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Preparation method of dicationic carbazole fluorescent probe
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A dual-cation, fluorescent probe technology, applied in chemical instruments and methods, luminescent materials, etc., can solve the problems of high energy consumption and high cost, and achieve the effects of low cost, cheap and easy-to-obtain solvent, and simple operation.
Active Publication Date: 2017-03-01
TIANJIN CHENGJIAN UNIV
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[0004] The purpose of the present invention is to provide a method for preparing a dicationic carbazole fluorescent probe that can overcome the above-mentioned shortcomings of the prior art, and solve the problems of high energy consumption and high cost caused by column chromatography or expensive catalysts in the prior art
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Embodiment 1
[0020] Taking the preparation of 3,6-bis[2-(1′,3′,3′-trimethyl-benzoindole-2′-hexanoyl]-9-ethyl-carbazole bromide as an example
[0021] Add 0.53g of N-ethyl-3,6-dialdehyde carbazole and 1.61g of 1,3,3-trimethyl-2-hexanoyl-benzoindole bromide into a 100ml reaction flask , and then add 50ml of ethanol, 2.5ml of water, 0.3g of Zn(NO 3 ) 2 ·6H 2 O and 0.22g of Zn(CH 3 COO) 2 2H 2 O, the addition is complete, the temperature is 20-25 ° C for 12 hours, TLC monitoring, the raw material disappears, filter, the filter cake is transferred to a 100ml reaction bottle, add 2.5ml of N,N-dimethylformamide, 45ml of ethanol and 2.5 ml of water and stirred at room temperature for 2 hours. Suction filter, rinse with a little ethanol, TLC test shows a single spot. 1.47 g of product was obtained, yield 72%. The content is greater than 98.5%.
Embodiment 2
[0023] Taking the preparation of 3,6-bis[2-(1′,3′,3′-trimethyl-benzoindole-2′-propionyl]-9-hexyl-carbazole bromide as an example
[0024] Add 0.33g of N-hexyl-3,6-dialdehyde carbazole and 0.76g of 1,3,3-trimethyl-2-propionyl-benzoindole bromide in a 50ml reaction flask, Then add 25ml of methanol, 2.5ml of water, 0.11g of Zn(CH 3 COO) 2 2H 2 O, the addition is complete, the temperature is 20-25 ° C for 24 hours, TLC monitoring, the raw material disappears, filter, the filter cake is transferred to a 50ml reaction bottle, add 1.2ml of N,N-dimethylformamide, 22.5ml of ethanol and 1.2ml of water, stirred at room temperature for 2 hours. Suction filter, rinse with a little ethanol, TLC test shows a single spot. 0.71 g of product was obtained, yield 69%. The content is greater than 97.0%.
Embodiment 3
[0026] Taking the preparation of 3,6-bis[2-(1′,3′,3′-trimethyl-benzoindole-2′-methyl]-9-decyl-carbazole iodine salt as an example
[0027] Add 0.40 g of N-decyl-3,6-dialdehyde carbazole and 0.70 g of 1,3,3-trimethyl-2-methyl-benzoindole iodide in a 50 ml reaction flask, Then add 10ml ethanol, 10ml n-propanol, 1.6ml water, 0.07g ZnCl 2 , 0.22g of Zn(CH 3 COO) 2 2H 2 O, the addition is complete, the temperature is 20-25 ° C for 18 hours, TLC monitoring, the raw material disappears, filter, the filter cake is transferred to a 50ml reaction bottle, add 1.2ml of N,N-dimethylformamide, 22.5ml of ethanol and 1.2ml of water, stirred at room temperature for 2 hours. Suction filter, rinse with a little ethanol, TLC test shows a single spot. 0.74 g of product was obtained, yield 72%. The content is greater than 98.0%.
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Abstract
The invention provides a preparation method of a double-cationic carbazole fluorescent probe. The method comprises the following steps of adding 1mmol of N-alkyl-3,6-bi-aldehyde carbazole, 2-3mmol of benzo-indole salt, 20-50ml of mixed solvent and an inorganic salt catalyst sequentially into a reaction flask under the condition of magnetic stirring; reacting for 12-24h at 20-25 DEG C; extracting and filtering reaction liquid obtained after the reaction to obtain a crude product; and stirring and washing the crude product for 1-3 times by a washing solvent, then extracting and filtering again, and drying, so as to obtain the double-cationic carbazole compound. With a mixture of saturated fatty alcohol and water as a solvent, the solvent is cheap and easily available, the cost of the catalyst is low, the preparation method is easy to operate, the conversation rate is high, the column chromatography separation and expensive palladium acetate catalyst are not required, and the environment pollution is reduced. Through high-efficiency liquid phase detection, the optimal content of the product obtained by the preparation method of the double-cationic carbazole fluorescent probe is greater than 96%.
Description
technical field [0001] The invention relates to a preparation method of a dicationic carbazole fluorescent probe, in particular to a preparation method of a bisbenzindole cationic carbazole fluorescent probe. Background technique [0002] It is found that the double-cation carbazole salt has a large two-photon absorption interface, which has a wide range of potential applications. However, there is no simple, efficient and environmentally friendly method in the synthesis method. The Journal of Advanced Chemistry, 2010, 31, 1860-1863 reported a method for preparing a dicationic carbazole fluorescent probe, which was prepared by HECK reaction followed by salt formation. Requires the use of expensive catalysts and requires column chromatography with low overall yields. [0003] In New J.Chem., 2007, 31, 63-68, piperidine is used as a catalyst for the reaction, which has high energy consumption and low yield. Contents of the invention [0004] The purpose of the present inv...
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