Cyclopentyl bithiophene organic small molecule photovoltaic material as well as preparation method and application thereof
A technology of cyclopentathiophene and benzothiadiazolylene cyclopentathiophene, which is applied in the field of organic small molecule photovoltaic materials, can solve the problems of difficult purification of products, batches that affect the efficiency of solar cells, and wide molecular weight distribution.
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Embodiment 1
[0044] Synthesis of Compound C
[0045]
[0046] Compound A (240 mg, 0.354 mmol) was dissolved in a mixed solution of 10 mL of ultra-dry toluene and 2 ml of ultra-dry N,N-dimethylformamide, and the reaction system was pumped and ventilated three times using a Schlenk double-row tube system. Tetrakis(triphenylphosphine)palladium (10 mg, 0.008 mmol) was then weighed and added to the reaction system, and the gas was ventilated three times, and the reaction system was sealed and refluxed at 110° C. for 24 hours in the dark. After the reaction was completed, an appropriate amount of saturated potassium fluoride solution was added to quench the reaction, and stirred for 15 minutes. Repeated extraction with deionized water and dichloromethane, saturated aqueous sodium chloride solution demulsification. The organic phase was purified by silica gel column chromatography with petroleum ether as eluent. Finally, a red viscous liquid was obtained, namely compound C (180 mg, yield 84....
Embodiment 2
[0049] Synthesis of Compound D
[0050]
[0051] At 0°C, add 0.2ml of ultra-dry N,N-dimethylformamide (189mg, 2.586mmol) to the dry reaction flask, stir and cool, then add 0.24ml of phosphorus oxychloride (396mg, 2.586mmol) dropwise, After the solution became white and viscous, it was transferred to room temperature to react for 1 hour. Measure 100mg (0.084mmol) of compound C and dissolve it in 11ml of 1,2-dichloroethane, drop it into the reaction bottle at 0°C under argon atmosphere, stir for half an hour, transfer to room temperature, and heat at 85°C for 12 hours. Cool the reaction system to room temperature, pour the reaction solution into a 100ml reaction bottle at 0°C, and slowly add saturated aqueous sodium carbonate solution dropwise at this temperature, transfer the reaction solution into a separatory funnel after neutralization, and use a deionized Water and dichloromethane were extracted several times, and the organic phase was dried by anhydrous magnesium sulfa...
Embodiment 3
[0054] Synthesis of compound 2FBCDT2R
[0055]
[0056] Weigh 100mg (0.080mmol) of compound D in a dry reaction flask, add 8 times the equivalent of 3-ethyl rhodanine (103mg, 0.64mmol), 16 times the equivalent of ammonium acetate (98.7mg, 1.28mmol), 12ml glacial acetic acid as solvent. The reaction system was pumped and ventilated three times using the Schlenk double-row tube system, and the reaction system was sealed and refluxed at 120° C. for 24 hours in the dark. After the reaction, cool to room temperature, transfer the reaction solution to a separatory funnel, extract with dichloromethane and water several times, break the emulsion with saturated sodium chloride solution, dry the organic phase with anhydrous magnesium sulfate, and then use silica gel column chromatography to separate and purify , the eluent is a mixed solution of petroleum ether and dichloromethane (4:1~2:1, v / v), and the solid obtained by column chromatography is precipitated with chloroform and met...
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