Ratio two-photon and near-infrared HClO detection fluorescence probe as well as preparation and application thereof

A technology of near-infrared detection and fluorescent probe, which is applied in the direction of fluorescence/phosphorescence, luminescent materials, measuring devices, etc., can solve the problems of not realizing HClO ratio two-photon and near-infrared detection, and achieve simple structure, simple probe structure, The effect of high sensitivity

Active Publication Date: 2018-12-07
SHANDONG NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Characteristics of ratiometric two-photon and near-infrared detection without HClO concentration detection

Method used

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  • Ratio two-photon and near-infrared HClO detection fluorescence probe as well as preparation and application thereof
  • Ratio two-photon and near-infrared HClO detection fluorescence probe as well as preparation and application thereof
  • Ratio two-photon and near-infrared HClO detection fluorescence probe as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] 1) Synthesis of compound Cou-1:

[0061] Under argon protection, in a 50mL two-necked flask, 4-(diethylamino) salicylaldehyde (3.86g, 20mmol) was dissolved in 20mL of absolute ethanol, and then ethyl acetoacetate (2.50ml , 20mmol), piperidine (200μL, 2mmol), heated to 80°C and refluxed for 4.5-5.5h, after the reaction was completed, an orange solution was obtained, left to stand, cooled, yellow crystals were precipitated, filtered under reduced pressure, washed with ice ethanol to obtain A bright yellow solid was recrystallized twice from absolute ethanol to obtain 3.28 g of pure compound Cou-1, with a conversion rate of 63.32%.

[0062] 2) Synthesis of compound Cou-2:

[0063] Compound Cou-1 (259.30 mg, 1 mmol) and 4-diethylaminobenzaldehyde (177 mg, 1 mmol) were dissolved in 8 mL of absolute ethanol, a catalytic amount of piperidine was added dropwise, and refluxed at 80°C overnight to obtain a dark red reaction solution. After the reaction mixture was spin-dried, t...

Embodiment 2

[0073] 1) Synthesis of compound Cou-1:

[0074] Under argon protection, in a 50mL two-necked flask, 4-(diethylamino) salicylaldehyde (3.86g, 20mmol) was dissolved in 20mL of absolute ethanol, and then ethyl acetoacetate (2.50ml , 20mmol), piperidine (200μL, 2mmol), heated to 80°C and refluxed for 4.5-5.5h, after the reaction was completed, an orange solution was obtained, left to stand, cooled, yellow crystals were precipitated, filtered under reduced pressure, washed with ice ethanol to obtain The bright yellow solid was recrystallized twice from absolute ethanol to obtain 3.28 g of pure compound Cou-1, and the conversion rate was 63.32%.

[0075] 2) Synthesis of compound Cou-2:

[0076] Compound Cou-1 (259.30 mg, 1 mmol) and 4-diethylaminobenzaldehyde (177 mg, 1 mmol) were dissolved in 8 mL of absolute ethanol, a catalytic amount of piperidine was added dropwise, and refluxed at 80°C overnight to obtain a dark red reaction solution. After the reaction mixture was spin-drie...

Embodiment 3

[0081] The probe Cou-4 used in Example 3 and Example 4 was prepared from Example 1.

[0082] Example 3

[0083] Probe response experiment to HClO:

[0084] First, the change in absorption of the probes was investigated. Cou-4 (10 μ M) measured the absorption spectrum change when responding to series concentration HClO (0-50 μ M) in PBS buffer solution (0.05M, pH=7.4), the experimental results are as follows figure 1 Shown: As the concentration of HClO added to Cou-4 (10μM) increases, the absorption peak at 450nm decreases gradually, the absorption peak at 580nm increases gradually, and an isoabsorptive point appears at 475nm.

[0085]Then, the fluorescence response of the probes to HClO was investigated. The fluorescence spectrum changes of Cou-4 (10μM) in PBS buffer solution (0.05M, pH=7.4) were measured in response to series concentrations of HClO (0-50μM), and the excitation wavelength was 475nm. Experimental results such as figure 2 , image 3 Shown: along with the ...

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Abstract

The invention relates to a ratio two-photon and near-infrared HClO detection fluorescence probe as well as preparation and application thereof and belongs to the technical fields of synthesis and detection. The structural formula of the fluorescence probe is as shown in the specification. The fluorescence probe is prepared by the following steps: 1, reacting 4-(diethylamino) salicylaldehyde with ethyl acetoacetate and piperidine; 2, enabling 4-diethylaminobenzaldehyde to participate in the reaction; and 3, enabling cyclohexene to participate in the reaction to obtain a compound, respectively reacting the compound with lithium diisopropylamide and phenylselenenyl bromide, thereby obtaining the fluorescence probe. The probe can be reacted with the HClO to produce olefinic bonds, wavelength red shift is caused by the enlarged conjugated structure, and the ratio fluorescence change of which the short wavelength fluorescence intensity is reduced and long wavelength fluorescence intensity isenhanced is formed. Therefore, the design of the probe based on the Sharpless alkene synthesis reaction can be used for detecting the HClO, and the probe is simple in structure and has the advantagesof being high in selectivity, high in sensitivity, fast in transient response and the like.

Description

technical field [0001] The invention belongs to the technical field of synthesis and detection, and in particular relates to a fluorescent probe for ratiometric two-photon and near-infrared detection of HClO, its preparation and application. Background technique [0002] Hypochlorous acid (HClO) can be used as a disinfectant and oxidant in physiological processes. Endogenous HClO is usually the myeloperoxidase (MPO) secreted by immune cells during inflammatory reactions that catalyzes the generation of chloride ions and hydrogen peroxide. produced by oxidation reactions. In addition, more and more research results have shown that, in addition to phagosomes that can produce HClO under the stimulation of pathogens, non-phagosomes can also produce HClO under the induction of various soluble stimuli. The normal content of HClO can protect the organism. The imbalance of HClO, especially the excessive generation of HClO, will oxidize and destroy various biological functional mole...

Claims

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Application Information

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IPC IPC(8): C07D311/16C09K11/06G01N21/64
CPCC07D311/16C09K11/06C09K2211/1007C09K2211/1088G01N21/6428G01N21/6486
Inventor 唐波王栩吴田宏解希雷李勇焦晓云赵志文
Owner SHANDONG NORMAL UNIV
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