Symmetric bifluorenylidene derivative having characteristic of multi-photon absorption, and synthesis method and application thereof
A technology of multiphoton absorption and synthesis method, which is applied in the field of symmetric bisfluorene derivatives and their synthesis, can solve the problems that excited state absorption cannot be ruled out, and achieve the effects of reasonable design, high stability, and large multiphoton absorption cross section
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Embodiment 1
[0033] Synthesis steps of 2,7,2',7'-tetrakis(4-methoxystyrene)-9,9'-bisfluorene:
[0034] (1) Add 15mmol (5.227g) dibromofluorenone to 300ml glacial acetic acid, heat to reflux, add 60mmol (3.90g) zinc powder, continue to heat and reflux for 20min, filter the reaction solution on diatomaceous earth, add Precipitate with water equal to the volume of the filtrate, and recrystallize and purify the obtained crude product with n-hexane to obtain solid 2,7-dibromo-9-hydroxyfluorene with a yield of 70%; 1 H-NMR (400MHz, CDCl 3 ): δppm 7.76 (s, 2H), 7.53 (dd, 2H, J 1 =1.2Hz,J 2 =1.6Hz), 7.48(d, 2H, 8Hz), 5.54(d, 1H, J=9.6), 1.93(d, 1H, J=10);
[0035] (2) Take 8mmol (2.768g) of 2,7-dibromo-9-hydroxyfluorene and add 80mmol (7.519ml) of PBr 3 , the mixture was heated to 150°C for 40 minutes, cooled to room temperature, poured into water 50 times the volume of the reaction solution, and added solid NaHCO 3 Adjust the pH value until neutral, then extract with dichloromethane, concent...
Embodiment 2
[0041] The synthesis method of 2,7,2',7'-tetrakis(4-methoxystyrene)-9,9'-bisfluorene is the same as in Example 1, the difference lies in the ratio of raw materials and the reaction in each step condition:
[0042] (1) 15mmol of 2,7-dibromofluorenone, 15mmol of zinc powder, 150ml of glacial acetic acid, react for 25min; when precipitating, the amount of water is 2 times the volume of the filtrate;
[0043] (2) 2,7-dibromo-9-hydroxyfluorene 8mmol, PBr 3 40mmol, react at 100°C for 20min; when adjusting the pH value, the amount of water is 20 times the volume of the reaction solution;
[0044] (3) 2.5mmol of 2,7,9-tribromofluorene, 2.5mmol of diazabicyclo, 200ml of acetonitrile, react at 55°C for 2.5h; wash with hot acetonitrile at 50°C;
[0045] (4) 2,7,2',7'-tetrabromo-9,9'-bisfluorene 0.493mmol, 4-methoxystyrene 2mmol, palladium acetate 0.02mmol, potassium carbonate 1mmol, tetrabutyl bromide Ammonium 0.25mmol, N,N-dimethylformamide 50ml, check reaction at 80°C for 7 days; t...
Embodiment 3
[0047] The synthesis method of 2,7,2',7'-tetrakis(4-methoxystyrene)-9,9'-bisfluorene is the same as in Example 1, the difference lies in the ratio of raw materials and the reaction in each step condition:
[0048] (1) 15mmol of 2,7-dibromofluorenone, 45mmol of zinc powder, 750ml of glacial acetic acid, react for 30min; when precipitating, the amount of water is 5 times the volume of the filtrate;
[0049] (2) 2,7-dibromo-9-hydroxyfluorene 8mmol, PBr 3 800mmol, react at 155°C for 120min; when adjusting the pH value, the amount of water is 200 times the volume of the reaction solution;
[0050] (3) 2.5mmol of 2,7,9-tribromofluorene, 5mmol of diazabicyclo, 300ml of acetonitrile, react at 65°C for 3h; rinse with hot acetonitrile at 70°C;
[0051] (4) 2,7,2',7'-tetrabromo-9,9'-bisfluorene 0.493mmol, 4-methoxystyrene 5mmol, palladium acetate 0.1mmol, potassium carbonate 10mmol, tetrabutyl bromide Ammonium 2.5mmol, N,N-dimethylformamide 250ml, check reaction at 150°C for 1 day; d...
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