Perylene diimide derivatives and its electrical impedance type differential detection pyridine derivative sensor and its preparation method and application

A technology of perylene diimide and derivatives, which is applied in the field of organic semiconductor materials, can solve the problems of few detection methods of gas-phase pyridine and its derivatives, complicated analytical instruments, difficult to carry, etc., and achieves good photostability and device preparation. Convenient and good photoelectric activity

Active Publication Date: 2022-03-29
SHAANXI SCI TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, current detection methods not only require complex analytical instruments, but these instruments are time-consuming and not portable
More importantly, the usual detection methods are often only aimed at the detection of pyridine and its derivatives in water, but there are few detection methods for gas phase pyridine and its derivatives.

Method used

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  • Perylene diimide derivatives and its electrical impedance type differential detection pyridine derivative sensor and its preparation method and application
  • Perylene diimide derivatives and its electrical impedance type differential detection pyridine derivative sensor and its preparation method and application
  • Perylene diimide derivatives and its electrical impedance type differential detection pyridine derivative sensor and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Example 1: Synthesis of PBI-1N and preparation of pyridine derivative sensor

[0049] (1) Synthesis of PBI-1N molecules:

[0050] N,N-Diisooctylamino-1-bromo-perylenediimide (2mmol), sulfonic acid (2-dicyclohexylphosphino-2',6'-diisopropoxy-1,1 '-biphenyl)(2-amino-1,1'-biphenyl-2-yl)palladium(II) (0.1mmol), 2-dicyclohexylphosphine-2',6'-diisopropoxy Add biphenyl (0.1mmol) and cesium carbonate (6mmol) into a 50mL round-bottomed flask, flush with nitrogen for more than 3 times, then add 40mL 1,4-dioxane and azetidine (2mmol), and then add Stir at 100° C. for 24 h under the protection of nitrogen. After the reaction, the reaction liquid is extracted with dichloromethane and filtered with diatomaceous earth. The filtrate is collected and spin-dried. Using silica gel as a chromatographic column and ethyl acetate / petroleum ether (1:6, volume ratio) as eluent, the obtained product was purified with a yield of 50%.

[0051] The structural formula is as follows:

[0052]

...

Embodiment 2

[0065] Example 2: Synthesis of PBI-2N and preparation of pyridine derivative sensor

[0066] (1) Synthesis of PBI-2N molecules:

[0067] N,N-Diisooctylamino-1-bromo-perylenediimide (2mmol), sulfonic acid (2-dicyclohexylphosphino-2',6'-diisopropoxy-1,1 '-biphenyl)(2-amino-1,1'-biphenyl-2-yl)palladium(II) (0.2mmol), 2-dicyclohexylphosphine-2',6'-diisopropoxy Add biphenyl (0.2mmol) and cesium carbonate (6mmol) into a 50mL round-bottomed flask, flush with nitrogen for more than 3 times, then add 40mL 1,4-dioxane and azetidine (4mmol), and then add Stir at 100° C. for 24 h under the protection of nitrogen. After the reaction, the reaction liquid is extracted with dichloromethane and filtered with diatomaceous earth. The filtrate is collected and spin-dried. Using silica gel as a chromatographic column and ethyl acetate / petroleum ether (1:6, volume ratio) as eluent, the obtained product was purified with a yield of 60%.

[0068] The structural formula is as follows:

[0069] ...

Embodiment 3

[0080] Embodiment 3: Measurement experiment of sensor external interference based on PBI-1N thin film.

[0081] In order to detect the influence of the gas sensor on the sensitivity of the sensor under external interference, the saturated vapor of air, water and organic solvents (ethyl acetate, toluene, acetonitrile and n-hexane) were respectively selected at the same temperature, and the response strength of the device was tested. The results like Figure 4 shown. from Figure 4 It can be seen that, for air interference, the PBI-1N film sensor of the present invention has almost no response, and for water vapor, there is almost no response intensity. At the same time, there was no response to the saturated vapor of the interfering substances of organic solvents (ethyl acetate, toluene, acetonitrile and n-hexane). It can be seen that the PBI-1N thin film sensor of the present invention has good resistance to interference from external air, water and organic solvents.

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Abstract

The invention discloses a perylene diimide derivative and an electrical impedance type differential detection pyridine derivative sensor based on the same, a preparation method and an application thereof, and belongs to the technical field of organic semiconductor materials. The electrical impedance sensor of the present invention includes interdigital electrodes and organic active layer materials, the organic active layer materials are perylene diimide derivatives PBI-1N and PBI-2N, which are loaded on the interdigital electrodes by solution spin coating technology, And its thickness is 50-100nm. The pyridine sensor of the present invention is convenient to prepare, easy to operate, and has obvious distinguishing and detecting effects on pyridine and its derivatives, and the minimum detection limit of pyridine sensing intensity can reach ppb level; the sensor has strong resistance to interferences such as organic solvents, water and air. good resistance. In addition, the sensor of pyridine and its derivatives of the present invention has high stability and fast response time.

Description

technical field [0001] The invention belongs to the technical field of organic semiconductor materials, and in particular relates to a perylene diimide derivative and an electrical impedance type discrimination detection pyridine derivative sensor based on the same, as well as a preparation method and application thereof. Background technique [0002] Pyridine is an organic colorless volatile liquid with an unpleasant smell, mainly refined or chemically synthesized from coal tar. Pyridine is an amphiphilic molecule with high solubility in water and non-polar solvents. At the same time, pyridine is also a toxic, carcinogenic and teratogenic compound, which has been listed as a priority pollution by the US Environmental Protection Agency (USEPA) The U.S. Environmental Protection Agency stipulates that the concentration of pyridine in the discharged wastewater should not exceed 5mg·l -1 level of supervision. In addition, pyridine and its derivatives have also been detected in...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/06G01N27/07
CPCC07D487/06G01N27/07
Inventor 刘全张强邵先钊王伟田光辉季晓晖
Owner SHAANXI SCI TECH UNIV
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