Near-infrared fluorescent probe for detecting thiophenol and synthesis method and application thereof

A synthesis method and technology of fluorescent molecular probes, applied in the field of detection of thiophenol, can solve the problems of unfavorable complex environmental samples and biological sample detection, weak biological penetration ability, biological damage, etc., and achieve high sensitivity and high Selective, responsive effects

Inactive Publication Date: 2019-05-17
SHANGQIU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the fluorescent probe molecules currently used to detect thiophenols do not have emission wavelengths in the near-infrared region or the Stokes shift value of the probe is small (Zhang W.J. Dyes and Pigments 2016, 133, 248; Pagidi S. Langmuir 2018, 34,8170; Genga Y.Sensors&Actuators:B.Chemical2018,273,1670.), due to the weak penetrating ability of light in the shorter wavelength band and the existence of biological damage, and the small Stokes shift value will bring excitation Therefore, this kind of probe molecule is not conducive to the elimination of complex sample background interference, which is not conducive to the detection of complex environmental samples and biological samples

Method used

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  • Near-infrared fluorescent probe for detecting thiophenol and synthesis method and application thereof
  • Near-infrared fluorescent probe for detecting thiophenol and synthesis method and application thereof
  • Near-infrared fluorescent probe for detecting thiophenol and synthesis method and application thereof

Examples

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Effect test

Embodiment 1

[0034] Example 1: Synthesis of Fluorescent Molecular Probes

[0035] Compound 2 (0.361g, 1mmol), 2,4-dinitrofluorobenzene (0.186g, 1mmol) was added to K 2 CO 3 (0.685g, 5mmol), the solvent acetonitrile (20mL) was reacted at 80°C for 8h. After the reaction was completed, the solvent was distilled off under reduced pressure, and the product was separated by column chromatography (dichloromethane as the eluent) to obtain 0.422 g of the product as a red-black solid (yield: 80%). The product structural formula is as follows:

[0036]

[0037] 1 H NMR (400Hz, CDCl 3 ): δ8.44(d, J=8.3Hz, 1H), 7.68(d, J=9.1Hz, 1H), 7.00(d, J=16.0Hz, 1H), 6.85(d, J=16.0Hz, 1H ),6.79–6.69(m,2H),6.56(d,J=8.3Hz,1H),6.43(s,1H),3.41(q,J=7.0Hz,4H),2.50(s,2H),2.20 (s,2H),1.22(t,J=7.1Hz,6H),0.96(s,6H)MS[ESI]:m / z,calcd for[M+H] + 528.082; found 528.22.

Embodiment 2

[0038] Example 2: Fluorescent detection of probes to thiophenol

[0039] The molecular probe prepared above was dissolved in a mixed buffer solution of water and dimethyl sulfoxide (H 2 O / DMSO=1 / 1, v / v, 10mM HEPES, pH 7.4)), prepared to 10μmol L -1 probe solution. Add 2 mL of prepared 10 μmol L to a 3 mL cuvette-1 Probe solution of the present invention, then add different concentrations of thiophenol and mix evenly, test its fluorescence spectrum, the results are as follows image 3 shown. The fluorescence emission intensity of the solution at 693nm is plotted against the concentration of thiophenol, and the concentration of thiophenol is 0.5–10 μmol L -1 In the range, there is a good linear relationship between the two ( Figure 4 ), the quantitative detection of thiophenol in this concentration range can be realized, and the solution changes from red to blue, which is also suitable for naked eye detection. And this probe is not affected by some other common substances,...

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Abstract

The invention discloses a near-infrared fluorescent probe for detecting thiophenol and a synthesis method and application thereof, and belongs to the technical field of chemical analysis and detection. The near-infrared fluorescent probe is obtained by reaction between a dicyano-substituted isophorone large pi system and 2,4-dinitrofluorobenzene, and has the following structure (being defined as in the specification). Fluorophore of the probe is the dicyano-substituted isophorone large pi system, and a response group to thiophenol is 2,4-dinitrophenoxy. Molecules of the probe have high selectivity and sensitivity to thiophenol, the detection range is 0.5-10 [mu]mol.L<-1>, and the limit of detection is 23 nmol.L<-1>. The probe can be used for detecting thiophenol in water bodies, soil and cells.

Description

technical field [0001] The invention belongs to the technical field of chemical analysis and detection, and in particular relates to a near-infrared trun-on fluorescent probe for detecting thiophenol, a synthesis method thereof and an application in detecting thiophenol. Background technique [0002] Thiophenol (C 6 h 5 SH, PhSH) is a highly reactive aryl sulfide, which is widely used in the synthesis industry, such as the synthesis of sulfa drugs, pesticides and polymers. But on the other hand, thiophenol is highly toxic, and inhalation and skin intake can lead to various diseases, such as dyspnea, muscle weakness, central nervous system damage and even death. The U.S. Occupational Safety and Health Administration limits the maximum concentration of thiophenol in the working environment to 0.1ppm. With the large amount of industrial use of thiophenols, emissions and toxic effects, it is very necessary to develop a method for the detection and protection of thiophenols wi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/43C07C253/30C09K11/06G01N21/359G01N21/78G01N21/64
Inventor 吴萍郝远强马啸华
Owner SHANGQIU NORMAL UNIVERSITY
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