Formaldehyde fluorescent probe as well as preparation method and application thereof
A fluorescent probe, formaldehyde technology, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve problems such as the destructiveness of the detection substance, and achieve the effects of simple detection, simple synthesis and high yield
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Embodiment 1
[0044] Synthesis of compound 2:
[0045]
[0046] Compound 1 828mg (molecular formula: C 12 H 5 BrO 3 ) (3.0 mmol) was dissolved in ethanol, and then 1.95 g of aminoethylmorpholine (15.0 mmol) was added, the reaction solution was heated to about 80° C., and the reaction was stirred for 1 hour. After the reaction is complete, the solvent (ethanol) is removed by suction filtration to obtain the product. Without column purification, 1.1 g of white solid was obtained (the yield was 95%), and the obtained solid was compound 2.
[0047] Synthesis of compound 3:
[0048]
[0049] Compound 2 970mg (molecular formula: C 18 H 17 BrN 2 O 3 )(2.5mmol), K 2 CO 3 518 mg (3.75 mmol) was dissolved in DMSO, the reaction solution was heated to about 80°C, and the reaction was stirred for 6 hours. After the reaction is completed, the reaction solution is cooled to room temperature, poured into ice water, the pH is adjusted with HCl until a large amount of solid precipitates, and the product is obtai...
Embodiment 2
[0057] Fluorescence spectrum changes of probe IX reacting with different equivalents of formaldehyde
[0058] Take the probe IX prepared in Example 1 and dissolve it in DMSO to prepare a probe mother solution with a concentration of 1 mmol / L (the concentration of probe IX is 1 mmol / L); add a 37% formaldehyde solution to distilled water to prepare The formaldehyde mother liquor with a formaldehyde concentration of 100mmol / L is sequentially diluted to the required concentration. Take 30μL from the probe mother liquor and add it to a 10mL centrifuge tube, add different equivalents (0-200eq) of the formaldehyde mother liquor (the equivalent refers to the moles of formaldehyde in the formaldehyde mother liquor relative to the moles of the probe in the probe mother liquor The test solution is diluted to 3 mL with 0.57 mL DMSO and different volumes of PBS aqueous solution (concentration 25 mmol / L, pH 7.4), the probe concentration is 10 μM, and the test solution containing 20% DMSO. U...
Embodiment 3
[0060] Fluorescence changes of probe IX and formaldehyde over time
[0061] Take 30μL from the fluorescent probe mother solution in Example 2 and add it to a 10mL centrifuge tube, add 30μL of formaldehyde mother solution with a concentration of 1mmol / L, and then add 0.57mL DMSO and 2.40mL PBS aqueous solution (concentration 25mmol / L, pH7. 4) Prepare a probe test solution with a concentration of 10 μM, a formaldehyde concentration of 2 mM, and 20% DMSO. Use the excitation wavelength of 395nm to test the fluorescence spectrum that changes with time. by Figure 4 As shown, as time increases, the fluorescence intensity at 518nm gradually increases, and the fluorescence intensity reaches the maximum at 200 min.
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