Fluorescent probe for detecting 4-methylthiophenol and preparation method thereof
A technology of methyl thiophenol and fluorescent probe, which is applied in the field of fluorescent probe detection, can solve the problems of low specificity of fluorescent probe detection, and achieve the effects of easy acquisition, good membrane permeability and high sensitivity
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Embodiment 1
[0058] Add isophorone (1.38 g, 10 mmol) and malononitrile (0.72 g, 12 mmol) to 100 mL of ethanol, drop a few drops of glacial acetic acid, then add 100 μL of piperidine dropwise, and react at reflux at 70°C for 12 h . After the reaction was completed, the mixed solution was cooled to room temperature, poured into ice water, and kept overnight. The solution was filtered, washed, and recrystallized from n-heptane to obtain a pale yellow compound (II) as a solid.
[0059] In a nitrogen atmosphere, compound (II) (1.86 g, 10 mmol) and 4-hydroxy-3-methoxybenzaldehyde (1.59 g, 13 mmol) were dissolved in 15 mL of absolute ethanol, and then 100 μL of piperin Pyridine was heated to 70°C for 8 h under reflux. After the reaction was completed, the solution was evaporated in vacuo and purified by column chromatography (dichloromethane / ethyl acetate=6:1, V / V) to obtain compound (III) as a yellow solid.
[0060] Dissolve compound (III) (0.64 g, 2.0 mmol) in 10 mL N,N - Add 1-fluoro-2,4-...
Embodiment 2
[0066] Add isophorone (2.76 g, 20 mmol) and malononitrile (1.50 g, 25 mmol) to 100 mL of ethanol, drop a few drops of glacial acetic acid, then add 200 μL of piperidine dropwise, and react under reflux at 75°C for 12 h . After the reaction was completed, the mixed solution was cooled to room temperature, poured into ice water, and kept overnight. The solution was filtered, washed, and the crude product was purified by column chromatography (eluent dichloromethane) to obtain compound (II) as a light yellow solid.
[0067] In a nitrogen atmosphere, compound (II) (1.86 g, 10 mmol) and 4-hydroxy-3-methoxybenzaldehyde (1.83 g, 15 mmol) were dissolved in 20 mL of absolute ethanol, and then 100 μL of piperin Pyridine was heated to 70°C under reflux for 12 h. After the reaction was completed, the solution was evaporated in vacuo and purified by column chromatography (dichloromethane / ethyl acetate=6:1, V / V) to obtain compound (III) as a yellow solid.
[0068] Dissolve compound (III)...
Embodiment 3
[0070] Add isophorone (1.38 g, 10 mmol) and malononitrile (0.90 g, 15 mmol) to 100 mL of ethanol, add a few drops of glacial acetic acid, and then add 100 μL of piperidine dropwise, and react under reflux at 65°C for 12 h . After the reaction was completed, the mixed solution was cooled to room temperature, poured into ice water, and kept overnight. The solution was filtered, washed, and recrystallized from n-heptane to obtain a pale yellow compound (II) as a solid.
[0071] In a nitrogen atmosphere, compound (II) (1.67 g, 9 mmol) and 4-hydroxy-3-methoxybenzaldehyde (1.58 g, 13 mmol) were dissolved in 15 mL of absolute ethanol, and then 100 μL of piperidine was added dropwise , heated to 70°C for 8 h under reflux. After the reaction was completed, the solution was evaporated in vacuo and purified by column chromatography (dichloromethane / ethyl acetate=6:1, V / V) to obtain compound (III) as a yellow solid.
[0072] Dissolve compound (III) (0.64 g, 2.0 mmol) in 10 mL N,N - A...
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