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Fluorescent probe for detecting fluorine ions and preparation method and application thereof

A fluorescent probe and fluoride ion technology, applied in the field of fluorescent probes, can solve the problems of complicated probe operation, high cost, difficult to identify anions, etc., and achieve the effect of good ultraviolet absorption performance

Pending Publication Date: 2020-07-17
SHANGHAI INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, people have designed and synthesized many anion fluorescent probes with potential application value, but most of the probes are complicated to operate, high in cost, and it is difficult to recognize anions under solid-state conditions.

Method used

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  • Fluorescent probe for detecting fluorine ions and preparation method and application thereof
  • Fluorescent probe for detecting fluorine ions and preparation method and application thereof
  • Fluorescent probe for detecting fluorine ions and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] The synthesis of fluorescent probe molecules for detecting fluoride ions in the present invention is obtained through a series of reactions using p-hydroxybenzaldehyde, pyrrole and tert-butyldiphenylchlorosilane as raw materials, including the following steps

[0060] (1) Synthesis of 4-(bis(1H-pyrrol-2 base)methyl)phenol:

[0061] p-Hydroxybenzaldehyde (5.00g, 40.94mmol), pyrrole (20mL, 289mmol) and anhydrous CH 2 Cl 2 (250 mL) was added into a 500 mL round-bottomed flask, nitrogen was replaced in the round-bottomed flask, and trifluoroacetic acid (200 mg, 2.60 mmol) was added to the mixture, and the reaction was stirred at room temperature for 3 h. After the reaction was complete, it was washed with saturated sodium bicarbonate solution. The organic layer was dried over anhydrous sodium sulfate, the filtrate was collected, concentrated by distillation under reduced pressure, and purified by silica gel column chromatography (petroleum ether: ethyl acetate = 3:1) to o...

Embodiment 2

[0110] A method for preparing a fluorescent probe for detecting fluoride ions, the method comprising the following steps:

[0111] (1) Synthesis of 4-(bis(1H-pyrrol-2 base)methyl)phenol:

[0112] In a dry nitrogen atmosphere, first stir and dissolve p-hydroxybenzaldehyde and pyrrole in the solvent anhydrous dichloromethane, and replace with nitrogen to form a mixture, then add trifluoroacetic acid to the mixture and react at room temperature for 2 hours; wait until the reaction is complete Afterwards, wash and dry, distill under reduced pressure, and collect after silica gel column chromatography to obtain brown solid 4-(bis(1H-pyrrol-2 base)methyl)phenol; wherein, p-hydroxybenzaldehyde, pyrrole, trifluoroacetic acid and no The molar volume ratio of dichloromethane in water is 40mmol: 280mmol: 2mmol: 250ml, and the developing solvent and volume ratio used for silica gel column chromatography purification are respectively petroleum ether: ethyl acetate=3:1;

[0113] (2) Synthe...

Embodiment 3

[0126] A method for preparing a fluorescent probe for detecting fluoride ions, the method comprising the following steps:

[0127] (1) Synthesis of 4-(bis(1H-pyrrol-2 base)methyl)phenol:

[0128]In a dry nitrogen atmosphere, first stir and dissolve p-hydroxybenzaldehyde and pyrrole in the solvent anhydrous dichloromethane, and replace with nitrogen to form a mixture, then add trifluoroacetic acid to the mixture and react at room temperature for 4 hours; wait until the reaction is complete Afterwards, wash and dry, distill under reduced pressure, and collect after silica gel column chromatography to obtain brown solid 4-(bis(1H-pyrrol-2 base)methyl)phenol; wherein, p-hydroxybenzaldehyde, pyrrole, trifluoroacetic acid and no The molar volume ratio of dichloromethane in water is 45mmol: 300mmol: 3mmol: 250ml, and the developing solvent and volume ratio used for silica gel column chromatography purification are respectively petroleum ether: ethyl acetate=3:1;

[0129] (2) Synthes...

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Abstract

The invention relates to a fluorescent probe for detecting fluorine ions and a preparation method and application of the fluorescent probe, the chemical name of the fluorescent probe is 8-(4-((4-((tert-butyldiphenylsilyl)oxy)phenyl)methoxy)phenyl)-dipyrromethene boron difluoride. The preparation method comprises (1) synthesis of 4-(di(1H-pyrrole-2-yl)methyl)phenol, (2) synthesis of p-hydroxyphenyl-dipyrromethene boron difluoride, and (3) synthesis of 8-(4-((4-((tert-butyldiphenylsilyl)oxy)phenyl)methoxy)phenyl)-dipyrromethene boron difluoride. The fluorescent probe is applied to detection of fluorine ions under a solid state condition. Compared with the prior art, the fluorescent probe has the advantages of good specificity, strong anti-interference capability, excellent sensitivity, low fluorescence detection limit, capability of detecting fluorine ions under a solid state condition and the like.

Description

technical field [0001] The invention relates to the field of fluorescent probes, in particular to a fluorescent probe for detecting fluoride ions and a preparation method and application thereof. Background technique [0002] Anions play an important role in chemistry, life science, medicine, environment and other fields, so the identification and detection of anions has important research and application value in these fields. In the field of biomedicine, a small amount of fluoride ions can promote the resistance of tooth enamel to bacterial acid corrosion and prevent tooth decay; while excessive intake of fluoride ions by the human body can cause dental fluorosis, skeletal fluorosis, uremia, etc., or even completely Lose the ability to work and take care of themselves. [0003] Early anion recognition methods were mainly realized through non-covalent weak interactions. In recent years, different types of anionic fluorescent probes have been constructed by combining anion...

Claims

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Application Information

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IPC IPC(8): C07F7/18C09K11/06G01N21/64
CPCC07F7/1804C07F7/188C09K11/06G01N21/643C09K2211/1014C09K2211/1055
Inventor 刘传祥陈曦付超李喆垚陈璐朱婷婷高晨
Owner SHANGHAI INSTITUTE OF TECHNOLOGY
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