Compounds and their applications
A technology of compounds and complexes, applied in the field of chemistry, can solve the problems of incapability of real-time imaging of gene transfer process and intracellular localization, lack of fluorescence characteristics, low transfection efficiency, etc., to achieve controllable material composition, high transfection efficiency, and synthetic The effect of simple process
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Embodiment 1
[0042] The synthesis of embodiment 1 compound 2
[0043] Add 2,7-dibromofluorene (5.05g, 15.69mmol) into 1,6-dibromohexane (47.58g, 195mmol), stir and heat to 65°C. Then 30 mL of 50% potassium hydroxide solution (357 mmol) and tetrabutylammonium bromide (0.6 g, 1.86 mmol) were added, stirred and heated to 75° C. for 18 minutes. The reaction was stopped, cooled to room temperature, extracted twice with dichloromethane (2×30 mL), the organic phase was washed twice with 1 mol dilute hydrochloric acid and water (2×30 mL), and then dried with anhydrous magnesium sulfate for half an hour. After concentration under reduced pressure, 6.96 g of the product was obtained by column chromatography (silica gel; petroleum ether) with a yield of 68.6%.
[0044] 1 H-NMR (400MHz, CDCl 3 ): δ7.54(d, 2H), 7.45(t, 4H), 3.30(t, 4H), 1.93(m, 4H), 1.67(m, 4H), 1.20(m, 4H), 1.10(m, 4H), 0.60(m, 4H).
Embodiment 2
[0045] The synthesis of embodiment 2 compound 3
[0046] Potassium acetate (2.64 g, 26.8 mmol) was added to a solution of compound 1 (2.38 g, 3.57 mmol) and diboronic acid pinacol ester (2.72 g, 10.72 mmol) in dioxane (60 mL), and nitrogen gas was blown for half an hour, Add 210 μmol of PdCl 2 (dppf), the temperature was raised to 80°C, and nitrogen gas was blown for half an hour. The reaction temperature was maintained at 80° C., and the reaction was carried out under nitrogen atmosphere for 12 hours. Stop the reaction, cool to room temperature, add an appropriate amount of water, extract twice with dichloromethane (2×30mL), wash the organic phase with brine and water twice (2×30mL), and then dry half with anhydrous magnesium sulfate. Hour. After concentration under reduced pressure, column chromatography (silica gel; n-hexane:dichloromethane=2:1, v / v) separated the product to obtain 1.05 g, with a yield of 52%.
[0047] 1 H-NMR (400MHz, CDCl 3 ): δ7.82(d, 2H), 7.73(d, ...
Embodiment 3
[0048] The synthesis of embodiment 3 compound 5
[0049] 3-Bromothiophene (30 g, 0.18 mol) was dissolved in 250 mL of hexane, and the above solution was cooled to -40°C to -50°C. Then n-BuLi was added dropwise into the above solution and stirred for 10 min. Then, THF was added dropwise via syringe until white 3-lithium thiophene salt precipitated. Stirring was continued for 1 hour and the temperature was raised to -10°C. Dry tetrahydrofuran (5-10 mL) was added to the above solution, along with 1,6-dibromohexane (110 mL, 0.72 mol). After stirring at room temperature for 2 hours, the mixture was extracted with ether and washed 3 times with 200 mL of water. The organic layer solution was dried over anhydrous magnesium sulfate, filtered and concentrated.
[0050] 1 H NMR (ppm, CDCl 3 ):7.24(d, 1H), 6.92(d, 1H), 3.40(t, 2H), 2.64(t, 2H), 1.86(m, 2H), 1.65(m, 2H), 1.5(m, 2H) , 1.2(m, 2H).
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