Synthesis method of A-D-A configuration organic conjugated small molecules
A synthesis method and technology of small molecules, applied in the fields of silicon organic compounds, organic chemistry, chemical instruments and methods, etc., can solve the problems of complex process and low yield, and achieve the effect of improving yield, reaction activity and yield.
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Embodiment 1
[0033] (1) Preparation of compound shown in formula (I):
[0034] The 250 mL two-neck round bottom flask was vented with argon, and 2-formylthiophene (5.6 g, 50 mmol) and 100 mL of anhydrous tetrahydrofuran were added. Put the system into a low-temperature tank to lower the system to -18°C. Then titanium tetrachloride (6.5 mL) was added dropwise into the system and stirred at this temperature for 0.5 h. Add 200-300-mesh zinc powder (7.8g) into the reaction system, continue to stir for 0.5h, take it out, gradually return to normal temperature, then heat to 85°C and reflux for 3.5h.
[0035]Post-processing: add 100mL ice water to the reaction system to quench, pour the reaction solution into a separatory funnel, extract with dichloromethane, remove the lower organic phase, and extract the aqueous phase three times, then use anhydrous MgSO 4 Drying, filtration to remove insoluble solids after drying is complete, evaporation to remove the solvent to obtain a crude product, which...
Embodiment 2
[0054] Step (1) to step (3) are the same as step (1) to step (3) in Example 1.
[0055] (4) Preparation of compound shown in formula (IV):
[0056] Put a 100mL double-neck round bottom flask with a spherical condenser, vacuumize the double-row tube, and change the argon several times to exhaust the air in the bottle, and protect it with argon, and add tetrakistriphenylphosphopalladium to the bottle (250mg, 0.242mmol), 4,7-dibromobenzothiadiazole (0.65g, 2.42mmol), vacuumize and change the argon several times, and finally, under the protection of argon, add the compound III prepared in step (3) (1.14g, 2.22mmol), 20mL of anhydrous toluene, 20mL of anhydrous N,N-dimethylformamide (DMF), passed through condensed water, and refluxed at 120°C for 24h.
[0057] Post-processing: stop heating, add 20mL of dilute hydrochloric acid to quench the reaction system after cooling. Pour the reaction solution into a separatory funnel, extract with dichloromethane, remove the lower organic ph...
Embodiment 3
[0060] Steps (1) to (4) are the same as steps (1) to (4) in Example 1.
[0061] (5) Preparation of compound S1:
[0062] Put a 50mL double-neck round bottom flask with a spherical condenser, vacuumize the double-row tube and replace the air with argon, and cycle like this three times to do anhydrous and oxygen-free treatment. Add 2.5 equivalents of compound IV (169 mg, 0.328 mmol) prepared in step (4) and tetrakistriphenylphosphopalladium (37.9 mg, 0.0328 mmol) into the bottle. Then evacuate the double-row tube and fill it with argon, do this three times, exhaust the air, then add benzodithiophene R1 (118mg, 0.131mmol) with a thiophene side chain substituted by bistin, 30mL of anhydrous toluene, and condense Water, heated to 120°C, refluxed for 48h.
[0063] Post-processing: stop heating, wait for it to cool to room temperature, pour the reaction into a separatory funnel, extract with dichloromethane, remove the lower organic phase, extract the aqueous phase with dichloromet...
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