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A Fluorescent Probe for Recognizing Thiophenol

A fluorescent probe, thiophenol technology, applied in the field of chemical analysis and detection, to achieve the effects of good cell membrane penetration, wide application range and low cytotoxicity

Active Publication Date: 2021-01-05
惠州广瑞合新材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are few reports of thiophenol fluorescent probes with long-wavelength emission, large Stokes shift and fast response.

Method used

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  • A Fluorescent Probe for Recognizing Thiophenol
  • A Fluorescent Probe for Recognizing Thiophenol
  • A Fluorescent Probe for Recognizing Thiophenol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment 1: the synthesis of compound 2

[0027] Compound 1 (3.32g, 10.0mmol) was dissolved in 50mL of ethylene glycol monomethyl ether, heated to 115°C until the reaction solution became clear, and then 3.0mL of hydrazine hydrate (80%) was added dropwise to the above mixed solution. After the addition was complete, the mixture was heated to reflux for 3 hours. After the reaction was completed, it was cooled to room temperature, and a large amount of orange precipitate was precipitated, which was filtered and washed to obtain compound 2. Yield: 2.32 g; Yield: 81.9%.

Embodiment 2

[0028] Embodiment 2: the synthesis of compound 3

[0029] Intermediate 2 (1.98g, 7mmol) was dissolved in 3-methyl-2-butanone (100mL), and then 3mL of concentrated sulfuric acid was slowly added dropwise, and the reaction mixture was refluxed and stirred for 4 hours under nitrogen protection. After the reaction was completed, , 3-methyl-2-butanone was removed by rotary evaporation under reduced pressure to obtain a crude product, which was separated and purified by silica gel column chromatography (petroleum ether / dichloromethane=1 / 10, v / v) to obtain product 3 as a pale yellow solid. Yield: 1.13 g; Yield: 48.5%.

Embodiment 3

[0030] Embodiment 3: the synthesis of compound 4

[0031] Compound 3 (1.0g, 3mmol) and p-Hydroxybenzaldehyde (0.37g, 3mmol) were dissolved in 20mL of dry toluene, stirred and mixed, and then glacial acetic acid (0.02mL) and piperidine (0.05mL) were added dropwise to the above mixture solution, after the dropwise addition, the mixed solution was refluxed and stirred for 6 hours under the protection of nitrogen, and the toluene was evaporated to dryness under reduced pressure to obtain a crude product, which was separated and purified by column chromatography (ethanol / dichloromethane=1 / 50, v / v ) to obtain product 4 as a red solid. Yield: 0.68 g; Yield: 51.7%.

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Abstract

The invention discloses a fluorescence probe used for rapid identification of phenylthioalcohol (PhSH), and applications thereof, and belongs to the technical field of chemical analysis detection. Thestructure formula of the fluorescence probe is disclosed in the invention; the fluorescence probe is high in selectivity and sensitivity, excellent in anti-interference capability, is capable of emitting red light, and is large in Stokes shift. The tissue penetrability of long wavelength emission (red light or near infrared light) is excellent, and background interference is low; large Stokes shift is capable of reducing self absorption and autofluorescence interference, and increasing detection sensitivity. The above excellent performance shows that the application value of the fluorescenceprobe in the field of environment and biological detection is high.

Description

technical field [0001] The invention belongs to the technical field of chemical analysis and detection, and in particular relates to the preparation of a fluorescent probe for detecting thiophenol and the application of the probe in detecting thiophenol. Background technique [0002] Thiophenol, also known as mercaptobenzene, is an important chemical raw material widely used in the synthesis of pesticides, polymer materials and drugs. Thiophenol has a foul smell and is a highly toxic compound. Studies have shown that the lethal concentration (LC50) for fish is 0.1-0.4mM, and the semi-lethal dose (LD50) for mice is 46.2mg / kg (oral) and 2.15mg / kg (subcutaneous injection). When people are exposed to the atmosphere of thiophenol, it has a strong irritating effect on the eyes, mucous membranes, respiratory tract and skin. After inhalation, it can cause throat, bronchospasm, edema, chemical pneumonia, and pulmonary edema, resulting in death. Poisoning symptoms include burning se...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/06G01N21/64
CPCC07D471/06G01N21/643G01N21/6486
Inventor 刘兴江周爽魏柳荷肜一帆孙爱灵张文英
Owner 惠州广瑞合新材料科技有限公司
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