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Colorimetric/fluorescent probe for detecting hypochlorite ions as well as preparation method and application of colorimetric/fluorescent probe

A fluorescent probe and hypochlorite technology, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of rare ClO-real-time quantitative fluorescence imaging, and achieve real-time quantitative fluorescence imaging and synthetic routes Short, easy cell staining effect

Active Publication Date: 2021-11-05
CHINA UNIV OF MINING & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, some currently designed and reported for ClO - Few probes for fluorescence imaging can realize the detection of ClO in biological systems - Real-time quantitative fluorescence imaging

Method used

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  • Colorimetric/fluorescent probe for detecting hypochlorite ions as well as preparation method and application of colorimetric/fluorescent probe
  • Colorimetric/fluorescent probe for detecting hypochlorite ions as well as preparation method and application of colorimetric/fluorescent probe
  • Colorimetric/fluorescent probe for detecting hypochlorite ions as well as preparation method and application of colorimetric/fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Embodiment 1: the synthesis of probe compound TPE-acylamide-Rh

[0042] Weigh 0.50g (1.33mmol) of 1-(4-formylphenyl)-1,2,2-triphenylethylene and add it to 5mL of thionyl chloride solution, heat to reflux for 4h; sulfoxide solution. When the temperature dropped to room temperature, 30 mL of acetonitrile solution was added, followed by 1 mL of triethylamine; finally, 0.62 g (1.37 mmol) of rhodamine B hydrazide was weighed and added to the reaction solution, under nitrogen protection, heated to reflux, and reacted overnight. After the reaction was completed, the reaction solution was poured into water, extracted three times with dichloromethane, the organic phases were combined, dried over anhydrous magnesium sulfate, and spin-dried to obtain a crude product, using dichloromethane: methanol volume ratio of 30:1 as mobile phase, passing through silica gel The column yielded 0.35 g of pure product, yield: 31.4%, melting point: 173-175°C. Hydrogen spectrum such as figure 1...

Embodiment 2

[0043] Example 2: Ratio-type fluorescence characteristics and AIE properties of the probe TPE-acylamide-Rh

[0044] The probe TPE-acylamide-Rh is a ClO with AIE characteristics linked by tetraphenylethylene and rhodamine B through an amide bond - fluorescent probe. The recognition site of the probe TPE-acylamide-Rh is the rhodamine amide structure, which is in the ClO - Under the action of strong oxidation, the amide bond is broken, the rhodamine spirocycle undergoes a "ring-opening reaction", and the colorimetry / fluorescence of the probe changes. The probe TPE-acylamide-Rh exhibits the fluorescence of tetraphenylethylene in the aggregated state, and when mixed with ClO - After the reaction, the tetraphenylethylene aggregation-induced luminescence of the probe disappears, showing the fluorescence of the rhodamine structure, becoming a typical ratiometric fluorescent probe.

[0045] The probe TPE-acylamide-Rh exhibits typical aggregation-induced luminescent properties (e.g. ...

Embodiment 3

[0046] Embodiment 3: Solvent ratio selection of probe TPE-acylamide-Rh

[0047] TPE-acylamide-Rh is a reactive ClO - For fluorescent probes, the choice of solvent ratio affects the sensitivity of the probe. Test the addition of ClO to ethanol-water systems with different water contents - Fluorescence intensity to explore the optimal solvent ratio, the results are as follows Figure 5 shown. The water content of TPE-acylamide-Rh solution is between 0% and 50%, in a dissolved state, no fluorescence emission, in ClO - Under the action, a fluorescence emission peak appears at 583nm, and the intensity of the emission peak is the largest when the water content is 50%, indicating that: TPE-acylamide-Rh is in solution state for ClO - Has good sensitivity, in the ethanol-water system with a water content of 50%, for ClO - The response sensitivity is the highest. Therefore, TPE-acylamide-Rh reacts to ClO in solution state - The identified solvent ratio is 50% ethanol-water syste...

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Abstract

The invention relates to a colorimetric / fluorescent probe for detecting hypochlorite ions as well as a preparation method and application thereof. The fluorescent probe is named as TPE-acylamide-Rh, and the chemical structural formula of the fluorescent probe is as shown in a formula I. The preparation method comprises the following steps: dissolving 1-(4-phenylformate)-1,2,2-triphenylethylene in thionyl chloride, conducting heating for a reaction, performing reacting with rhodamine B hydrazide under inert atmosphere and catalytic action, and carrying out purifying to obtain the fluorescent probe. The probe shows excellent selectivity, ion interference resistance and sensitivity on ClO<-> recognition performance in a solution state and an aggregation state. In addition, the probe forms nanoparticles in the aggregation state, so cell staining is easy, and cell imaging application is facilitated. Hela cell imaging research shows that the TPE-acylamide-Rh shows an excellent characteristic of identifying ClO<-> in cells. The preparation method for the probe is simple in process and short in synthesis route. The probe is applied to detection of hypochlorite ions, and the application range of the probe is widened.

Description

technical field [0001] The invention belongs to the field of organic fluorescent molecular probes, in particular to a colorimetric / fluorescent probe for detecting hypochlorite ions and a preparation method and application thereof. Background technique [0002] Hypochlorous acid, as a strong oxidant, is widely used in tap water disinfection and clothing bleaching in daily life; it is also an important active oxygen small molecule in organisms, participating in the immune regulation, antigen response, and signal transduction of organisms and cell apoptosis. break ClO - Balance can trigger various cardiovascular diseases, tissue inflammation and even cancer. Therefore, in order to prevent from ClO - Threats to study rapid, efficient, and accurate detection of ClO in the environment and in vivo - method is urgently needed. [0003] with conventional ClO - Compared with detection methods (iodometric method, coulometric method, polarographic method, electrochemical method, p...

Claims

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Application Information

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IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC07D491/107C09K11/06G01N21/6428C09K2211/1007C09K2211/1033G01N2021/6443G01N2021/6417
Inventor 张然苗保喜赵鑫榆倪中海
Owner CHINA UNIV OF MINING & TECH
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