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A kind of discene-perylene diimide derivative and its synthesis method and its sensing application to gas-phase volatile aromatic hydrocarbons

A technology of perylene diimide and synthesis method, which is applied in the field of small molecule fluorescence sensing thin film materials, can solve the problems of affecting the diffusion of analyte molecules, discount of thin film sensing performance, poor permeability of thin films, etc. The effect of aggregation-induced fluorescence quenching, fully reversible sensing process, and fast response and recovery times

Active Publication Date: 2020-08-04
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, it is easy to produce strong intermolecular π-π interactions, resulting in fluorescence quenching, which often limits its application, and at the same time, poor solubility is not conducive to its wide application.
The fluorescent sensing film obtained by using it also has poor film permeability, which affects the diffusion of analyte molecules in the film, resulting in a greatly reduced film sensing performance.

Method used

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  • A kind of discene-perylene diimide derivative and its synthesis method and its sensing application to gas-phase volatile aromatic hydrocarbons
  • A kind of discene-perylene diimide derivative and its synthesis method and its sensing application to gas-phase volatile aromatic hydrocarbons
  • A kind of discene-perylene diimide derivative and its synthesis method and its sensing application to gas-phase volatile aromatic hydrocarbons

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] Preparation of target fluorescent compound (p-iodoaniline is used in this example, alkyl chain n=16)

[0072] 1) Synthesis of compound 1a

[0073] Add 1.00g of perylenetetracarboxylic anhydride, 11.2g of p-iodoaniline, and 17g of imidazole into the flask in turn, and under an argon atmosphere, heat to 140°C under strong reflux and stir for 33 hours, then cool the reaction solution to room temperature naturally, add dichloromethane, and then The resulting suspension was filtered with suction, rinsed with methanol and chloroform in order to remove excess p-iodoaniline, and the obtained material was vacuum-dried to obtain brown-red compound 1a;

[0074] Its reaction equation is as follows:

[0075]

[0076] 2) Preparation of compound 2

[0077] Add 17.8g of anthracene, 5.4g of benzoquinone, and 75mL of mesitylene into a 200mL flask in sequence, reflux and stir for 24 hours, cool to room temperature, and filter. The obtained solid was added into 100 mL of hot xylene, ...

Embodiment 2

[0094] Preparation of target fluorescent compound (p-iodoaniline is used in this example, alkyl chain n=2)

[0095] 1) Synthesis of compound 1a

[0096]Add 1.00g of perylenetetracarboxylic anhydride, 11.2g of p-iodoaniline, and 17g of imidazole into the flask in turn, and under an argon atmosphere, heat to 140°C under strong reflux and stir for 33 hours, then cool the reaction solution to room temperature naturally, add dichloromethane, and then The resulting suspension was filtered with suction, rinsed with methanol and chloroform in order to remove excess p-iodoaniline, and the obtained material was vacuum-dried to obtain brown-red compound 1a;

[0097]

[0098] 2) Preparation of compound 2

[0099] Add 17.8g of anthracene, 5.4g of benzoquinone, and 75mL of mesitylene into a 200mL flask in sequence, reflux and stir for 24 hours, cool to room temperature, and filter. The obtained solid was added into 100 mL of hot xylene, stirred for a while and filtered while hot, and t...

Embodiment 3

[0115] Preparation of target fluorescent compound (p-iodoaniline is used in this example, alkyl chain n=5)

[0116] 1) Synthesis of compound 1a

[0117] Add 1.00g of perylenetetracarboxylic anhydride, 11.2g of p-iodoaniline, and 17g of imidazole into the flask in turn, and under an argon atmosphere, heat to 140°C under strong reflux and stir for 33 hours, then cool the reaction solution to room temperature naturally, add dichloromethane, and then The resulting suspension was filtered with suction, rinsed with methanol and chloroform in order to remove excess p-iodoaniline, and the obtained material was vacuum-dried to obtain brown-red compound 1a;

[0118] Its reaction equation is as follows:

[0119]

[0120] 2) Preparation of compound 2

[0121] Add 17.8g of anthracene, 5.4g of benzoquinone, and 75mL of mesitylene into a 200mL flask in sequence, reflux and stir for 24 hours, cool to room temperature, and filter. The obtained solid was added into 100 mL of hot xylene, s...

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Abstract

The invention discloses a ptycene-perylene diimide derivative, a synthesis method thereof and sensing application to gas-phase volatile aromatic hydrocarbon. The ptycene-perylene diimide derivative has a special non-planar structure, so that a prepared sensing film has large specific surface area and porosity, and is rich in molecular channels, and good diffusion of molecules of an object to be detected in the film can be ensured; and meanwhile, by utilizing a capillary condensation phenomenon and the sensitive effect of fluorescent molecules on a surrounding environment in a high-excitation state, high sensitivity and high selectivity response to BTEX gas are realized, the response time and the recovery time are short, and a new thought is provided for gas-phase sensing of volatile organic compounds lacking photoelectric activity and preparation of a fluorescent sensing film with excellent performance. The preparation method is simple and convenient to operate and mild in reaction condition, the photochemistry stability and thermodynamic stability of a prepared fluorescent compound are good, and the obtained fluorescent sensing film is high in sensitivity, good in selectivity andlong in service life, and is an excellent fluorescent sensing film.

Description

technical field [0001] The invention belongs to the technical field of small molecule fluorescent sensing thin film materials, and in particular relates to a discene-perylene diimide derivative, a synthesis method thereof and a sensing application to gas-phase volatile aromatic hydrocarbon BTEX. Background technique [0002] As the main representative of volatile organic compounds (VOCs) in the air, aromatic hydrocarbons pose a huge threat to human health and the environment. They can cause serious damage to the human central nervous system and cause abnormal development of blood cells. They have been proven to be serious carcinogens substance. Among them, BTEX (the abbreviation of benzene, toluene, ethylbenzene, o-xylene, m-xylene and p-xylene) is more volatile and more toxic, and it exists in almost all petroleum and petroleum products, and is often used as a marker At the same time, the serious carcinogenicity and teratogenicity of BTEX make it extremely important to mon...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/06C09K11/06G01N21/88G01N21/64
CPCC07D471/06C09K11/06C09K2211/1007C09K2211/1011C09K2211/1029G01N21/6428G01N21/643G01N21/8851G01N2021/6432
Inventor 房喻王朝龙郭茸文瑞娟
Owner SHAANXI NORMAL UNIV
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