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Fluorescent probe used for sulfite or bisulphate and preparation method and application thereof

A fluorescent probe and sulfurous acid technology, which is applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, and luminescent materials, can solve the problems of low sensitivity, short fluorescence emission wavelength, poor sensor selectivity, etc., and achieve high detection sensitivity and molecular structure. The effect of simple and convenient synthesis method

Inactive Publication Date: 2016-07-06
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

(3) If animals eat food containing sulfites for a long time, they will have adverse symptoms such as nerve inflammation and bone marrow atrophy, which will hinder the growth of animals
At present, there are few sulfite chemical sensors reported in the literature. These sensors have poor selectivity, low sensitivity, and short fluorescence emission wavelengths, which cannot avoid the interference of other substances in food or complex biological systems. There are almost no fluorescent probes that can be practically applied.

Method used

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  • Fluorescent probe used for sulfite or bisulphate and preparation method and application thereof
  • Fluorescent probe used for sulfite or bisulphate and preparation method and application thereof
  • Fluorescent probe used for sulfite or bisulphate and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] A kind of fluorescent probe that is used for sulfite (hydrogen) salt detection, chemical formula is C 29 h 29 N 2 f 4 I, and the molecule has the following structure:

[0029]

[0030] The preparation method steps are as follows:

[0031] Dissolve 1 millimole of benzindole quaternary ammonium salt in 20 milliliters of absolute ethanol, then add 1.2 millimoles of pentafluorobenzaldehyde, add 20 microliters of hexahydropyridine as a catalyst, react at 45 ° C for 4 hours, and concentrate the reaction solution Finally, fluorescent probe A was obtained as a dark red solid compound through silica gel column chromatography.

[0032] 1 HNMR (400MHz, d 6 -DMSO): δ(ppm)=8.45(d,1H),8.33(d,1H),8.24(d,1H,),8.19(d,1H),8.07(d,1H),7.82(t,1H ),7.75(t,1H),7.51(d,1H),4.75(q,2H,),3.41(s,4H),2.00(s,6H),1.65(s,6H),1.54(t,3H ). 13 CNMR (100MHz,d 6 -DMSO): δ (ppm) 182.0, 139.5, 138.6, 137.0, 133.9, 131.8, 130.5, 129.0, 128.0, 127.2, 123.7, 115.6, 113.8, 54.4, 52.2.52.2, 43.58, 26.6,...

Embodiment 2

[0037] A kind of fluorescent probe that is used for sulfite (hydrogen) salt detection, chemical formula is C 29 h 29 N 2 f 4 I, and the molecule has the following structure:

[0038]

[0039] The preparation method steps are as follows:

[0040] Dissolve 1 mmol of benzindole quaternary ammonium salt in 20 milliliters of absolute ethanol and toluene mixed solution (volume ratio is 1:1), then add 10 mmol of pentafluorobenzaldehyde, add 40 microliters of hexahydropyridine as Catalyst, reacted at 25°C for 10 hours, concentrated the reaction solution, and obtained dark red solid compound fluorescent probe A through silica gel column chromatography.

[0041] 1 HNMR (400MHz, d 6 -DMSO): δ(ppm)=8.45(d,1H),8.33(d,1H),8.24(d,1H,),8.19(d,1H),8.07(d,1H),7.82(t,1H ),7.75(t,1H),7.51(d,1H),4.75(q,2H,),3.41(s,4H),2.00(s,6H),1.65(s,6H),1.54(t,3H ). 13 CNMR (100MHz,d 6 -DMSO): δ (ppm) 182.0, 139.5, 138.6, 137.0, 133.9, 131.8, 130.5, 129.0, 128.0, 127.2, 123.7, 115.6, 113.8, 54.4, 5...

Embodiment 3

[0045] A kind of fluorescent probe that is used for sulfite (hydrogen) salt detection, chemical formula is C 31 h 33 N 2 o 2 I, and the molecule has the following structure:

[0046]

[0047] The preparation method steps are as follows:

[0048] Dissolve 1 mmol of benzindole quaternary ammonium salt in 15 ml of anhydrous acetonitrile, then add 2 mmol of coumarin aldehyde, without catalyst, react at 80°C for 4 hours, concentrate the reaction solution, pass through a silica gel column layer The purple solid compound fluorescent probe B was obtained by analysis.

[0049] 1 HNMR (400MHz, CDCl 3 ):δ7.96(m,1H),7.86(dd,1H),7.77(dd,1H),7.59(m,1H),7.53–7.42(m,2H),7.17(dd,1H),6.84( d,1H),6.61(dd,1H),6.43(d,J=2.1Hz,1H),6.25(d,1H),6.09(d,1H),3.34(m,4H),1.42(s,6H ),1.43–1.36(m,2H),1.30–1.23(m,3H),1.10(t,6H). 13 CNMR (100MHz, CDCl 3 ):δ173.95,161.82,160.32,154.63,141.97,141.00,139.69,139.07,133.09,131.21,129.70,129.57,129.20,128.37,128.19,124.42,119.32,113.99,113.64,110.71,109....

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Abstract

A class of fluorescent probes for the detection of sulfite (hydrogen) salts, consisting of benzoindole quaternary ammonium salts, and the molecule has the following structure: Wherein: R is a kind of in alkyl, aryl, nitro, ester group and ether group of 1-18 carbons independently or at the same time, or benzene, naphthalene, anthracene, pyrene, pyridine, pyrrole, indole, One of coumarin, fluorescein, carbazole, rhodamine, fluorene and quinoline and derivatives thereof; n is 0-20; X ‑ for F ‑ , Cl ‑ , Br ‑ or I ‑ , + is a positive charge. The advantages of the invention are: the fluorescent probe has good selectivity to sulfite, and the fluorescence intensity of the fluorescent probe solution and the concentration of sulfite are in the range of 0-8×10 ‑6 The linear relationship in the molar / liter range is good, showing good practical applicability; the fluorescent probe has a short response time, high detection sensitivity, simple molecular structure, and simple synthesis method, which makes it extremely easy for practical application.

Description

technical field [0001] The invention relates to a method for detecting (hydrogen) sulfite with high selectivity and high sensitivity, in particular to a fluorescent probe for detecting (hydrogen) sulfite and its preparation method and application. Background technique [0002] In recent years, with the improvement of people's living standards, food safety issues have attracted more and more attention. Food additives are the main cause of food problems. Among many food additives, sulfite is an important food antiseptic and preservative. Because sulfite has reducing properties, it can prevent oxidase from destroying food nutrients and changing color, and can inhibit microbial reproduction. Therefore, it has bleaching, antiseptic, and anti-oxidation functions. It can be used not only as a preservative for fruits and vegetables, but also as a Inhibitors to prevent food spoilage. [0003] However, too much sulfite is also harmful, and its toxicity is mainly manifested in the fo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D209/60C07D405/06C07D401/06G01N21/64
CPCC09K11/06C07D209/60C07D401/06C07D405/06C09K2211/1029C09K2211/1088G01N21/6428
Inventor 曾林涛徐俊超潘健吴风
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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