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A ratiometric fluorescent probe capable of simultaneously detecting silver ions and trivalent chromium ions and its preparation method and application

A fluorescent probe and ion detection technology, applied in the field of analysis and detection, to reduce the impact and improve the detection accuracy

Inactive Publication Date: 2019-06-18
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, multi-purpose probes that can simultaneously realize the response recognition function of multiple metal ions are of great significance in practical applications. So far, no fluorescent detection system that can simultaneously detect silver ions and trivalent chromium ions has been reported.

Method used

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  • A ratiometric fluorescent probe capable of simultaneously detecting silver ions and trivalent chromium ions and its preparation method and application
  • A ratiometric fluorescent probe capable of simultaneously detecting silver ions and trivalent chromium ions and its preparation method and application
  • A ratiometric fluorescent probe capable of simultaneously detecting silver ions and trivalent chromium ions and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1: Preparation process 1 of fluorescent probe

[0037] 1) Dissolve 186mg of 1-pyrenecarboxylic acid (0.75mmol) in 0.75mL of N,N-dimethylformamide, add 132mg of 3-bromopropyne (1.125mmol) and 154mg of potassium carbonate (1.125mmol), and control the reaction temperature at 80°C, stirred and reacted for 5 hours; cooled to room temperature, added 20 mL of deionized water, extracted with 100 mL of ethyl acetate, collected the organic phase, washed with brine (50 g / L), dried with 100 mg of anhydrous sodium sulfate, and filtered The organic solvent was removed by rotary evaporation, and the resulting solid was purified by silica gel chromatography (eluent: sherwood oil / dichloromethane, V / V=4:1) to obtain white solid 1-pyrenecarboxylate-1-propynyl ester ( The productive rate is 93.0%); The product is characterized by NMR 1 H NMR (CDCl 3 ,600MHz,δppm):9.28-9.30(d,1H),8.65-8.70(d,1H),8.23-8.28(q,3H),8.15-8.19(t,2H),8.04-8.09(q,2H) , 5.11-5.13 (d, 2H), 2.58-2.60 (t,...

Embodiment 2

[0041] Embodiment 2: the preparation process flow 2 of fluorescent probe

[0042] 1) Dissolve 93mg of 1-pyrenecarboxylic acid (0.375mmol) in 0.66mL of N,N-dimethylformamide, add 88.4mg of 3-bromopropyne (0.75mmol) and 128mg of potassium carbonate (0.94mmol), and control the reaction temperature Stir the reaction at 92.5°C for 6 hours; cool to room temperature, add 10 mL of deionized water, extract with 50 mL of ethyl acetate, collect the organic phase, wash the organic phase with brine (50 g / L), and dry with 50 mg of anhydrous sodium sulfate. Filtration; the organic solvent was removed by rotary evaporation, and the resulting solid was purified by silica gel column chromatography (eluent: petroleum ether / dichloromethane, V / V=4:1) to obtain a white solid 1-pyrenecarboxylate-1-propynyl ester (92.1% yield).

[0043] 2) Take 217mg of triethylene glycol (1.45mmol) and dry it in an oven at 107.5°C for 2.5 hours, dissolve it in 25.4mL of dichloromethane, add 0.66g of 4-dimethylamino...

Embodiment 3

[0047] Embodiment 3: the preparation process flow 3 of fluorescent probe

[0048] 1) Dissolve 232.5mg of 1-pyrenecarboxylic acid (0.938mmol) in 2.4mL of N,N-dimethylformamide, add 276mg of 3-bromopropyne (2.35mmol) and 472mg of potassium carbonate (3.28mmol), and control the reaction temperature Stir the reaction at 105°C for 7 hours; cool to room temperature, add 25 mL of deionized water, extract with 125 mL of ethyl acetate, collect the organic phase, wash the organic phase with brine (50 g / L), and dry with 125 mg of anhydrous sodium sulfate. Filtration; the organic solvent was removed by rotary evaporation, and the resulting solid was purified by silica gel column chromatography (eluent: petroleum ether / dichloromethane, V / V=4:1) to obtain a white solid 1-pyrenecarboxylate-1-propynyl ester (93.5% yield).

[0049] 2) Take 542.5mg of triethylene glycol (3.62mmol) and dry it in an oven at 120°C for 3 hours, dissolve it in 72mL of dichloromethane, add 1.9g of 4-dimethylaminopyr...

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Abstract

The invention discloses a ratio-type fluorescent probe for simultaneously detecting silver ions and trivalent chromic ions as well as a preparation method and application of the ratio-type fluorescent probe. The fluorescent probe is of a symmetric structure of pyrene-diIL-pyrene and triazole connected by triethylene glycol; when no detected ions exist in a system, the system emits a characteristic fluorescence emission band of an excimer of pyrene when emitting light with specific wavelength is excited; when the silver ions and the trivalent chromic ions are separately added in the system, two detected ions and a recognition group form a complex with a specific structure by different interactions, and an excimer structure of a probe molecule is damaged, thereby separately realizing ratio-type fluorescent detection of the silver ions and the trivalent chromic ions and avoiding the interference of outside conditions in the analysis and detection process. According to the ratio-type fluorescent probe disclosed by the invention, different responses of the silver ions and the trivalent chromic ions in a buffer solution can be distinguished with naked eyes under the irradiation of a portable ultraviolet lamp, and is expected to be used for quantitative analysis of the silver ions and the trivalent chromic ions in samples such as chemical samples and environmental samples.

Description

technical field [0001] The invention relates to a fluorescent probe compound, in particular to a ratio-type fluorescent probe which can be used for the detection of silver ions and trivalent chromium ions at the same time, as well as its preparation method and application, belonging to the technical field of analysis and detection. Background technique [0002] Transition metals and heavy metals widely exist in nature and are very important for maintaining ecological balance. Chromium is one of the essential trace elements for the human body. It plays an important role in the normal development of the human body and the regulation of blood sugar. When the human body lacks chromium, there will be disorders of sugar metabolism, and severe cases will suffer from diseases such as diabetes and uremia; on the contrary, if the human body takes in chromium If the amount of chromium is too high, it will cause lesions of the kidneys, liver and nervous system; in industry, chromium can...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D249/04C09K11/06G01N21/64
CPCC07D249/04C09K11/06C09K2211/1011C09K2211/1059G01N21/6428
Inventor 余昌敏杨文化吴水珠吴春先曾钫
Owner SOUTH CHINA UNIV OF TECH
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