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Salicylaldehyde hydrazine AIE compound, preparation method thereof, and application to construction of high-luminous-efficiency xerogel sensing film

A high luminous efficiency, sensing thin film technology, 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, affecting sensing performance, etc. , to achieve the effects of large-scale and cheap preparation, reduction of industrial costs, and improvement of luminous intensity

Active Publication Date: 2020-11-03
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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  • Salicylaldehyde hydrazine AIE compound, preparation method thereof, and application to construction of high-luminous-efficiency xerogel sensing film
  • Salicylaldehyde hydrazine AIE compound, preparation method thereof, and application to construction of high-luminous-efficiency xerogel sensing film
  • Salicylaldehyde hydrazine AIE compound, preparation method thereof, and application to construction of high-luminous-efficiency xerogel sensing film

Examples

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 of the salicylaldehyde hydrazine AIE compound and application to construction of a high-luminous-efficiency xerogel sensing film. The method comprises the following steps: mixing a bisphenol raw material with urotropine to synthesize a salicylaldehyde derivative intermediate product; and adding a benzoyl hydrazone derivative and glacial acetic acid to obtain the salicylaldehyde hydrazine AIE compound. The xerogel film with high luminous efficiency is prepared by a supramolecular gel method. The compound forpreparing the xerogel sensing film with high luminous efficiency is rich in molecular design structure, simple in synthesis method and high in yield. The compound molecules have AIE fluorescence emission behaviors, and the xerogel sensing film is high in luminous efficiency. The preparation method of the xerogel sensing film is simple, is not depend on large instruments, reduces the industrial cost, and is beneficial to large-scale cheap preparation of the film sensing material. By utilizing the self-contraction behavior of the gel, the effective regulation and control of the pore channel structure of the dry gel sensing film and the obvious 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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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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