Electron-rich fused ring aryl nitrone fluorescent probe as well as preparation and application thereof
A technology of condensed ring aryl nitrones and fluorescent probes, which is applied in the field of electron-rich condensed aryl nitrones fluorescent probes, and achieves the effects of strong identification, avoiding toxicity and pollution, and good water solubility.
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Embodiment 1
[0056] The preparation method of the fluorescent probe whose fused ring aryl group is substituted carbazole shown in formula Ⅰ-1, its synthetic route is as follows:
[0057]
[0058] The specific steps can be as follows:
[0059] 1) compound 4-oxindole (2mmol, 590mg) shown in formula B and AlCl 3 (1mmol, 14mg) was dissolved in 20mL acetic acid solution, then the compound represented by formula A (2.4mmol, 350mg) was added, and stirred at 40°C for 2h. After cooling, add 6 mL of saturated sodium bicarbonate solution to quench the reaction, extract three times with dichloromethane (6 mL), extract and recover the organic phase, and dry over anhydrous sodium sulfate. The crude product was separated and purified by silica gel column, the eluent was petroleum ether:ethyl acetate=40:1~30:1 (volume ratio), gradient elution, and a white solid substituted carbazole compound (Formula II-1) was obtained;
[0060] 2) Dissolve 37wt% formaldehyde solution of formula III (solute 1.92mmol,...
Embodiment 2
[0066] The condensed aryl group shown in formula Ⅰ-2 is the preparation method of the fluorescent probe of aminonaphthalene ring, and its synthetic route is as follows:
[0067]
[0068] The specific steps can be as follows:
[0069] 1) compound secondary amine (2mmol, R 1 , R 2 Both methyl) and acetic acid (4mmol, 229μL) were mixed to form a salt, then the compound represented by formula A (2mmol, 590mg) was added, and stirred at 120°C for 12h. After cooling, add 6 mL of saturated sodium bicarbonate solution to quench the reaction, extract three times with dichloromethane (6 mL), extract and recover the organic phase, and dry over anhydrous sodium sulfate. The crude product was separated and purified by silica gel column, the eluent was petroleum ether:ethyl acetate=30:1~20:1 (volume ratio), gradient elution, and white solid arylaminonaphthalene ring compound (Formula II-2) was obtained ;
[0070] 2) Dissolve 37wt% formaldehyde solution of formula (III) (solute 1.92mmo...
Embodiment 3
[0075] Embodiment 3: Fluorescent probe shown in formula I-1 measures carbon center free radical
[0076] 1) Prepare the fluorescent probe shown in formula I-1 with ethanol to 1×10 -4 g / L fluorescent probe indicator solution;
[0077]2) Dissolve azobisisobutyronitrile (AIBN) in tetrahydrofuran and prepare a concentration gradient of 1×10 -5 ~1×10 -3 g / L solution, heated at 70°C for 30 minutes.
[0078] 3) After the solution is cooled, in the azobisisobutyronitrile (AIBN) solution of different gradients, titrate the fluorescent probe indicator solution shown in the same amount of formula I, test the fluorescence intensity (that is, directly use the fluorescence spectrophotometer Measure the point value), draw the fluorescence titration curve (for example, you can set the test fluorescence titration curve in the fluorescence spectrophotometer, and the point value automatically regresses to generate the curve).
[0079] 4) By testing the fluorescence spectrum (such as figure ...
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