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Fluorescent molecular probe for detecting fluoride ions as well as synthesis method and application thereof

A fluorescent molecular probe and fluoride ion technology, applied in the field of chemical analysis and detection, can solve the problems of limiter application, limitation, fluorescence intensity quenching, etc., and achieve the effects of wide detection range, low detection lower limit and high synthesis yield

Inactive Publication Date: 2015-03-18
SUZHOU ROWLAND BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, data on the detection of fluoride ions by fluorescent probes are still quite limited, in particular, methods based on anion-induced fluorescence intensity quenching would greatly limit the application of

Method used

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  • Fluorescent molecular probe for detecting fluoride ions as well as synthesis method and application thereof
  • Fluorescent molecular probe for detecting fluoride ions as well as synthesis method and application thereof
  • Fluorescent molecular probe for detecting fluoride ions as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment 1: the preparation of compound 2

[0029] In a 100 mL single-neck round bottom flask, add 2-hydroxy-1-naphthaldehyde (172 mg, 1 mmol) and triethylamine (121 mg. 1.2 mmol) in 15 mL of dichloromethane, and stir at room temperature for 30 minutes. Tert-butyldimethylsilyl chloride (180 mg, 1.2 mmol) was added to the above reaction system, followed by stirring at room temperature for 2 hours. The reaction solution was poured into 100 mL of water to quench the reaction. It was extracted with 30 mL of dichloromethane, and the organic phase was separated and dried with anhydrous sodium sulfate, and the solvent was distilled off to obtain 237 mg of solid product (yield: 83 %), which was compound 2, which was directly carried out to the next step without purification.

Embodiment 2

[0030] Embodiment 2: Preparation of molecular fluorescent probe

[0031] In a 50 mL single-necked flask, compound 2 (29 mg, 0.1 mmol) and malononitrile (6.6 mg, 0.1 mmol) were dissolved in 10 mL of ethanol, 1 drop of piperidine was added, and reacted at room temperature for 30 minutes. The reaction solution was poured into water, extracted with dichloromethane, dried over anhydrous sodium sulfate, and separated by column chromatography (petroleum ether / ethyl acetate at a volume ratio of 50:1 as eluent) to obtain 14 mg of the product (yield: 42%) is the probe compound.

[0032] 1 H NMR (300 MHz, CDCl 3 ) δ 8.38 (s, 1H), 7.91 (d,J = 9.0 Hz, 1H), 7.84 (d, J = 8.1 Hz, 1H), 7.72 – 7.56 (m, 2H), 7.47 (t, J = 7.3 Hz, 1H), 7.14 (d, J = 9.0 Hz, 1H), 1.04 (s, 9H), 0.31 (s, 6H).

Embodiment 3

[0033] Example 3: Application of Naked Eye Recognition and Detection of Fluoride Ion Fluorescent Molecular Probes

[0034] The probe was dissolved in acetonitrile solution at a concentration of 25 μM, and different anions (25 μM of fluoride, dihydrogen phosphate, acetate, bromide, hydrogen sulfate, chlorate, iodide, chloride, Nitrate) solution to test its UV absorption spectrum; the probe was dissolved in acetonitrile solution at a concentration of 10 μM, and different anions (100 μM of fluoride ion, dihydrogen phosphate, acetate, bromide ion, hydrogen sulfate root, chlorate, iodide, chloride, nitrate) solution, test the change of fluorescence emission spectrum. Figure 1-Figure 7 It shows that fluorescent molecular probes have high sensitivity to fluoride ions in the ultraviolet absorption spectrum and fluorescence emission spectrum. After adding fluoride ions, the ultraviolet absorption spectrum is obviously red-shifted from 315 nm to 410 nm. When excited at 410 nm, the re...

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Abstract

The invention relates to a preparation method of a fluorescent molecular probe for detecting fluoride ions through colorimetric detection and fluorescence enhancement and an application of the fluorescent molecular probe to detecting fluoride ions. The fluorescent molecular probe is prepared by protecting 2-hydroxyl-1-naphthaldehyde taken as a raw material with silane and then condensing the raw material and malononitrile. The fluorescent molecular probe is simple and convenient to synthesize, and reaction conditions are mild. The fluorescent molecular probe has the specific characteristics that the probe molecule has stable optical properties and higher synthetic yield; the probe molecule has high fluoride ion detection sensitivity and low lower limit of detection, and the limit of detection is 0.52mu M; the response range is 0-100mu M and the detection range is wide; the probe molecule has good selectivity and has no responses to anions, such as dihydrogen phosphate radicals, acetate radicals, bromide ions, hydrosulfate radicals, chlorate radicals, iodide ions, chloride ions and nitrate radicals; the probe molecule is suitable for colorimetric detection; the fluorescent molecular probe has practical application values in the fields of biochemistry, environmental sciences and the like.

Description

technical field [0001] The invention relates to the technical field of chemical analysis and detection, in particular to a method for preparing a fluorescent molecular probe for naked-eye recognition and fluorescence enhanced detection of fluoride ions and the application of the fluorescent molecular probe in detecting fluorine ions. [0002] Background technique [0003] Anions are important elements to maintain biological life activities, and they exist in large quantities in biological systems. At the same time, anions are used in chemical reactions as nucleophiles, bases, redox agents, and phase transfer catalysts. In recent years, the design and synthesis of fluorescent sensors for the determination of anions has aroused great interest of researchers. Fluoride ions play an extremely important role in the prevention of dental diseases and the treatment of osteoporosis and other diseases; at the same time, its chemical properties are very active, and fluorine widely exis...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/18C09K11/06G01N21/64G01N21/78
Inventor 宋相志陈颂
Owner SUZHOU ROWLAND BIOTECH
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