Monodisperse polymer with main chain containing fluorene-butadiyne structure as well as preparation method and application of monodisperse polymer
A technology of polymers and diacetylene, applied in the field of monodisperse polymers and their preparation, can solve the problems of unsuitable for large-scale preparation of polymers, long time-consuming, many steps, etc., and achieve the convenience of industrial production, high efficiency, and reaction operation easy effect
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Embodiment 1
[0083] Example 1: Synthesis of fluorene donor
[0084] Under an atmosphere of argon protection, 2-bromo-7-iodofluorene (1.0 g, 1 eq.) was added to a 50 mL three-necked flask, dissolved in 10 mL of anhydrous tetrahydrofuran and 8 mL of diisopropylamine, and placed in 40 o In the C oil bath, stir with argon for 20 min. Add bistriphenylphosphine palladium dichloride (0.151 g, 0.08 eq.), cuprous iodide (0.041 g, 0.08 eq.) triphenylphosphine (0.057 g, 0.08 eq.) in turn to the mixture, and stir 20 min. Finally, trimethylsilylacetylene (570 μL, 1.5 eq.) was added and reacted for 6 h. After the reaction was completed, the reaction solution was cooled to room temperature, and the insoluble matter was removed by filtration. After the filtrate was concentrated by rotary evaporation, 50 mL of ethyl acetate was added to dissolve it, and washed three times with a large amount of water. The organic phase was collected, dried over anhydrous sodium sulfate, rotary evaporated, and purified ...
Embodiment 2
[0086] Example 2: Synthesis of fluorene-butadiyne monomer.
[0087] 1. Synthesis of asymmetric molecules with a bromine atom at one end and an alkyne hydrogen at the other end
[0088] Add compound (III) (1 g, 1 eq.) into a 100 mL single-necked round bottom flask, dissolve it in 40 mL dimethyl sulfoxide, and stir at room temperature for 10 min. After that, 50% potassium hydroxide aqueous solution was added to the reaction liquid, and stirred for 10 min. Measure 1.2 mL of 1-bromooctane in a constant pressure dropping funnel, and slowly drop it into the above solution, react at room temperature for 5 h, and purify by column chromatography (developing agent is pure petroleum ether), to obtain 0.7 g of light yellow liquid.
[0089]
[0090] 2. Synthesis of fluorene-butadiyne molecule with bromine atom at the end
[0091] Weigh compound (IV) (2 g, 1 eq.), cuprous chloride (210 mg, 0.5 eq.), add 10 mL chloroform to dissolve, then add 300 μL tetramethylethylenediamine, place at ...
Embodiment 3
[0100] Embodiment three: monodisperse polymer D -Synthesis and characterization of oFDAs
[0101] bi -FDA (1 g, 1.14 mmol, 1 eq.) was dissolved in 18 mL of N,N-dimethylformamide and stirred in an oil bath at 30°C. Then cuprous chloride (0.035 g, 0.34 mmol, 0.3 eq.) and N,N,N',N'-tetramethylethylenediamine (55 μL, 0.34 mmol, 0.3 eq.) were added to the above solution , and stirred for 1.5 h under air. Under normal stirring, the polymer solution was added dropwise into 50 mL of anhydrous methanol to obtain a polymer precipitate; after standing for 2 h, it was separated with a centrifuge (15000 r / min, 10 min), and conventionally dried to obtain a polymer (with comparison with performance testing), by matrix-assisted laser desorption ionization mass spectrometry (MALDI-TOF, figure 2 a) and gel permeation chromatography (GPC, figure 2 b) analysis, which can determine the exact molecular weight and number average molecular weight of each component in the resulting polymer ( ...
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