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
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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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