An organic circularly polarized luminescent material with both force-induced luminescence and aggregation-induced luminescence, and its preparation method and application
A technology for aggregation-induced luminescence and luminescent materials, which is applied in the field of organic circularly polarized luminescent materials and their preparation, can solve problems that have not been reported before, and achieve high yield, suitable for large-scale production, and simple synthesis methods and purification processes Effect
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Embodiment 1
[0077] Synthesis of target compound (I):
[0078] Under argon, 4-fluorophthalic anhydride (1.50 g, 9.04 mmol) and (R)-1,2,3,4-tetrahydro-1-naphthol (1.33 g, 9.04 mmol) were added into a three-necked flask, dissolve with 15 mL of N,N-dimethylformamide (DMF), and stir the reaction at 150° C. for 24 hours. After the reaction solution was cooled to room temperature, poured into 150 mL of water, extracted three times with dichloromethane, the organic layers were combined and dried with anhydrous sodium sulfate, filtered with suction, and the solvent was distilled off under reduced pressure by a rotary evaporator, and the obtained crude product was in a volume ratio of 1:2 mixed solution of dichloromethane and petroleum ether was used as the mobile phase for separation and purification by silica gel column chromatography. The obtained product was recrystallized with dichloromethane and methanol, filtered with suction, and dried in vacuo to obtain 1.22 g of yellow-green crystals [tar...
Embodiment 2
[0082] Synthesis of target compound (I):
[0083] Under argon, 4-fluorophthalic anhydride (1.50 g, 9.04 mmol) and (S)-1,2,3,4-tetrahydro-1-naphthol (1.50 g, 9.04 mmol) were added into a three-necked flask, dissolved in 15 mL of DMF, and stirred for 24 hours at 150°C. After the reaction solution was cooled to room temperature, it was poured into 150 mL of water, extracted three times with dichloromethane, the organic layers were combined and dried with anhydrous sodium sulfate, filtered with suction, and the solvent was distilled off under reduced pressure through a rotary evaporator, and the obtained crude product was in a volume ratio of 1:2 mixed solution of dichloromethane and petroleum ether was used as the mobile phase for separation and purification by silica gel column chromatography, the obtained product was recrystallized with dichloromethane and methanol, filtered with suction, and dried in vacuo to obtain 1.16 g of yellow-green crystals [target compound]. (I), S-3]...
Embodiment 3
[0087] Synthesis of target compound (II):
[0088] 1) Synthesis of compound 1:
[0089] Under argon, 4-bromophthalic anhydride (1.50 g, 6.64 mmol) and (R)-1,2,3,4-tetrahydro-1-naphthol (0.98 g, 6.64 mmol) were added into a three-necked flask, dissolved in 15 mL of DMF, and stirred for 24 hours at 150°C. After the reaction solution was cooled to room temperature, poured into 150 mL of water to separate out the solid, suction filtered, and the obtained crude product was separated and purified by silica gel column chromatography using a mixed solution of dichloromethane and petroleum ether with a volume ratio of 1:2 as the mobile phase, and dried in vacuo. Afterwards, 1.84 g of white powder (compound 1, R-ImNBr) was obtained, and the yield was about 78%. The reaction formula was as follows:
[0090]
[0091] 2) Synthesis of target compound (II):
[0092] Compound 1 (1.00g, 2.82mmol), carbazole compound (0.59g, 3.52mmol), anhydrous potassium phosphate (0.75g, 3.52mmol), 2-di...
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