Oligomeric phenylene ethynylene (OPE) compounds as well as preparation method and application thereof
A technology of oligophenylene vinylene compounds, which is applied in the field of oligopolyphenylene vinylene compounds and their preparation, can solve the problems of strong cytotoxicity, etc., and achieve the effects of increasing water solubility, increasing medicinal value, and simple synthesis route
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Embodiment 1
[0032] Example 1 . Preparation of Compound (I)
[0033] 1 g (1.98 mmol) of OPE-1 was dissolved in 10 mL of anhydrous dichloromethane, and 396 mg (3.96 mmol) of diisopropylamine was added to obtain a colorless solution. 173 mg (0.99 mmol) e, 21 mg (0.03 mmol) (triphenylphosphine) palladium chloride, and 12 mg (0.06 mmol) cuprous iodide were added sequentially. After 7 hours, add 50 mL of dichloromethane to dilute the reaction system, add 20 mL of saturated ammonium chloride solution for washing, 20 mL of pure water and 20 mL of saturated sodium chloride, collect the organic phase, and wash with an appropriate amount of Dry magnesium sulfate with water for 30 minutes, remove magnesium sulfate by filtration, collect the organic phase, and remove the organic solvent by rotary evaporation under reduced pressure to obtain a light red solid. The solid was passed through a silica gel column to obtain a white solid (dichloromethane:methanol=10:1), yield: 75%. 1 H NMR (600 MHz, DMSO-d ...
Embodiment 2
[0034] Example 2 . Preparation of compound (I)
[0035] 1 g (1.98 mmol) of OPE-1 was dissolved in 10 mL of anhydrous dichloromethane, and 401 mg (3.96 mmol) of triethylamine was added to obtain a colorless solution. 173 mg (0.99 mmol) e, 21 mg (0.03 mmol) bis(triphenylphosphine) palladium chloride, and 12 mg (0.06 mmol) cuprous iodide were added sequentially. After 7 hours, add 50 mL of dichloromethane to dilute the reaction system, add 20 mL of saturated ammonium chloride solution for washing, 20 mL of pure water and 20 mL of saturated sodium chloride, collect the organic phase, and wash with an appropriate amount of Dry magnesium sulfate with water for 30 minutes, remove magnesium sulfate by filtration, collect the organic phase, and remove the organic solvent by rotary evaporation under reduced pressure to obtain a light red solid. The solid was passed through a silica gel column to obtain a white solid (dichloromethane:methanol=10:1), yield: 62%. 1 H NMR (600 MHz, DMSO-...
Embodiment 3
[0036] Example 3 . Preparation of compound (I)
[0037] 1 g (1.98 mmol) of OPE-1 was dissolved in 10 mL of anhydrous dichloromethane, and 396 mg (3.96 mmol) of diisopropylamine was added to obtain a colorless solution. Add 173 mg (0.99 mmol) e, 42 mg (0.06 mmol) (triphenylphosphine) palladium chloride, and 24 mg (0.12 mmol) cuprous iodide in sequence. After 7 hours, add 50 mL of dichloromethane to dilute the reaction system, add 20 mL of saturated ammonium chloride solution for washing, 20 mL of pure water and 20 mL of saturated sodium chloride, collect the organic phase, and wash with an appropriate amount of Dry magnesium sulfate with water for 30 minutes, remove magnesium sulfate by filtration, collect the organic phase, and remove the organic solvent by rotary evaporation under reduced pressure to obtain a light red solid. The solid was passed through a silica gel column to obtain a white solid (dichloromethane:methanol=10:1), yield: 81%. 1 H NMR (600 MHz, DMSO-d 6 ). ...
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