Conjugated polymers based on diaromatic heterocyclic-3,7-S,S-dioxodibenzothiophene units as well as preparation method and application of conjugated polymers
A kind of technology of dioxydibenzothiophene and conjugated polymer, which is applied in the field of conjugated polymer and its preparation
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Embodiment 1
[0062] Methyl 1-bromo-2-quinoxalinecarboxylate
[0063] Under an argon atmosphere, add 1-bromo-2-quinoxalinecarboxylic acid (10g, 37.83mmol) into a two-necked flask, then add 100mL of methanol, then add concentrated sulfuric acid (39.06mg, 398.29umol) dropwise, and heat to 110 °C, reacted for 18h. The reaction mixture was poured into water, extracted with ethyl acetate, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. After the solution was concentrated, a white solid crude product was obtained, which was purified by silica gel column chromatography (petroleum ether / dichloromethane=3 / 1, v / v was selected as the eluent), and the product was placed in the refrigerator for a long time to obtain a white solid with a yield of 85%. . 1 H NMR, 13 CNMR, MS and elemental analysis results show that the obtained compound is the target product, and its chemical reaction equation is as follows:
[0064]
Embodiment 2
[0066] Methyl 1-boronate-2-quinoxalinecarboxylate
[0067] Under argon atmosphere, the compound 1-bromo-2-quinoxalinecarboxylic acid methyl ester (10g, 37.72mmol) was dissolved in anhydrous tetrahydrofuran (THF), stirred at -78°C for 20 minutes, then added n-butyl Lithium (21.05g, 113.16mmol), stirred at -78°C for 2 hours, then added isopropoxy pinacol ester (9.66g, 150.88mmol), stirred at -78°C for 1 hour, and reacted at room temperature for 16 hours . The reaction mixture was poured into water, extracted with ethyl acetate, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. After the solution was concentrated, a white solid crude product was obtained, which was purified by silica gel column chromatography (petroleum ether / dichloromethane=2 / 1, v / v was selected as the eluent), and the product was placed in the refrigerator for a long time to obtain a white solid with a yield of 75%. . 1 H NMR, 13 CNMR, MS and elemental analysis results ...
Embodiment 3
[0070] Preparation of 3,7-dibromo-S,S-thiofluorene dioxide
[0071] (1) In a 150 mL round bottom flask, 5 g of biphenyl was dissolved in 80 mL of dichloromethane, 11.8 g of bromosuccinimide was added at room temperature, and then reacted at room temperature for 48 hours. After the reaction, the reactant was poured into water, extracted with dichloromethane, and washed with water. Dry over anhydrous magnesium sulfate, evaporate the solvent, and recrystallize from petroleum ether. 5.65 g of white solid was obtained, yield 75%.
[0072] (2) In a 150mL three-neck flask, add 20g of 4,4'-dibromobiphenyl, dissolve it in 50mL of chloroform, add 11.4mL of chlorosulfonic acid dropwise, keep the reaction system below 50°C, and react for 3 hours. After the reaction, the reactant was poured into 500mL of crushed ice, and the ice was melted with Na 2 CO 3 The solution was adjusted to be neutral, and the insoluble matter was filtered out, washed with water and dried, and then recrystalli...
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