Conjugated polymer based on heteroaryl-2,8-S,S-dioxyl dibenzothiophene unit and preparation method and application thereof
A technology of dioxydibenzothiophene and conjugated polymers, applied in the field of conjugated polymers and their preparation, to achieve the effect of enriching optical and electrical properties
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Embodiment 1
[0063] Methyl 1-bromo-2-quinoxalinecarboxylate
[0064] 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 The results of CNMR, MS and elemental analysis showed that the obtained compound was the target product. The chemical reaction equation is as follows:
[0065]
Embodiment 2
[0067] Preparation of 2,8-Dibromothiofluorene
[0068] Under an argon atmosphere, add thiofluorene (20g, 108.54mmol) into a 250ml two-necked bottle, then add 100ml of chloroform to dissolve completely, add iodine (550.99mg, 2.17mmol), drop by drop under the condition of avoiding light Add liquid bromine (38.16g, 238.80mmol), the reaction solution was stirred under ice bath for 2 hours, then stirred at room temperature for 2 hours, added saturated sodium bisulfite to quench the liquid bromine, the reaction mixture was poured into water, washed with acetic acid Extracted with ethyl ester, the organic layer was washed completely with brine, and dried over anhydrous magnesium sulfate. After the solution was concentrated, a crude white solid was obtained, which was then recrystallized from chloroform with a yield of 85%. 1 HNMR, 13 The results of CNMR, MS and elemental analysis showed that the obtained compound was the target product. The chemical reaction equation is as follows...
Embodiment 3
[0071] 2,8-diborate thiofluorene
[0072] Under an argon atmosphere, 2,8-dibromothiofluorene (10 g, 29.24 mmol) was dissolved in 180 mL of refined tetrahydrofuran (THF), and 1.6 mol L-1 of n-butyllithium was gradually added dropwise at -78 °C 28mL, react for 2 hours, then quickly add 25mL of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborane, and continue to react for 1 hour at -78°C , slowly warming up to room temperature and reacting for 24 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 light yellow viscous crude product was obtained, which was purified by silica gel column chromatography (petroleum ether / ethyl acetate=20 / 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, the product rate of 70%. 1 H NMR and GC-MASS tests showed that it was t...
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