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A kind of fluorescent probe and its preparation method and application

A technology of fluorescent probes and compounds, applied in the field of fluorescent probe detection, can solve the problems of large ionic radius of iodide, low hydrogen bonding ability, low charge density, etc., and achieve the effects of strong selectivity, easy operation and high sensitivity

Active Publication Date: 2020-06-30
GUIZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The design of common iodide ion probes is mostly based on the complexation of hydrogen bonds or coordination bonds. Currently, due to the large ionic radius, low charge density, and low hydrogen bonding ability of iodide ions, it is challenging to develop feasible iodide ion probes. , some of the existing iodide ion probes have insufficient specificity and are easily interfered by other anions; some have high cost and are difficult to synthesize

Method used

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  • A kind of fluorescent probe and its preparation method and application
  • A kind of fluorescent probe and its preparation method and application
  • A kind of fluorescent probe and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] A fluorescent probe, the molecular formula of the fluorescent probe is: C 90 h 81 N 3 o 9 ; The structural formula of the fluorescent probe is:

[0037]

[0038] This embodiment also provides a method for preparing the above-mentioned fluorescent probe, which method includes the following steps:

[0039]Step 1. Under the protection of nitrogen, add 500mg of compound A, 210mg of NaH and 25mL of dry tetrahydrofuran into a 50mL round bottom flask, heat and reflux at 100°C for 1 hour, add 780mg of N,N-diethyl -2-Chloroacetamide, continue to heat and reflux for 20 hours, distill off THF, add 20 mL of water to the refluxed product, adjust the pH to 7.0 with 1 mol / L hydrochloric acid solution, and then extract with 20 mL of ethyl acetate a 3 times, combined the organic phase a, washed the organic phase a 3 times with water, dried with anhydrous magnesium sulfate, and evaporated to dryness at a temperature of 100°C to obtain a yellow viscous substance, which was reconsti...

Embodiment 2

[0049] This embodiment provides the application of the fluorescent probe prepared in Example 1. The fluorescent probe is used to identify iodide ions, and the method for identifying iodide ions is:

[0050] Dissolve the fluorescent probe prepared in Example 1 in the blank stock solution, configure the fluorescent reagent with a concentration of 50 μmol / L of the fluorescent probe, pipette 2.4 mL of the blank stock solution into a quartz cuvette with a pipette gun, and then Add 300 μL fluorescent reagent and 300 μL aqueous solution with a concentration of 10 mmol / L to obtain a mixture solution with a fluorescent probe concentration of 5 μmol / L, perform fluorescence excitation at a wavelength of 346 nm, and identify iodide ions in the aqueous solution to be tested ;

[0051] The blank stock solution consists of tetrahydrofuran and 2 × 10 -3 The Tris-HCl buffer solution (trishydroxymethylaminomethane and hydrochloric acid mixture that the molar concentration ratio is 1:1) that th...

Embodiment 3

[0059] This embodiment is the anti-interference test when the fluorescent probe prepared in Example 1 is used to identify iodide ions:

[0060] Dissolve the fluorescent probe prepared in Example 1 in the blank stock solution, configure the fluorescent reagent with a concentration of 50 μmol / L of the fluorescent probe, pipette 2.1 mL of the blank stock solution into a quartz cuvette with a pipette gun, and then Add 300 μL of fluorescent reagent and 300 μL of iodide ion aqueous solution with a concentration of 10 mmol / L to obtain test solution A, and then add 300 μL of F with a concentration of 10 mmol / L to test solution A respectively. - Aqueous solution, Cl - Aqueous solution, Br - Aqueous solution, Aco - Aqueous solution, SO 3 2- Aqueous solution, SO 4 2- Aqueous solution, HSO 3 - Aqueous solution, NO 2 - aqueous solution and CO 3 2- Aqueous solution, obtain respectively test No. liquid B, test No. liquid C, test No. liquid, test No. E liquid, test No. F liquid, t...

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Abstract

The invention provides a fluorescent probe and a preparation method thereof. The fluorescent probe is obtained through a three-step reaction; N,N-diethyl-2-chloroacetamide is added after a compound A,Nah and tetrahydrofuran are heated, refluxed and cooled; a compound B is obtained by refluxing, extracting, drying and re-crystallizing; 1,4-dioxane and NaOH aqueous solution are added for refluxing,extracting, drying and re-crystallizing to obtain a compound C; 1-hydroxybenzotriazole, 1-aminopyrene and dichloromethane are added; a dichloromethane solution of dicyclohexylcarbodiimide is added dropwise in an ice bath; a reaction is performed at room temperature; column chromatography separation is performed to obtain the fluorescent probe. The invention also provides the application to identifying iodide ions. The synthesizing method provided by the invention is simple, easy to operate, less in reaction steps and high in yield; the fluorescent probe has strong selectivity on the iodide ions, is not easily interfered with other negative ions, and has real-time performance and high sensitivity; the iodine ions in an aqueous solution to be detected is detected instantaneously; the fluorescent probe has practical significance in detecting the content of the iodine ions in an ecological environment, and can meet the requirements of detection and quantification under low iodide concentration.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probe detection, and in particular relates to a fluorescent probe and its preparation method and application. Background technique [0002] Among the biologically important anions, iodine has attracted particular attention in recent years because it is an essential micronutrient that plays fundamental physiological roles at all stages of human development. At the same time, the important role of iodine in controlling the normal growth of the human body and maintaining the normal function of the thyroid gland has also received more and more attention. [0003] Iodine is an essential trace element for the human body. It often exists in the form of iodide in the human body. It plays a very important role in regulating cell metabolism, neuromuscular tissue development and growth, carbohydrate and lipid metabolism, etc. In addition, iodine is also widely used in the chemical synthesis of drugs and...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C07D323/00G01N21/64
CPCC07D323/00C09K11/06C09K2211/1011C09K2211/1088G01N21/643
Inventor 谢海芳徐红张奇龙黄亚励吴翀
Owner GUIZHOU MEDICAL UNIV