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Substituted Rhodamine B acylthiosemicarbazide fluorescence probe compound and preparation method and application thereof

A technique for fluorescent probes and hydrazide compounds is applied in the field of substituted rhodamine B amidothiourea fluorescent probe compounds and their preparation, and can solve the problems of high requirements for instruments and equipment, high price, and no continuous detection allowed. Achieve good anti-interference ability, good selectivity and good sensitivity

Active Publication Date: 2016-11-16
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Traditional mercury ion determination methods include: ultraviolet spectrophotometry, atomic absorption / emission method, biosensor method, inductively coupled plasma mass spectrometry, and electrochemical method. Mercury content detection, but they have high requirements on the equipment of the instrument, are expensive, and require a large number of samples to be tested, and do not allow continuous detection. The limitations of these methods restrict the use of various samples to be tested, especially in vivo point-of-care detection and trace analysis

Method used

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  • Substituted Rhodamine B acylthiosemicarbazide fluorescence probe compound and preparation method and application thereof
  • Substituted Rhodamine B acylthiosemicarbazide fluorescence probe compound and preparation method and application thereof
  • Substituted Rhodamine B acylthiosemicarbazide fluorescence probe compound and preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0032] Synthesis of rhodamine B hydrazide compound

[0033] Take 1.443 g (3 mmol) of Rhodamine B and transfer it into a 100 mL round bottom flask, dissolve it with 50 mL of ethanol, then pipette 3 mL (80 wt%, 20 mmol) of hydrazine hydrate aqueous solution with a pipette gun, and the reaction system is now Dark wine red, reflux reaction in an oil bath at 85°C, monitor the progress of the reaction by thin-layer chromatography (TLC), the developer is a mixed solution of petroleum ether and ethyl acetate with a volume ratio of 1:1, and spot the plate after 6 hours of reaction It was found that the raw material spots basically disappeared on the thin-layer plate, and the rhodamine hydrazide product spots appeared at the position of about 0.5 in the ratio shift value. After the reaction was quenched, the system was extracted with ethyl acetate, and the organic phase was collected and then distilled under reduced pressure to obtain 1.2537 g of rhodamine hydrazide compound, with a yie...

Embodiment 2

[0035] Synthesis of o-chlororhodamine probe RBS1

[0036] Take 0.1260 g (0.75 mmol) of 2-chlorophenylisothiocyanate and 0.2292 g (0.5 mmol) of rhodamine hydrazide compound and transfer them to a 25 mL round-bottomed flask, then add 5 mL of dry isopropanol to Magnetically stir the reflux reaction in an oil bath at 85°C, and monitor the reaction by TLC after reacting for 5 minutes. The developer is a mixed solution of petroleum ether and ethyl acetate with a volume ratio of 1:1. After 10 hours, the raw material point disappears, and the reaction is stopped. , after the system was lowered to room temperature, the solvent was distilled off under reduced pressure and neutral alumina was added to its dry-mixed sample, and neutral alumina was used as the stationary phase for column chromatography (petroleum ether: ethyl acetate=10:2, v / v) Separation and purification, the product is white fluffy powder ortho-chlororhodamine probe RBS1 (yield 80%).

Embodiment 3

[0038] Synthesis of o-methoxyrhodamine probe RBS2

[0039] Take 0.1238 g (0.75 mmol) of 2-methoxyphenylisothiocyanate and 0.2292 g (0.5 mmol) of rhodamine hydrazide compound and transfer to a 25 mL round bottom flask, then add 5 mL of dry isopropanol , magnetically stirred and refluxed in an oil bath at 85°C. After 5 minutes of reaction, TLC was used to monitor the reaction. The developer was a mixed solution of petroleum ether and ethyl acetate with a volume ratio of 1:1. After 10 hours, the raw material point disappeared. After the reaction was stopped and the system was lowered to room temperature, the solvent was distilled off under reduced pressure and neutral alumina was added to dry mix the sample, and neutral alumina was used as the stationary phase for column chromatography (petroleum ether: ethyl acetate=10:2 , v / v) separation and purification, the product is white fluffy powder o-methoxyrhodamine probe RBS2 (yield 82%).

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Abstract

The invention discloses a substituted Rhodamine B acylthiosemicarbazide fluorescence probe compound and a preparation method and application thereof, and belongs to the technical field of synthesis of fluorescence probe compounds. According to the technical scheme, the substituted Rhodamine B acylthiosemicarbazide fluorescence probe compound has a chemical structural formula (please see the formula in the description), wherein R is Cl or OMe or CF3. The invention further discloses the preparation method of the substituted Rhodamine B acylthiosemicarbazide fluorescence probe compound and application of the substituted Rhodamine B acylthiosemicarbazide fluorescence probe compound serving as an organic molecular fluorescence probe for detecting heavy metal mercury ions. The fluorescence probe compound shows the good antijamming capability, can accurately detect a trace quantity of heavy metal mercury ions and is good in selectivity and sensitivity.

Description

technical field [0001] The invention belongs to the technical field of synthesis of fluorescent probe compounds, and in particular relates to a fluorescent probe compound substituted with rhodamine B amidothiourea and its preparation method and application. Background technique [0002] Mercury is a heavy metal, commonly known as mercury. Hg in ionic form 2+ It has high chemical activity and is one of the main heavy metal ions that cause environmental pollution. It shows strong physiological toxicity to organisms at very low concentrations. The harm of inorganic mercury to humans is mainly in the kidneys, while the methylmercury produced by the transformation of microorganisms in the environment will cause a variety of cardiovascular and cerebrovascular diseases to humans, and both forms of mercury will be bioaccumulated The effect is finally transferred to the human body, and mercury cannot be excreted from the body through its own metabolism, which seriously endangers hu...

Claims

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Application Information

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IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC07D491/107C09K11/06C09K2211/1029C09K2211/1088G01N21/6428
Inventor 时蕾鹿泽华刘统信麻娜娜张贵生刘青锋
Owner HENAN NORMAL UNIV
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