Alpha-naphtholphthalein derivative multifunctional fluorescent probe as well as preparation method and application thereof

A technology of fluorescent probes and derivatives, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of complex synthesis steps, low sensitivity, large molecular weight, etc., and achieve strong anti-interference ability and simple preparation method High efficiency and excellent selectivity

Active Publication Date: 2021-11-19
SHENZHEN INST OF ADVANCED TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reported small molecule fluorescent probes still have problems such as complex synthesis steps, large molecular weight, and low sensitivity. Therefore, a small mol...

Method used

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  • Alpha-naphtholphthalein derivative multifunctional fluorescent probe as well as preparation method and application thereof
  • Alpha-naphtholphthalein derivative multifunctional fluorescent probe as well as preparation method and application thereof
  • Alpha-naphtholphthalein derivative multifunctional fluorescent probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0046] The steps of the preparation method of the above-mentioned α-naphtholphthalein derivatives multifunctional fluorescent probe are as follows:

[0047] (1) The compound of formula (III) is dissolved in trifluoroacetic acid, then hexamethylenetetramine is added, and the compound of formula (II) is generated under nitrogen atmosphere at 70-110°C, with a yield of 50%-80%.

[0048](2) Dissolving the compound of formula (II) in a mixed solvent of dichloromethane and ethanol, then adding diaminomaleonitrile (diaminomaleonitrile) dissolved in a mixed solvent of dichloromethane and ethanol, while dropping After adding glacial acetic acid, and reacting for 2-8 hours, after extraction and column chromatography separation and purification, α-naphtholphthalein derivatives multifunctional fluorescent probes are obtained with a yield of 65%-85%.

[0049] The present invention also provides a method for detecting Hg using α-naphtholphthalein derivatives multifunctional fluorescent probe...

Embodiment 1

[0052] Example 1 Synthesis of α-naphtholphthalein derivatives multifunctional fluorescent probe (I)

[0053] The reaction formula of synthetic α-naphtholphthalein derivatives multifunctional fluorescent probe (I) is as follows:

[0054]

[0055] The specific steps of synthetic α-naphtholphthalein derivatives multifunctional fluorescent probe (I) are as follows:

[0056] (1) Dissolving the formula (III) in trifluoroacetic acid, and then gradually adding urotropine (hexamethylenetetramine). Under the protection of nitrogen, heat and reflux at 70-110° C. for 2-8 hours, and then cool the reaction system to room temperature. Separate, wash, dry, and filter after standing. The resulting filtrate was spin-dried with a rotary evaporator to obtain a crude product; finally, the crude product was separated and purified by column chromatography and then spin-dried with a rotary evaporator to obtain the pure product formula (II), with a yield of about 50% to 80%. The mass spectrometr...

Embodiment 2

[0058] Embodiment 2 fluorescent probe of the present invention is paired with Hg 2+ and Al 3+ selective detection of

[0059] 10 μmol / L α-naphtholphthalein derivatives multifunctional fluorescent probe (fluorescent probe (I) prepared in embodiment 1) dimethyl sulfoxide and water have a volume ratio of 9:1 mixed solution, add 100 μmol / L respectively Metal ions of L (Zn 2+ ,Mg 2+ , Ca 2+ ,Co 2+ ,Fe 3+ , Ni 2+ ,Sn 2+ ,Cd 2+ , Li + , Na + ,Pb 2+ ,Mn 2+ , Fe 2+ ,VO 2+ ,Cu 2+ ). After 15 minutes, detect the changes in the fluorescence emission spectrum and the ultraviolet-visible absorption spectrum of the solution, and the detection results are as follows: Figure 4 and Figure 5 shown. The α-naphtholphthalein derivatives multifunctional fluorescent probe has almost no emission peaks at 520nm and 480nm, and almost no absorption peak at 436nm. When Al 3+ After that, the α-naphtholphthalein derivatives multifunctional fluorescent probe showed a strong emission pea...

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Abstract

The invention discloses an alpha-naphtholphthalein derivative multifunctional fluorescent probe as well as a preparation method and application thereof. The structural formula of the fluorescent probe is shown as a formula (I) in the description. A compound shown in a formula (II) is synthesized from a compound shown in the formula (III), and then the fluorescent probe is synthesized. The fluorescent probe can identify and detect Hg < 2 + > and Al < 3 + > in a mixed solution of dimethyl sulfoxide and water by using a fluorescence spectrum and/or an ultraviolet-visible absorption spectrum. The fluorescent probe has high selectivity and sensitivity for identifying Hg < 2 + > and Al < 3 + >, is strong in anti-interference capability and has very low detection limit; and the fluorescent probe can be used for qualitative and quantitative detection of Hg < 2 + > and Al < 3 + > and tracing imaging detection of Hg < 2 + > and Al < 3 + > in living cells.

Description

technical field [0001] The invention relates to the technical field of detection and identification of heavy metal ions, in particular to a multifunctional fluorescent probe of α-naphtholphthalein derivatives and its preparation method and application. Background technique [0002] With the development of the economy and the improvement of human health and environmental protection awareness, the problem of heavy metal pollution has received more and more attention. Heavy metal ions are mainly enriched in animals and plants through soil, water and other media, and gradually invade the human body. Because it is difficult to be biodegraded, it seriously threatens people's life and health. Mercury entering the human body can cause digestive tract, kidney, brain, and especially nervous system diseases, leading to extremity pain, Alzheimer's disease, Minamata disease, etc. Aluminum has the advantages of low density, good ductility, and strong corrosion resistance, and is widely ...

Claims

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Application Information

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IPC IPC(8): C07D307/88C09K11/06G01N21/64
CPCC07D307/88C09K11/06G01N21/6428G01N21/6456G01N21/6447C09K2211/1011C09K2211/1088
Inventor 张鹏飞张秀文江道勇龚萍王勇蔡林涛
Owner SHENZHEN INST OF ADVANCED TECH
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