Dibromofluorescein derivative as well as synthetic method and application thereof

A technology of dibromofluorescein and its synthesis method, which is applied in the application field of dibromofluorescein derivatives and its synthesis, and detection of Al3+, achieving the effects of high sensitivity, high specificity and simple synthesis steps

Active Publication Date: 2019-11-26
SHANXI UNIV
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AI-Extracted Technical Summary

Problems solved by technology

However, too much aluminum can lead to various physiological and biochemical probl...
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Abstract

The invention discloses a dibromofluorescein derivative as well as a synthetic method of the derivative and an application of the derivative in detecting Al<3+>, and belongs to the technical field ofdetection of fluorescein derivatives and aluminum ions. The synthetic method of the dibromofluorescein derivative comprises the following steps: 1) dissolving hydrazine hydrate and dibromofluoresceininto methanol, and performing heating reflux to obtain a crude product; and performing rotary evaporation on the crude product, performing vacuum drying, and performing recrystallization by using methanol to obtain dibromofluorescein hydrazide; and 2) dissolving the dibromofluorescein hydrazide and 2-hydroxy-5-nitrobenzaldehyde into an absolute ethanol solution, performing heating reflux to obtaina crude product, performing rotary evaporation on the crude product, performing vacuum drying, performing recrystallization by using methanol, and performing drying to obtain the off-white solid powder 5-nitrosalicylaldehyde dibromofluorescein hydrazone (NDH). The invention also provides a method for detecting the aluminum ions. The method comprises the following step of quantitatively detectingthe content of the Al<3+> in a THF:H2O (9:1, v/v) solution by using the dibromofluorescein derivative as a probe. The detection method provided by the invention can detect the aluminum ions with highselectivity and high sensitivity, is simple and convenient to operate, and can be applied to cell imaging.

Application Domain

Organic chemistryMaterial analysis by observing effect on chemical indicator +3

Technology Topic

Aluminum IonReflux +12

Image

  • Dibromofluorescein derivative as well as synthetic method and application thereof
  • Dibromofluorescein derivative as well as synthetic method and application thereof
  • Dibromofluorescein derivative as well as synthetic method and application thereof

Examples

  • Experimental program(7)

Example Embodiment

[0029] Example 1 Synthesis and characterization of fluorescent probe NDH
[0030] (1) Weigh 3.4g (9.1mmol) of dibromofluorescein and 1mL (20mmol) of hydrazine hydrate solution and dissolve them in 10mL of methanol, and react at 65°C for 4 hours. After the reaction is completed, cool to room temperature, then rotate and evaporate. Dry and recrystallize from methanol to obtain a pink solid.
[0031] (2) Weigh 0.019g (0.05mmol) of the product obtained above and 0.0075g (0.05mmol) of 2-hydroxy-5-nitrobenzaldehyde into 10mL of absolute ethanol, and ultrasonicate for 5min to dissolve, then stir for 65 Reflux at °C for 4 hours, cool to room temperature after the reaction is completed, then rotate and evaporate and vacuum dry, and then recrystallize with methanol to obtain an off-white solid powder. 1H NMR(600MHz,DMSO)δ12.23(s,1H),9.97(s,2H),9.11(s,1H),8.72(d,J=2.8Hz,1H), 8.28(d,J=9.1Hz ,1H),7.99(d,J=32.5Hz,1H), 7.18(d,J=9.1Hz,1H), 7.00(d,J=9.3Hz,1H), 6.68(d,J=8.8Hz,1H ), 6.43 (q, J=8.6 Hz, 4H); FT-IR (KBr), σ/cm-1: 3423 (-OH), 1631 (-C=N).

Example Embodiment

[0032] Example 2 Fluorescent probe NDH is used for Al 3+ UV absorption measurement
[0033] Take 20μL of fluorescent probe NDH storage solution in a clean colorimetric tube, dilute it to 2mL with THF: phosphate buffer solution (9:1), scan the absorption spectrum on the UV-Vis spectrophotometer, it can be observed in the visible light region Absorption at 443nm, add Al 3+ After that, the absorption peak at 443nm disappeared. figure 1 , And the color of the solution changes from yellow to colorless, and the presence of aluminum ions can be identified with the naked eye.

Example Embodiment

[0034] Example 3 Fluorescent probe NDH is used for Al 3+ Fluorescence spectrometry
[0035] Take 20μL of fluorescent probe NDH storage solution in a clean colorimetric tube, dilute it to 2mL with THF: phosphate buffer solution (9:1), and detect on a fluorometer. When the excitation wavelength is 445nm, dibromofluorescein The derivative has an emission peak at 600nm, when Al is added 3+ After that, the intensity of the fluorescence emission peak at 600nm gradually decreases. figure 2.

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