film, late start of xerogel sensing thin film material, and influence on sensing performance, etc. , to achieve the effects of large-scale and cheap preparation, effective regulation and enhancement of fluorescence intensity, and rich molecular structure of compounds

Active Publication Date: 2021-10-26
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since the technology of using supramolecular gel method to construct xerogel sensing film material started late, there are several outstanding problems in the technical process of preparing xerogel sensing film
First, the luminescence efficiency of the xerogel sensing film is low, which affects its performance in terms of sensing performance
Second, there is still a lack of effective technical means to adjust the three-dimensional structure (such as the pore structure) of the xerogel sensing film to improve the sensing efficiency of the film.
However, the design strategy of the molecular structure of the xerogel sensing film with AIE properties still needs to be further developed.

Method used

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  • A kind of salicylaldehyde hydrazine AIE compound and its preparation method and the application of constructing high luminous efficiency xerogel sensing film
  • A kind of salicylaldehyde hydrazine AIE compound and its preparation method and the application of constructing high luminous efficiency xerogel sensing film
  • A kind of salicylaldehyde hydrazine AIE compound and its preparation method and the application of constructing high luminous efficiency xerogel sensing film

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Experimental program
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Effect test

Embodiment 1

[0085] Embodiment 1: Synthetic preparation of salicylaldehyde hydrazine class AIE compound (1)

[0086] 4,4'-Dihydroxybenzophenone (10.0 g, 46.7 mmol) and urotropine (19.6 g, 140.1 mmol) were added to 240 g (about 160 mL) of trifluoroacetic acid. Stir in a heating reaction device at 80 degrees Celsius for 15 hours, and the system is in a clear and transparent solution state during the reaction. Turn off the heating, and after the temperature drops to room temperature, add 80 mL of water and stir at room temperature for 3 hours to obtain a turbid system with a large amount of precipitates. Utilize the mode of suction filtration to separate the solid crude product, and then utilize the method for column chromatography (100-200 mesh silica gel column, sherwood oil / dichloromethane is used as developing agent with the ratio of 4:1) to purify the solid crude product, Obtained N', N'-((1E,1'E)-(carbonylbis(6-hydroxyl-3,1-phenylene))bis(formimide))bis(benzohydrazide) 21.8g( Yield ab...

Embodiment 2

[0089] Embodiment 2: Synthetic preparation of salicylaldehyde hydrazine class AIE compound (2)

[0090]The synthesis method of the salicylaldehyde hydrazine type AIE compound (2) is the same as the method for synthesizing the above salicylaldehyde hydrazine type AIE compound (1) (Example 1). The starting material benzohydrazide was replaced by p-methoxybenzohydrazide (2.9 g, 17.7 mmol). (yield: 92%) Elemental analysis: C, 65.88; H, 4.51; N, 9.81. Mass spectrometry: 566.01.

[0091]

Embodiment 3

[0092] Embodiment 3: Synthetic preparation of salicylaldehyde hydrazine class AIE compound (3)

[0093] The synthesis method of the salicylaldehyde hydrazine type AIE compound (3) is the same as the method for synthesizing the above salicylaldehyde hydrazine type AIE compound (1) (Example 1). The starting material benzohydrazide was replaced by p-ethoxybenzohydrazide (3.2 g, 17.7 mmol). (yield: 92%) Elemental analysis: C, 66.82; H, 4.94; N, 9.39. Mass spectrometry: 594.62.

[0094]

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Abstract

The invention discloses a salicylaldehyde hydrazine AIE compound, a preparation method thereof and the application of constructing a dry gel sensing film with high luminous efficiency. The method comprises: mixing bisphenol raw materials and urotropine to synthesize salicylaldehyde derivative intermediate products; adding benzoylhydrazone derivatives and glacial acetic acid to obtain salicylaldehyde hydrazine AIE compounds. The dry gel thin film with high luminous efficiency is prepared by supramolecular gel method. The compounds used to prepare high-luminous-efficiency xerogel sensing films have rich molecular design structures, simple synthesis methods, and high yields. The compound molecule has AIE fluorescence emission behavior, and the xerogel sensing film has high luminescence efficiency. The preparation method of the xerogel sensing film is simple, does not depend on large instruments, reduces industrial costs, and is conducive to the large-scale and cheap preparation of thin film sensing materials. Utilizing the self-shrinking behavior of the gel, the effective regulation of the pore structure of the xerogel sensing film and the significant enhancement of the fluorescence intensity can be realized.

Description

technical field [0001] The invention belongs to the technical field of supramolecular fluorescence detection, and specifically relates to a salicylaldehyde hydrazine-type AIE compound, a preparation method thereof, and the application of constructing a dry gel sensing film with high luminous efficiency. Background technique [0002] Thin-film sensors have the advantages of relatively stable structure, low diffusion resistance of the analyte, basically no pollution to the analyte system, easy deviceization, and reusability. play a very important role. With the increasing demand for anti-terrorism public safety (such as chemical dangerous goods detection, etc.), environmental quality monitoring (such as air humidity monitoring, gas concentration analysis, gas pollutant detection, etc.), biomedical diagnosis, food quality monitoring, etc., the international community is demanding The research of various high-performance thin film sensors has been paid more and more attention. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C251/86C07C249/16C09K11/06B01J13/00G01N21/64
CPCB01J13/0091C07C249/16C07C251/86C09K11/06C09K2211/1007G01N21/64
Inventor 唐本忠王志明马瑶李保玺张可心
Owner SOUTH CHINA UNIV OF TECH
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