Electric impedance type biogenic amine sensor based on naphthalene-terminated terthienyl derivative and preparation method and application thereof
A technology of triple thiophene and derivatives, applied in the fields of material impedance, organic chemistry, etc., can solve the problems of complex preparation process of polymer materials, limit the development of sensor materials, and not easy to modify, so as to improve thermal stability and photostability, response No attenuation of strength and good stability
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Embodiment 1
[0047] Example 1: Synthesis of NA-3T and preparation of biogenic amine sensor
[0048] (1) Synthesis of NA-3T molecule:
[0049] Prepare the Grignard reagent of 1-substituted naphthalene with 2.11 mL (15.2 mmol) of 1-bromonaphthalene, 0.4 g (16.6 mmol) magnesium and a small amount of iodine in 80 mL THF, and then stir the prepared 1-naphthalene under nitrogen protection at low temperature. The Grignard reagent of substituted naphthalene was slowly added dropwise to a 100 mL THF solution of 2.58 g (6.9 mmol) of bromo-substituted terthiophene and 0.37 g (0.69 mmol) of dichloro-1,3-bis(diphenylphosphino)propane nickel. It was then heated to reflux for 15 hours and finally quenched by adding saturated ammonium chloride solution. Using silica gel as a chromatographic column and dichloromethane / n-hexane (1:6, volume ratio) as eluent, the obtained product was purified with a yield of 80%.
[0050] The structural formula is as follows:
[0051]
[0052] The corresponding physica...
Embodiment 2
[0063] Example 2: Synthesis of NA-3T-NA and preparation of biogenic amine sensor
[0064] (1) Synthesis of NA-3T-NA molecules:
[0065] 2.11mL (15.2mmol) of 1-bromonaphthalene, 0.4g (16.6mmol) magnesium and a small amount of iodine were prepared in 80mLTHF to prepare the Grignard reagent of 1-substituted naphthalene, and then the prepared 1-substituted naphthalene was stirred under nitrogen protection at low temperature. The Grignard reagent of naphthalene was slowly added dropwise to a 100 mL THF solution of 2.80 g (6.9 mmol) of dibromosubstituted terthiophene and 0.37 g (0.69 mmol) of dichloro-1,3-bis(diphenylphosphino)propane nickel. It was then heated to reflux for 15 hours and finally quenched by adding saturated ammonium chloride solution. Using silica gel as a chromatographic column and dichloromethane / n-hexane (1:6, volume ratio) as eluent, the obtained product was purified with a yield of 75%.
[0066] The structural formula is as follows:
[0067]
[0068] The ...
Embodiment 3
[0079] Embodiment 3: Measurement of sensor selectivity based on NA-3T film.
[0080] In order to test the selectivity of the gas sensor, dopamine, tyramine, histamine, tryptamine, trimethylamine, spermine, spermidine, cadaverine, putrescine, hexamethylenediamine, methanol, water, and chloroform were respectively selected at the same temperature , acetone, ether, acetonitrile and n-hexane saturated vapor, test the response strength of the device, the results are as follows image 3 shown. From image 3 It can be seen that, for the saturated vapor of spermine, spermidine, cadaverine, putrescine, hexamethylenediamine, the NA-3T film sensor of the present invention has almost no response, while for dopamine, tyramine, group For the saturated vapor of amine, tryptamine and trimethylamine, it has better response intensity. Also, there was no response to saturated vapors of methanol, water, chloroform, acetone, diethyl ether, acetonitrile, and n-hexane interferents. It can be see...
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