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A colorimetric fluorescent probe compound for detecting fluoride ion and its detection method

A technology of fluorescent probes and compounds, applied in the field of analytical chemistry, to achieve the effects of strong fluorescence quenching, good selectivity, and obvious color changes

Active Publication Date: 2022-08-02
SHANDONG JIANZHU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In order to further improve the optical and electronic properties of PTACs, the development of PTAC derivatives with extended positions has received great attention in the past few years. Extended positions can lead to aromatic systems with planar structures and conjugated large π bonds. The conformation facilitates the transfer of electrons from the electron donor (F - Efficient intramolecular charge transfer (ICT) to the electron acceptor (bay position extended PTAC), five-membered or six-membered heterocyclic PTAC fluorescent probes containing heteroatoms such as S-, O- and N- in the perylene skeleton needles have been reported, however, PTAC probes containing a seven-atom ring at the perylene bay position have not been reported

Method used

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  • A colorimetric fluorescent probe compound for detecting fluoride ion and its detection method
  • A colorimetric fluorescent probe compound for detecting fluoride ion and its detection method
  • A colorimetric fluorescent probe compound for detecting fluoride ion and its detection method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Example 1. Preparation of colorimetric fluorescent probes

[0017] The synthetic route is shown in the following formula:

[0018]

[0019] Compound 3 (1.0 g, 1.44 mmol), zinc powder (0.5 g, 8.0 mmol), ammonium chloride (0.8 mg, 16.0 mmol) were dissolved in 100 mL of tetrahydrofuran. The mixture was stirred at room temperature for 3 h, and the ammonium chloride and zinc dust were removed by filtration. The crude product of the filtrate was purified by silica gel column chromatography to obtain compound 2 (0.76 g, 80%) as a dark brown solid. Compound 2 (0.4 g, 5.0 mmol) and formic acid catalyzed by paraformaldehyde (0.12 g, 4.0 mmol) were dissolved in 100 mL of ethanol and heated under reflux for 12 h. The precipitate was collected by filtration, and the crude product was purified by silica gel column chromatography (dichloromethane: ethyl acetate, 2%) to obtain the colorimetric fluorescent probe P1 of the present invention (0.25 g, 62%, M.p.: 300-302°C). 1H NMR (4...

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Abstract

The invention discloses a colorimetric fluorescent probe compound for detecting fluoride ions and a detection method thereof, belonging to the technical field of analytical chemistry. The colorimetric fluorescent probe structure is a perylene tetracarboxylate with a seven-atom ring containing N-H and O at the perylene bay position. The colorimetric fluorescent probe of the present invention has good solubility and fluorescence performance in organic solvents, and has good solubility in F ‑ The absorption peak is red-shifted in the presence of ions, showing obvious color change and strong fluorescence quenching; good selectivity, chloride ion, bromide ion, iodide ion, sulfate, acetate, perchlorate and dihydrogen phosphate to fluorine There is no obvious interference in the determination of ion concentration, and it can be used as a colorimetric and fluorescent probe for fluoride ion detection.

Description

technical field [0001] The invention belongs to the technical field of analytical chemistry, and relates to a method for detecting fluoride ions (F - ) colorimetric fluorescent probe compounds and their detection methods. Background technique [0002] The construction of organic molecular sensing probes with high selectivity and high sensitivity capable of anion recognition is a research hotspot in supramolecular chemistry. Among various types of anions, F - plays important roles in different environmental, biological and industrial processes, small amounts of F - It is important for preventing enamel demineralization and caries caused by the use of orthodontic appliances, and it is also used to treat osteoporosis. However, a large number of F - It can lead to fluorosis, urolithiasis, nephrotoxic changes and even cancer. The U.S. Environmental Protection Agency (EPA, USA) recommends F in water - The allowable concentration is 2ppm. Therefore, colorimetric and fluoresc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D267/06C09K11/06G01N21/64
CPCC07D267/06C09K11/06G01N21/643C09K2211/1033G01N2021/6432
Inventor 马永山夏延钊张凤霞
Owner SHANDONG JIANZHU UNIV
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