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Fluorescent probe as well as preparation method and application thereof

A fluorescent probe and reaction technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of low probe detection sensitivity, high cost, complex synthesis route, etc., and achieve simple synthesis and fewer synthesis steps. , the effect of high sensitivity

Inactive Publication Date: 2015-02-18
SHANGHAI UNIVERSITY OF ELECTRIC POWER
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In view of the above-mentioned technical problems in the prior art, the present invention provides a fluorescent probe and its preparation method and application. Technical problems of low sensitivity, complex synthetic route and high cost

Method used

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  • Fluorescent probe as well as preparation method and application thereof
  • Fluorescent probe as well as preparation method and application thereof
  • Fluorescent probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Embodiment 1 (synthesis of probe):

[0044] (1) compound IV-1 Synthesis

[0045]

[0046] In a 50 mL Shrek tube, add the compound III-1 (469 mg, 1.0 mmol), under the protection of argon, inject dry tetrahydrofuran (20 mL), stir at -78 ℃, inject n-butyl lithium in n-hexane solution (2.5 mol?L -1 , 0.96 mL, 2.4 mmol). After stirring for 1 hour, a solution of N-formylmorpholine (344 mg, 3.0 mmol) and tetrahydrofuran (5 mL) was injected. After reacting for 1 hour, it was slowly raised to room temperature, and stirred for 12 hours. Add dilute hydrochloric acid (10 mL, 1 mol?L -1 ) acidified and stirred for 45 minutes. The layers were separated, the organic phase was separated, the aqueous phase was extracted with dichloromethane (20 mL×3), the organic phases were combined, and washed with saturated brine (20 mL). The organic phase was dried with anhydrous sodium sulfate, filtered with suction, the filter cake was washed with dichloromethane (20 mL×2), the filtrat...

Embodiment 2

[0052] Embodiment 2 (probe PTZ Fluorescent detection of cyanide ion):

[0053] Dissolve the molecular probe obtained above in a mixed solution of dimethyl sulfoxide-water (volume ratio 9:1), and configure it to 10 μmol?L -1 probe solution. Add 2.5 mL of the probe solution into a 1 cm×1 cm×4 cm stoppered cuvette, and then use a microsyringe to add different concentrations of CN - (sodium salt) after mixing evenly for 2 minutes, test its fluorescence emission spectrum, λ ex = 488 nm, the result is as figure 2 shown. With CN - The red fluorescence of the solution was gradually quenched by the continuous addition of . PTZ to CN - The detection limit is 67 nmol?L -1 , indicating that the probe pair CN - Has high detection sensitivity.

[0054] image 3 expressed in PTZ The concentration is 10 μmol?L -1 Under the condition of the dimethyl sulfoxide-water mixed solution (volume ratio of 9:1), the fluorescence intensity value F of the working solution at 702 nm and the...

Embodiment 3

[0055] Embodiment 3 (probe PTZ to CN - optional):

[0056] Dissolve the molecular probe obtained above in a mixed solution of dimethyl sulfoxide-water (volume ratio 9:1), and configure it to 10 μmol?L -1 probe solution. Add 2.5 mL of probe solution to a 1 cm×1 cm×4 cm stoppered cuvette each time, and then add 22 μmol?L with a microsyringe -1 CN - (sodium salt) and 200 μmol?L -1 Common anions (sodium or potassium salts), such as: F - , Cl - , Br - , I - , NO 2 - , NO 3 - , OAc - , PO 4 3- , HPO 4 2- , H 2 PO 4 - , HCO 3 - , CO 3 2- , SCN - , S 2- , SO 4 - . After uniform mixing for 2 minutes, test its fluorescence emission spectrum, λ ex = 488nm. The fluorescence intensity quenching ratio (I 0 -I) / I 0 (I and I 0 Indicates whether there is an anion or not PTZ The value of the fluorescence intensity at 702 nm) is plotted on the ordinate, and the results are as follows Figure 4 shown. Figure 4 show PTZ to CN - With good selectivity, th...

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Abstract

The invention provides a fluorescent probe. The structural formula of the fluorescent probe is represented by general formula I shown in the specification, wherein R is one of C7-C12 alkyl groups. The invention further provides a preparation method of the fluorescent probe and an application of the fluorescent probe to detection of cyanide ions. A phenothiazine derivative is used as a fluorescent parent, a malononitrile structure is introduced as an active center reacting with the cyanide ions, and selective detection of the cyanide ions is realized by the aid of fluorescent differences between reactants and products. The prepared fluorescent probe PTZ is excited at 488 nm and emitted at 702 nm, has very high selectivity and sensitivity for the cyanide ions and is high in response speed, the lowest concentration of the cyanide ions is detected to be 67 nmol / L<-1>, the cyanide ions can be detected quantitatively, and the fluorescent probe can be applied to detection of the cyanide ions in water bodies, soil and organisms.

Description

technical field [0001] The invention belongs to the field of chemical engineering, and in particular relates to a fluorescent probe, specifically a fluorescent probe, a preparation method thereof and an application in detecting cyanide ions. Background technique [0002] Cyanide is a fearsome and highly toxic substance that has been of human concern for over a hundred years and is still held in high regard today. After cyanide enters the organism, it decomposes into toxic cyanide ion (CN - ), cyanide ions can seriously affect many physiological organs and functions of the human body, such as vision, heart, central nervous system, blood vessels, endocrine, and metabolic systems. The most well-known is that cyanide ions can combine with iron ions in heme protein, thereby inhibiting the respiration of animals. In addition, cyanide ions also inhibit the activity of 42 enzymes in tissue cells. Although cyanide is highly toxic, it is still widely used in metallurgy, electroplat...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D279/22G01N21/64
Inventor 邹祺瞿祎郭颖慧
Owner SHANGHAI UNIVERSITY OF ELECTRIC POWER
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