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Ratio type fluorescent probe and preparation method thereof, and application of ratio type fluorescent probe in sulfite ion detection

A fluorescent probe, ratio-type technology, applied in the field of analysis and detection, can solve the problems of limited wide application, difficulty in ensuring detection accuracy, fluorescence quenching, etc., and achieve the effects of improving detection accuracy, reducing spontaneous interference, and high detection sensitivity

Active Publication Date: 2021-01-12
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these methods still have some disadvantages. For example, the enhanced and quenched fluorescent probes have large errors in the quantitative detection of sulfite, which are not as accurate as the ratiometric fluorescent probes.
At the same time, these probes are easily interfered by the environment or their own factors, making it difficult to guarantee the accuracy of detection
Another example is patent CN108129428A, which invented a ratiometric fluorescent probe for detecting sulfite, but the structure of the probe belongs to an obvious aggregation-inducing quenching group, so the phenomenon of fluorescence quenching will occur when the concentration is high. On the one hand, it is difficult to To ensure the accuracy of detection, on the other hand, it limits its wide application

Method used

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  • Ratio type fluorescent probe and preparation method thereof, and application of ratio type fluorescent probe in sulfite ion detection
  • Ratio type fluorescent probe and preparation method thereof, and application of ratio type fluorescent probe in sulfite ion detection
  • Ratio type fluorescent probe and preparation method thereof, and application of ratio type fluorescent probe in sulfite ion detection

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Take 423 mg of 3-(benzo[d]thiazol-2-yl)-4'-(diphenylamino)-[1,1'-biphenyl]-4-ol and 114.85 mg of levulinic acid in a single-necked flask, add 13.5 mL of dichloromethane was dissolved, the system was vacuum-filled with nitrogen and repeated three times, and stirred at room temperature for 10 minutes to obtain solution 1. Solution 2 was obtained by dissolving 445.53 mg of dicyclohexylcarbodiimide and 21.98 mg of 4-dimethylaminopyridine in 6.48 mL of dichloromethane. The solution 2 was injected into the solution 1 with a syringe, and reacted at room temperature for 15 hours. Add water and dichloromethane for extraction, take the organic phase, dry with anhydrous sodium sulfate, filter; remove the organic solvent by rotary evaporation, and purify the resulting solid by silica gel chromatography to obtain 3-(benzo[d]thiazol-2-yl)- 311 mg of 4'-(diphenylamino)-[1,1'-biphenyl]-4-yl 4-oxopentanoate (yield: 60.76%).

[0045] The product was characterized by proton nuclear magn...

Embodiment 2

[0047] Take 150 mg of 3-(benzo[d]thiazol-2-yl)-4'-(diphenylamino)-[1,1'-biphenyl]-4-ol and 37.03 mg of levulinic acid in a single-necked flask, add 1.6 mL of dichloromethane was dissolved, the system was vacuum-filled with nitrogen and repeated three times, and stirred at room temperature for 10 minutes to obtain solution 1. Solution 2 was obtained by dissolving 131.66 mg of dicyclohexylcarbodiimide and 3.90 mg of 4-dimethylaminopyridine in 1.28 mL of dichloromethane. The solution 2 was injected into the solution 1 with a syringe, and reacted at room temperature for 12 hours. Add water and dichloromethane for extraction, take the organic phase, dry with anhydrous sodium sulfate, filter; remove the organic solvent by rotary evaporation, and purify the resulting solid by silica gel chromatography to obtain 3-(benzo[d]thiazol-2-yl)- 114 mg of 4'-(diphenylamino)-[1,1'-biphenyl]-4-yl 4-oxopentanoate (yield: 63.11%). The product is characterized by proton nuclear magnetic resonanc...

Embodiment 3

[0050] Take 3-(benzo[d]thiazol-2-yl)-4'-(diphenylamino)-[1,1'-biphenyl]-4-ol 322mg and levulinic acid 83.46mg in a single-necked flask, add 6.85 mL of dichloromethane was dissolved, the system was vacuum-filled with nitrogen and repeated three times, and stirred at room temperature for 10 minutes to obtain solution 1. Solution 2 was obtained by dissolving 310.89 mg of dicyclohexylcarbodiimide and 12.55 mg of 4-dimethylaminopyridine in 3.77 mL of dichloromethane. The solution 2 was injected into the solution 1 with a syringe, and reacted at room temperature for 14 hours. Add water and dichloromethane for extraction, take the organic phase, dry with anhydrous sodium sulfate, filter; remove the organic solvent by rotary evaporation, and purify the resulting solid by silica gel chromatography to obtain 3-(benzo[d]thiazol-2-yl)- 229 mg of 4'-(diphenylamino)-[1,1'-biphenyl]-4-yl 4-oxopentanoate (yield: 58.87%). The product is characterized by proton nuclear magnetic resonance spec...

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Abstract

The invention relates to a ratio type fluorescent probe and a preparation method thereof, and application of the ratio type fluorescent probe in sulfite ion detection. The ratio type fluorescent probecan be used for detecting sulfite ions based on dual mechanisms of excited state intramolecular proton transfer and aggregation-induced emission. A fluorescent probe compound disclosed by the invention is 3-(benzo[d]thiazol-2-yl)-4'-(diphenylamino)-[1,1'-biphenyl]4-yl-4-oxopentanoate. The fluorescence probe has the outstanding characteristics that the fluorescence probe can realize the ratio typedetection of sulfite, the preparation method of the fluorescence probe is simple, the interference of an external environment on a detection result can be effectively avoided, and the fluorescence probe has high sensitivity and good selectivity. The fluorescent probe disclosed by the invention can be used for rapidly detecting sulfite ions in environment and food.

Description

technical field [0001] The invention relates to the technical field of analysis and detection, in particular to a ratiometric fluorescent probe, its preparation method and its application in the detection of sulfite ions. Background technique [0002] Sulfite ion (also known as sulfite) is widely used in food processing and brewing industry due to its ability to prevent oxidation, inhibit bacterial growth and control enzyme reactions. Sulfite ions (sulfites) are added to foods as preservatives to inhibit the growth of mold and bacteria. In the process of beer production, sulfite needs to be added as a powerful antioxidant to effectively maintain the flavor of beer, which is usually achieved by artificially adding sulfur dioxide. Similarly, in the wine industry, when the grapes are transported to the winery and before fermentation, an appropriate amount of sulfite is also required for antiseptic and antioxidative effects. In addition to artificial addition, yeast will also ...

Claims

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Application Information

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IPC IPC(8): C07D277/66C09K11/06G01N21/64
CPCC07D277/66C09K11/06G01N21/6428C09K2211/1014C09K2211/1037G01N2021/6432
Inventor 曾钫方奕畅陈俊杰吴水珠
Owner SOUTH CHINA UNIV OF TECH
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