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Ratio type near-infrared fluorescent probe for detecting sulfur dioxide derivatives and preparation method thereof

A technology of sulfur dioxide and fluorescent probe, applied in the field of fluorescence detection

Inactive Publication Date: 2020-10-27
JIANGSU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

(1) The probe must be on the SO 2 Derivatives Show Ratiometric Fluorescence Responses

Method used

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  • Ratio type near-infrared fluorescent probe for detecting sulfur dioxide derivatives and preparation method thereof
  • Ratio type near-infrared fluorescent probe for detecting sulfur dioxide derivatives and preparation method thereof
  • Ratio type near-infrared fluorescent probe for detecting sulfur dioxide derivatives and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Synthesis of fluorescent probes.

[0044] The preparation steps are summarized as:

[0045] Step 1. Dissolve m-diethylaminophenol in concentrated hydrochloric acid and water to prepare a mixed solution, then dissolve sodium nitrite in water, and drop into the above mixed solution in an ice bath. After further stirring, the resulting yellow solid was collected by filtration and washed with saturated sodium acetate solution. Then recrystallize to obtain red needle-like crystals;

[0046] Step 2, adding the intermediate product obtained in step 1 to ethanol. The resulting mixture was added with 85% hydrazine hydrate, and then a palladium carbon catalyst was added to the mixture under a nitrogen atmosphere, and the mixture was stirred under reflux until the red color of the solution disappeared. To avoid oxidative degradation, the obtained compound 2 was used directly in the next step without purification step.

[0047] Step 3, adding ethyl pyruvate to the solution obta...

Embodiment 2

[0057] The fluorescent probe that embodiment 1 obtains is to HSO 3 - Selectivity of fluorescence detection.

[0058] Concentrate 5×10 in DMF -4 M fluorescent probe molecular mother solution, ready to use. Prepare a concentration of 1×10 with deionized water -3 M's HSO 3 - (2), SO 3 2- (3), S 2 o 3 2- (4),HS - (5), HSO 4 - (6), SO 4 2- (7),Na + (8),Mg 2+ (9),F - (10), Cl - (11), NO 2 - (12),ACO - (13), NO 3 - (14), Cys(15), Hcy(16), and GSH(17) solutions, wherein (1) is a blank solution, when various analyte solutions are added to the test solution of 5 μM fluorescent probe molecules, at 421nm As the excitation wavelength, the fluorescence spectrum is measured, and the response of the probe molecule to different analytes is detected. The measurement results are as follows: figure 2 shown.

[0059] from figure 2 The results can be found that only HSO 3 - and SO 3 2- The fluorescence of the fluorescent probe can be significantly enhanced, and the ...

Embodiment 3

[0061] Other common ions or molecules interfere with the detection of hydrogen sulfide by the fluorescent probe obtained in Example 1.

[0062] like image 3 Among them, prepare the test solution according to Example 2, first add 533 μM of other possible interfering substances to the 5 μM fluorescent probe molecule test solution, including S 2 o 3 2- (2),HS - (3),HSO 4 - (4), SO 4 2- (5),Na + (6),Mg 2+ (7), F - (8), Cl - (9), NO 2 - (10),ACO - (11), NO 3 - (12), Cys(13), Hcy(14), and GSH(15), wherein (1) is a blank solution with only sodium bisulfite, and then add 533 μM sodium bisulfite (providing HSO 3 - ). After mixing for 10 minutes, under the same conditions, the excitation wavelength of 421nm was used to perform the fluorescence spectrum test to obtain the fluorescence spectrum of each group of solutions.

[0063] from image 3 It can be found in the results that when the system is added with S 2 o 3 2- ,HS - , HSO 4 - , SO 4 2- , Na + ,Mg 2...

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Abstract

The invention belongs to the technical field of fluorescence detection, and particularly relates to a ratio type near-infrared fluorescent probe for detecting sulfur dioxide (SO2) derivatives, a preparation method and application thereof to detection of SO2 derivatives in crop leaf tissues, SO2 derivatives in atmosphere or SO2 derivatives in soil. M-diethylaminophenol, sodium nitrite, hydrazine hydrate, a palladium-carbon catalyst, ethyl pyruvate, selenium dioxide, 1-ethyl-2-methylquinoline and the like are adopted as the raw materials to prepare the ratio type near-infrared fluorescent probefor detecting the sulfur dioxide derivative, and the fluorescent probe is used for detecting SO2 derivatives in the atmosphere, SO2 derivatives in the soil or SO2 derivatives in crop leaf tissues. Thefluorescent probe is simple in synthesis method, good in SO2 derivative selectivity and high in sensitivity, and the detection environment is suitable for large-range pH. An attempted probe test paper is a simple and portable tool, and can realize rapid on-site detection of sulfur dioxide derivatives in the atmosphere without depending on large-scale instruments and equipment, so that the attempted probe test paper has innovative significance.

Description

technical field [0001] The invention belongs to the technical field of fluorescence detection, in particular to a method for detecting sulfur dioxide (SO 2 ) derivative ratio near-infrared fluorescent probe and preparation method thereof, and in detecting SO in crop leaf tissue 2 Derivatives, SO in the atmosphere 2 Derivatives or SO in soil 2 applications of derivatives. Background technique [0002] Sulfur is a macronutrient for crops and is commonly found in amino acids (Cys, Hcy and Met), proteins and many metabolites. Sulfur nutrients are critical to the yield and quality of crops. There is ample evidence that sulfur dioxide (SO 2 ) is an important source of sulfur nutrients. In general, crop leaves can absorb SO through open stomata 2 . SO 2 Enter the crops, dissolve in the cytoplasm, and hydrolyze to generate its derivative sulfite (SO 3 2- ) and bisulfite (HSO 3 - ), and then further reduced to sulfide, combined to generate cysteine, and then synthesized ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/06C09K11/06G01N21/64
CPCC07D413/06C09K11/06G01N21/6458G01N21/643C09K2211/1029C09K2211/1033
Inventor 龙凌亮陈倩刘卫国韩园园袁芳李璐璐王坤
Owner JIANGSU UNIV
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