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A kind of xanthene dye butyl isothiocyanate derivative and its pdms sponge structure chip, preparation method and application

A technology of butyl isothiocyanate and structural chips, which is applied in the field of fluorescent sensing and detection technology and new functional materials, can solve the problems of lack of fluorescent probes for detecting heavy metals in the environment, and achieve the effect of excellent flexibility and good adsorption

Active Publication Date: 2021-01-29
SHANGHAI INST OF MICROSYSTEM & INFORMATION TECH CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The purpose of the present invention is to provide a xanthene dye butyl isothiocyanate derivative and its PDMS sponge structure chip, preparation method and application, thereby solving the problem of lack of effective fluorescent probes for detecting environmental heavy metals in the prior art

Method used

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  • A kind of xanthene dye butyl isothiocyanate derivative and its pdms sponge structure chip, preparation method and application
  • A kind of xanthene dye butyl isothiocyanate derivative and its pdms sponge structure chip, preparation method and application
  • A kind of xanthene dye butyl isothiocyanate derivative and its pdms sponge structure chip, preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Embodiment 1, preparation of xanthene fluorescent dye molecular probe

[0038] The specific method is as follows:

[0039] The xanthene fluorescent dye molecular probe is 3-hydroxyl-6-diethylamino-9-oxospiroisobenzofuran-xanthene, and the preparation steps are as follows:

[0040] 1) Add 2-(4-diethylamino-2-hydroxybenzoyl)benzoic acid (313mg, 1mmol) and resorcinol (110mg, 1mmol) into methanesulfonic acid (5mL) and stir evenly, and heat in the dark, Oil bath temperature 90°C, react for 24 hours;

[0041] 2) The above reaction solution was cooled to room temperature, poured into 80 mL of ice water and stirred, and the pH of the reaction solution was adjusted to neutral with 1.0 M aqueous sodium hydroxide solution. Then, the mixed solution was extracted several times with dichloromethane (50 mL). The collected organic phase was dried with anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain a crude product, which was separated ...

Embodiment 2

[0043] Embodiment 2, the preparation of xanthene dye hydrazine hydrate derivative

[0044] Proceed as follows:

[0045] 1) Add 3-hydroxy-6-diethylamino-9-oxospiroisobenzofuran-xanthene (186mg, 0.6mmol) and 80% hydrazine hydrate (1.5mL) obtained in Example 1 above to anhydrous In ethanol (20mL), heat under reflux in the dark, at an oil bath temperature of 95°C, and heat under reflux for 24 hours;

[0046] 2) Cool the above reaction solution to room temperature, pour it into 100 mL deionized water and stir. The mixed solution was extracted with dichloromethane (50 mL). The collected organic phase was dried with anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain a crude product, which was separated and purified by column chromatography on silica gel, and the eluent was dichloromethane and methanol (100:1). The target product xanthene dye hydrazine hydrate derivative was obtained as a white solid (144 mg) with a yield of 60%. Its H ...

Embodiment 3

[0048] Embodiment 3, preparation of xanthene dye butyl isothiocyanate derivative

[0049] Proceed as follows:

[0050] 1) Add the xanthene dye hydrazine hydrate derivative (100 mg, 0.25 mmol) and butyl isothiocyanate (150 μL, 1.25 mmol) obtained in the above Example 2 into N,N-dimethylformamide (DMF, 5mL), under nitrogen protection, stirred at room temperature for 28 hours;

[0051] 2) Pour the above reaction solution into 50 mL deionized water and stir. The mixed solution was extracted several times with dichloromethane (50 mL). The collected organic phase was dried with anhydrous magnesium sulfate, and distilled under reduced pressure to obtain a crude product, which was separated and purified by column chromatography on silica gel, and the eluent was dichloromethane and methanol (100:1). The pure target xanthene dye butyl isothiocyanate derivative was obtained as a pink solid (77 mg) with a yield of 60%. Its H NMR spectrum is as follows:

[0052] 1 H NMR (400MHz, DMSO...

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Abstract

The invention provides a xanthene dye butyl isothiocyanate derivative and its preparation method and application, and the xanthene dye butyl isothiocyanate derivative is 1‑(1‑(3‑hydroxy‑7 ‑diethylamino‑xanthene‑9yl)‑3‑oxo‑1,3‑dihydro‑isoindol‑2‑yl)‑3‑butyl‑thiourea. The invention also provides a PDMS sponge structure chip loaded with xanthene dye butyl isothiocyanate derivative, its preparation method and application. Novel xanthene dye butyl isothiocyanate derivative provided according to the invention, to Hg 2+ Fast response, high selectivity, high detection sensitivity, detection limit can reach 1×10 ‑7 M, and the preparation method is simple and easy, and the cost is low; and the PDMS sponge structure chip loaded with xanthene dye butyl isothiocyanate derivatives can be used to detect Hg 2+ , due to the simple structure and good detection effect of this type of chip, its application is more extensive, and it is expected to realize portable detection and provide a platform for fluorescent probes to be used in the detection of heavy metals and environmental pollutants.

Description

technical field [0001] The present invention relates to the technical field of fluorescence sensing detection technology and novel functional materials, more specifically to a xanthene dye butyl isothiocyanate derivative and its preparation method and application, and a xanthene dye-loaded isothiocyanate derivative PDMS sponge structure chip of butyl cyanate derivative and its preparation method and application. Background technique [0002] Heavy metal pollution not only has a huge impact on the environment, but also finally enters the top of the biological chain through the food chain. Due to the characteristics that heavy metals cannot be excreted in organisms, various diseases will inevitably form after a large amount of accumulation, such as mercury ions. Minamata disease can also damage the human nervous system and so on. At the same time, heavy metal pollution has become one of the important causes of water quality and soil pollution. At present, the methods used for...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B57/00G01N21/64
Inventor 梁丽娟班业伟赵建龙
Owner SHANGHAI INST OF MICROSYSTEM & INFORMATION TECH CHINESE ACAD OF SCI
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