A formaldehyde fluorescent probe based on heptamethine indocyanine and its preparation method and use method
A technology of fluorescent probe and indocyanine, which is applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of long analysis time, complicated sample preparation procedures, and easy interference of analysis results, and achieve low cost , good selectivity, and the synthesis process is simple and easy to operate
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Embodiment 1
[0040] Example 1: Preparation of probe HCy1
[0041] 1) Add 1,1,2-trimethyl-1H-benzo[e]indole (1.19g, 5mmol) and methyl iodide (1.08g, 5mmol) (molar ratio 1:3) into a three-necked flask, And add the solvent acetonitrile to make it dissolve completely. The solution was refluxed for 10 hours under a nitrogen atmosphere. After the reaction was complete, it was cooled to room temperature, and the solvent was removed under reduced pressure. The residue was washed 3 times with ether, and dried to obtain compound 1 (1.7 g) as a white powder with a yield of 85%.
[0042] 1H NMR (400MHz, DMSO) δ8.38(d, J=8.3Hz, 1H), 8.34–8.28(m, 1H), 8.23(d, J=8.1Hz, 1H), 8.11(d, J=8.9Hz ,1H), 7.80(s,1H), 7.73(s,1H), 4.10(s,3H), 2.88(s,3H), 1.76(s,6H).
[0043] 2) Add N,N-dimethylformamide (DMF) (40mL, 0.5mmol) and dichloromethane (40mL) (1:3 molar ratio) into a three-necked flask, and cool at 0°C for 0.5 hours. Then, a mixed solvent of phosphorus oxychloride (37 mL) and dichloromethane (35 mL) was...
Embodiment 2
[0050] Example 2: Absorption and fluorescence titration experiments of different concentrations of formaldehyde on probe HCy1
[0051] The probe HCy1 synthesized above was dissolved in methanol solution to prepare a probe mother solution with a concentration of 1 mmol / L; the formaldehyde aqueous solution was diluted to formaldehyde mother solution with a concentration of 0.1 mmol / L. Take 12 parts of the probe mother solution with a volume of 10 μL, add 1 mL of methanol solution and different concentrations of formaldehyde respectively, dilute to 2 mL with the methanol solution, and prepare the probe concentration of 10 μmol / L and the concentration of formaldehyde of 0, 0.1, and 0.15 respectively. , 0.2, 0.25, 0.3, 0.35, 0.4, 0.45, 0.5, 1, 2mmol / L test solution. The changes of the absorption and fluorescence spectra of the probe HCy1 with the addition of different concentrations of formaldehyde were tested by ultraviolet spectrometer and fluorescence spectrometer respectively. ...
Embodiment 3
[0052] Example 3: Study on the Selectivity of Probe HCy1 to Different Interfering Analytes
[0053] Take 5 aliquots of 10 μL probe mother solution from the above, add formaldehyde, H 2 O, acetaldehyde, propionaldehyde and methylglyoxal solution, diluted to 2 mL with methanol solution. Prepare a test solution with a probe concentration of 10 μmol / L and an interfering analyte concentration of 0.1 mmol / L, and test the changes in the absorption spectrum of the solution after 5 minutes. Such as Figure 8 As shown, only the absorption intensity at 718nm of the test solution added with formaldehyde gradually decreases, while the absorption intensity at 804nm gradually increases. In order to more intuitively observe the changes in the UV-visible spectrum after the reaction of the fluorescent probe HCy1 with various analytes, the red-shifted wavelengths of the UV-visible spectrum are presented in the form of a histogram, as shown in Figure 9 shown.
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