4,10-Dioxo-5,9-diboronpyrene derivative, preparation method and application
A technology of pyrene derivatives and derivatives, which is applied in the field of functional materials based on 4,10-dioxo-5,9-diboronpyrene derivatives, can solve problems such as scarcity of materials, and achieve development-promoting, short excited state lifetimes Effect
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Embodiment 1
[0144] Embodiment 1: compound BO3 can be synthesized according to the following route:
[0145]
[0146] Add 2,6-dimethoxyphenylboronic acid (3.7143g, 20mmol, 98%, 1.0eq), palladium acetate (0.1123g, 0.5mmol, 0.025eq) and Solid S-Phos (0.5027g, 1.2mmol, 98%, 0.06 equiv). The nitrogen was replaced three times, and then 1,4-dioxane (60 mL), iodobenzene (4.5796 g, 22 mmol, 98%, 1.1 equivalents) and potassium carbonate (8.2920 g, 60 mmol, 3.0 equivalents) were added under nitrogen protection. aqueous solution (20 mL). Then place the three-neck flask in an oil bath at 105°C. After stirring for 12 hours, the reaction was complete as monitored by TLC. After cooling to room temperature, the organic phase was separated, and the aqueous phase was extracted with ethyl acetate (10 mL×2). All organic phases were combined, dried over anhydrous sodium sulfate, filtered, concentrated, and the resulting crude product was separated and purified by flash silica gel column chromatography (...
Embodiment 2
[0151] Embodiment 2: compound BO80 can be synthesized according to the following route:
[0152]
[0153]Add 2,6-dimethoxyphenylboronic acid (3.7143g, 20mmol, 98%, 1.0eq), 4-iodotoluene (4.8939g, 22mmol, 98%, 1.1 eq), palladium acetate (0.0898 g, 0.4 mmol, 0.02 eq) and ligand S-Phos (0.3351 g, 0.8 mmol, 98%, 0.04 eq). Nitrogen was evacuated three times, then an aqueous solution (20 mL) of 1,4-dioxane (60 mL) and potassium carbonate (8.2920 g, 60 mmol, 3.0 equiv) was added under nitrogen protection. Then place the three-neck flask in a 100°C oil bath. After stirring for 16 hours, the reaction was complete as monitored by TLC. After cooling to room temperature, the organic phase was separated, and the aqueous phase was extracted with ethyl acetate (10 mL×2). All organic phases were combined, dried over anhydrous sodium sulfate, filtered, concentrated, and the obtained crude product was separated and purified by flash silica gel column chromatography (eluent: petroleum ethe...
Embodiment 3
[0157] Embodiment 3: Compound BO312 can be synthesized according to the following route:
[0158]
[0159] Add 2,6-dimethoxyphenylboronic acid (4.0857g, 22mmol, 98%, 1.2 equivalents), 4-iodo-1,1'-biphenyl (5.7753g , 20mmol, 97%, 1.0eq), palladium acetate (0.0898g, 0.4mmol, 0.02eq) and ligand S-Phos (0.3351g, 0.8mmol, 98%, 0.04eq). Nitrogen was evacuated three times, then an aqueous solution (20 mL) of 1,4-dioxane (60 mL) and potassium carbonate (8.2920 g, 60 mmol, 3.0 equiv) was added under nitrogen protection. Then place the three-neck flask in a 100°C oil bath. After stirring for 17 hours, the reaction was complete as monitored by TLC. After cooling to room temperature, the organic phase was separated, and the aqueous phase was extracted with ethyl acetate (10 mL×2). All organic phases were combined, dried over anhydrous sodium sulfate, filtered, concentrated, and the obtained crude product was separated and purified by flash silica gel column chromatography (eluent: p...
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