Aggregation-induced luminescent material based on thieno[3,4-b]thiophene, its preparation method and application
An aggregation-induced luminescence and 4-b technology, which is applied in the field of aggregation-induced luminescence materials and preparations based on thieno[3,4-b]thiophene, can solve the problems of low absorption rate, decrease in fluorescence brightness, and destruction of conjugation, etc. Achieve the effects of simple reaction operation, small background fluorescence interference, and simple structure
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Embodiment 1
[0034] An aggregation-induced luminescent material based on thieno[3,4-b]thiophene, which uses triphenylamine and thieno[3,4-b]thiophene as core units, and its structural formula is:
[0035]
[0036] A method for preparing the above-mentioned aggregation-induced luminescent material based on thieno[3,4-b]thiophene, comprising the following steps:
[0037] Step 1, 4-methoxy-N-(4-methoxybenzene)-N-(4-(4,4,5,5,-tetramethyl-1,3,2-dioxaborin Fyl)phenyl)aniline (compound 1) (240mg, 0.55mmol) and 4-bromo-6-formylthieno[3,4-b]thiophene-2-ethyl carboxylate (compound 2) (150mg, 0.47mmol) was dissolved in 10mL of dry 1,4-dioxane, and Cs was added successively under the condition of nitrogen protection 2 CO 3 (456mg, 1.39mmol), bis(triphenylphosphine) palladium dichloride (20mg, 0.025mmol), heated to reflux at 90°C for 15h, after the reaction was completed, the reaction was cooled to room temperature. Quench the reaction with 2mol / L potassium fluoride solution of 3mL, extract with ...
Embodiment 2
[0042] A method for preparing the above-mentioned aggregation-induced luminescent material based on thieno[3,4-b]thiophene, comprising the following steps:
[0043] Step 1, 4-methoxy-N-(4-methoxybenzene)-N-(4-(4,4,5,5,-tetramethyl-1,3,2-dioxaborin Fyl)phenyl)aniline (compound 1) (240mg, 0.55mmol) and 4-bromo-6-formylthieno[3,4-b]thiophene-2-ethyl carboxylate (compound 2) (150mg, 0.47mmol) was dissolved in 10mL of dry 1,4-dioxane, and Cs was added successively under the condition of nitrogen protection 2 CO 3 (308.37mg, 0.94mmol), bis(triphenylphosphine)palladium dichloride (3.3mg, 0.004mmol), heated under reflux at 100°C for 18h, after the reaction was completed, the reaction was cooled to room temperature. Quench the reaction with 2mol / L potassium fluoride solution of 3mL, extract with dichloromethane and water after the solvent is removed, collect the organic phase and dry with anhydrous sodium sulfate, remove the organic solvent under reduced pressure, the crude product c...
Embodiment 3
[0048] A method for preparing the above-mentioned aggregation-induced luminescent material based on thieno[3,4-b]thiophene, comprising the following steps:
[0049] Step 1, 4-methoxy-N-(4-methoxybenzene)-N-(4-(4,4,5,5,-tetramethyl-1,3,2-dioxaborin Fyl)phenyl)aniline (compound 1) (240mg, 0.55mmol) and 4-bromo-6-formylthieno[3,4-b]thiophene-2-ethyl carboxylate (compound 2) (150mg, 0.47mmol) was dissolved in 10mL of dry 1,4-dioxane, and Cs was added successively under the condition of nitrogen protection 2 CO 3 (1541.87mg, 4.7mmol), bis(triphenylphosphine) palladium dichloride (33mg, 0.047mmol), heated to reflux at 95°C for 16h, after the reaction was completed, the reaction was cooled to room temperature. Quench the reaction with 2mol / L potassium fluoride solution of 3mL, extract with dichloromethane and water after the solvent is removed, collect the organic phase and dry with anhydrous sodium sulfate, remove the organic solvent under reduced pressure, the crude product colum...
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