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Fluorescent molecular probe for detecting sulfite ions through naked eyes and fluorescence ratio as well as synthesis and application thereof

A fluorescent molecular probe and sulfite technology, which is applied in the directions of fluorescence/phosphorescence, color/spectral characteristic measurement, luminescent materials, etc., can solve the problems of fluorescence intensity enhancement and limited application, and achieve high synthesis yield and wide detection range , the effect of low detection limit

Inactive Publication Date: 2014-09-10
CENT SOUTH UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, most of these probe design principles are based on the enhancement or weakening of fluorescence intensity, which is largely affected by the probe concentration, excitation light intensity and environment, which greatly limits its application.
However, sulfite fluorescent probes designed based on the principle of naked-eye detection and fluorescence ratio wavelength are rarely reported.

Method used

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  • Fluorescent molecular probe for detecting sulfite ions through naked eyes and fluorescence ratio as well as synthesis and application thereof
  • Fluorescent molecular probe for detecting sulfite ions through naked eyes and fluorescence ratio as well as synthesis and application thereof
  • Fluorescent molecular probe for detecting sulfite ions through naked eyes and fluorescence ratio as well as synthesis and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1: Preparation of Molecular Fluorescent Probe 1

[0031] 269mg (1mmol) of 4-hydroxynaphthalimide, 309mg (1.5mmol) of 1,3-dicyclohexylcarbodiimide (DCC), 73mg (0.6mmol) of 4-dimethylaminopyridine, 150mg (1.3 mmol) was added into 30 mL of dichloromethane, and refluxed for 4 hours. Then the temperature was lowered, and 20 mL of water was added to quench the reaction. Extracted three times with dichloromethane and washed with saturated sodium chloride. It was dried over anhydrous sodium sulfate and separated by column chromatography to obtain 165 mg (45%) of the probe compound as a white solid 1 .

[0032] 1 H NMR (400MHz, CDCl 3 ): δppm = 8.64-8.59 (m, 2H), 8.37 (d, J = 8.8Hz, 1H), 7.81 (t, J = 7.6Hz, 1H), 7.52 (d, J = 8.0Hz, 1H), 4.18 (t, J=7.6Hz, 2H), 3.03-3.01(m, 2H), 2.99-2.97(m, 2H), 2.27(s, 3H), 1.71(s, 2H), 1.44(d, J=7.6 Hz, 2H), 0.98(t, J=7.6Hz, 3H)

Embodiment 2

[0033] Example 2: Preparation of Molecular Fluorescent Probe 1

[0034] 269mg (1mmol) of 4-hydroxynaphthalimide, 131mg (1.3mmol) of triethylamine, 73mg (0.6mmol) of 4-dimethylaminopyridine, and 175mg (1.3mmol) of levulinyl chloride were added to 30mL of dichloromethane, room temperature Stir for 4 hours. Then the temperature was lowered, and 20 mL of water was added to quench the reaction. Extracted three times with dichloromethane and washed with saturated sodium chloride. It was dried over anhydrous sodium sulfate and separated by column chromatography to obtain 158 mg (43%) of the probe compound as a white solid 1.

[0035] 1 H NMR (400MHz, CDCl 3 ): δppm = 8.64-8.59 (m, 2H), 8.37 (d, J = 8.8Hz, 1H), 7.81 (t, J = 7.6Hz, 1H), 7.52 (d, J = 8.0Hz, 1H), 4.18 (t, J=7.6Hz, 2H), 3.03-3.01(m, 2H), 2.99-2.97(m, 2H), 2.27(s, 3H), 1.71(s, 2H), 1.44(d, J=7.6 Hz, 2H), 0.98(t, J=7.6Hz, 3H)

Embodiment 3

[0036] Embodiment 3: The application of naked eye and fluorescence ratio detection sulfite ion fluorescent probe

[0037] The probe was dissolved in acetonitrile solution, and the corresponding anion buffer was added to prepare 10×10 -6 M (acetonitrile: HEPES buffer = 1: 1) solution, test its ultraviolet absorption spectrum and fluorescence spectrum changes. Figure 1-Figure 11 It shows that the probe has high selectivity to sulfite ions in the ultraviolet spectrum and fluorescence spectrum. With the increase of the concentration of sulfite added, the ultraviolet spectrum and fluorescence spectrum are obviously red-shifted, and the color of the solution changes. The color change is also suitable for naked eye detection, while the fluorescence changes from blue to yellow. And the probe is not affected by F - , Cl - , Br - , I - , HPO 4 2- , SO 4 2- , NO 3 - , AcO - , ClO 4 - , N 3 - , HCO 3 - The influence of other anions. The probe responds well to sulfite io...

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PUM

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Abstract

The invention relates to a preparation method of a fluorescent molecular probe for detecting sulfite ions through naked eyes and fluorescence ratio as well as the application of the fluorescent molecular probe in detecting sulfite ions. The fluorescent molecular probe is prepared by condensing 4-hydroxy naphthalimide serving as raw material and acetylpropionic acid in refluent methylene dichloride. The synthesis is simple and convenient, and the reaction conditions are mild. The probe molecule provided by the invention has higher sensitivity, stable fluorescence performance, higher synthesis yield and good selectivity, and furthermore, the response range of the probe is 0-1500 mu m, the detection limit is 6 mu m; the detection range is wide, the lower detection limit is low, and the probe is suitable for naked eye detection. Meanwhile, the florescence-ratio detection is adopted to avoid errors caused by exciting light intensity, probe concentration and environment factors of an off-on type probe which detects ions only depending on the change of fluorescence intensity and the probe disclosed by the invention is not influenced by anions such as F<->, Cl<->, Br<->, I<->, HPO4<2->, SO4<2->, NO<3->, AcO<->, ClO<4->, N<3-> and HCO<3->. Even interfering ions exist, the probe has very good response to sulfite ions. Therefore, the fluorescent molecular probe has practical application value in the fields of biochemistry, environmental science 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 detecting sulfite ions with the naked eye and fluorescence ratio and the application of the fluorescent molecular probe in detecting sulfite ions. Background technique [0002] In the past few decades, sulfite, as an important additive, has been widely used in environmental industry and food chemistry. Sulphite lye has been used in the paper industry since 1867 to produce sulphite cellulose. In many food and beverage products, sulfites are used as preservatives to resist oxidation and inhibit bacterial growth, thereby controlling the occurrence of enzymatic or non-enzymatic reactions during production and storage. However, sulfite in industry and food has a double effect, it is not only an important element, but also a toxic substance, and this potential toxicity cannot be ignored. Sulphite wastewa...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D221/14C09K11/06G01N21/64G01N21/29
Inventor 宋相志陈颂
Owner CENT SOUTH UNIV
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