Anthracene-thiosemicarbazide derivatives and their preparation methods and applications as fluorescent probes

A technology of thiosemicarbazide and derivatives, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., to achieve the effects of less cell damage, low excitation energy, and deeper penetration depth

Active Publication Date: 2021-04-02
SUZHOU UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There is no report on ion probes that can achieve upconversion fluorescence quenching response in the prior art

Method used

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  • Anthracene-thiosemicarbazide derivatives and their preparation methods and applications as fluorescent probes
  • Anthracene-thiosemicarbazide derivatives and their preparation methods and applications as fluorescent probes
  • Anthracene-thiosemicarbazide derivatives and their preparation methods and applications as fluorescent probes

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] In a 250ml three-necked flask, add 4-bromo-2-hydroxybenzaldehyde (2.84g, 11.19mmol), 9,10-diborate anthracene (2g, 4.73mmol) dissolved in 100ml 1,4-dioxane and 24ml ethanol, K 2 CO 3 (3.92 g, 28.38 mmol) was dissolved in 48 mL of distilled water and mixed into the above solution. Then, nitrogen gas was bubbled into the mixed solution for 15 minutes, and then tetrakis(triphenylphosphine) palladium (0) (0.39 g, 1.2 mmol) was added, and nitrogen gas was bubbled in for another 5 minutes, and the reaction was carried out at 120°C in a nitrogen atmosphere. During the reaction, The progress of the reaction was tracked by spotting the plate. The developer was dichloromethane:petroleum ether=1:1. After 48 hours of reaction, the spot of raw material 9,10-diborate anthracene almost disappeared, and the reaction was stopped. After the reaction was over, the reaction solution was distilled under reduced pressure to obtain a black solid mixture, and the organic phase was extracted...

Embodiment 2

[0039] The probe molecule of Example 1 was added to DMF, and the probe molecule DMF mother solution was prepared with a concentration of 1 mM.

[0040] Add 1.97 mL DMF solution and 1 mL buffered aqueous solution (the buffer solution is Na 2 HPO 4 / NaH 2 PO 4 , pH is 7, 1 / 2, v / v), then take 30 μL probe molecule DMF mother solution (concentration: 1mM) and add it to the above-mentioned quartz cuvette, ultrasonically dissolve it, and then prepare a 10 μM probe molecule Needle molecule solution.

[0041] Similarly, add 1.7 mL DMF solution and 1 mL buffered aqueous solution (Na 2 HPO 4 / NaH 2 PO 4 , pH is 7, 1 / 2, v / v), then take 300 μL of probe molecule DMF mother solution (concentration: 1mM) and add it to the above-mentioned quartz cuvette, ultrasonically dissolve it, and then prepare a 100 μM probe molecule Needle molecule solution.

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Abstract

The invention discloses an anthracene-thiosemicarbazide derivative, its preparation method and its application as a fluorescent probe. The preparation method comprises the following steps: 4-bromo-2-hydroxybenzaldehyde is prepared in a nitrogen atmosphere and an organic solvent React with 9,10-diborate anthracene to obtain an intermediate product I; then react the intermediate product I with thiosemicarbazide to obtain a copper ion fluorescent probe; the fluorescent probe of the present invention has an efficient upper, Downconverting Fluorescence Quenching Response Recognition Properties.

Description

technical field [0001] The invention belongs to the field of fluorescent reagents and the technical field of fluorescent probes for heavy metal ions, and specifically relates to an anthracene-thiosemicarbazide derivative probe and a preparation method thereof, and the application of the probe in detecting copper ions in water environments or organisms. The probe has the characteristic of upconverting fluorescence response. Background technique [0002] Copper ions (Cu 2+ ) Pollution has many hazards, it will not only affect the growth of animals and plants, microorganisms and the activity of soil enzymes, but also destroy the balance of the ecosystem. It will also accumulate in animals and plants, increase the toxicity of copper, and have adverse effects on human health. Detection of Cu 2+ has important practical significance. At present, there are many methods for the determination of copper ions, mainly including: spectrophotometry, fluorescence analysis, electrochemic...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C337/08C09K11/06G01N21/64
CPCC09K11/06G01N21/643C09K2211/1007C09K2211/1011G01N2021/6432C07C335/40
Inventor 王筱梅黄苏琴宋飒飒朱琳叶常青
Owner SUZHOU UNIV OF SCI & TECH
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