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Carbazole fluorescent probe and preparation method and application thereof

A fluorescent probe and carbazole technology, applied in the field of fluorescent probes, can solve problems such as environmental pollution and toxicity, and achieve the effects of high sensitivity, good cell membrane penetration, and simple detection means.

Inactive Publication Date: 2015-12-30
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

CN - Can be used in the production of artificial fibers, resins and herbicides, HSO 3 - As an antibacterial agent, enzyme inhibitor, antioxidant in food and pharmaceutical products are widely used, but they also cause environmental pollution while benefiting human beings, especially CN - , which has great toxicity, it can be absorbed by the human body through the lungs, intestinal tract and skin, etc., resulting in headache, vomiting, neurasthenia syndrome, kidney and heart damage, hypogonadism and thyroid function , auditory and visual and nervous system disorders, etc., eventually leading to death

Method used

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  • Carbazole fluorescent probe and preparation method and application thereof
  • Carbazole fluorescent probe and preparation method and application thereof
  • Carbazole fluorescent probe and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] The preparation of embodiment 1 carbazole fluorescent probe IECBT:

[0049] (1) In a container, mix N-ethylcarbazole-3-carbaldehyde and 2,3-dimethylbenzothiazole iodide at a molar ratio of 1:1 and dissolve in absolute ethanol, and heat to 150 in an oil bath ℃, reflux reaction for 6 hours, take out after cooling;

[0050] (2) After spot plate observation confirmed that the reaction was complete, the mixture was filtered and washed with suction to obtain an orange-red solid product with a yield of 55%.

[0051] Probe for IECBT 1 HNMR, 13 CNMR characterization, the results are as follows:

[0052] 1 HNMR (300MHz, DMSO): δ8.42(d, J=9.0Hz, 3H), 8.22(s, 3H), 8.07(d, J=15.6Hz, 1H), 7.84(m, J=38.4Hz, 4H ),7.56(t,J=15.3Hz,1H),7.37(t,J=14.4Hz,1H),4.55(d,J=6.9Hz,2H),4.37(s,3H),1.39(t,J =13.8Hz,3H)

[0053] 13 CNMR(75MHz,DMSO):δ171.05,149.67,141.30,141.10,139.40,128.26,127.19,126.46,125.95,124.29,123.18,122.81,122.04,121.32,119.72,119.37,115.58,109.20,36.531,35.26,12.94

Embodiment 2

[0054] The CN of embodiment 2 fluorescent probe IECBT - Titration fluorescence plot

[0055] Add 20 μL fluorescent probe IECBT stock solution to 2 mL DMSO system for CN - Fluorescence titration experiment is detected on a fluorescence spectrophotometer. With the addition of the sample to be tested, the fluorescence intensity at 575nm is gradually weakened, and the emission peaks at 360nm and 376nm are enhanced. Instrument parameters: the slit widths of the excitation wavelength and emission wavelength are 10.0nm and 5.0nm respectively, and the maximum excitation wavelength of the fluorescent probe solution is: λ ex 340nm and the maximum fluorescence emission wavelength is: λ em 575nm.

Embodiment 3

[0056] CN of embodiment 3 fluorescent probe IECBT - Titration UV diagram

[0057] Add 30 μL fluorescent probe IECBT stock solution to 2 mL DMSO system for CN - The ultraviolet titration experiment is detected on the ultraviolet spectrophotometer. With the addition of the sample to be tested, the ultraviolet absorption intensity at 468nm gradually weakens, and the ultraviolet absorption intensity at 266nm and 295nm gradually increases.

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Abstract

The invention discloses a carbazole fluorescent probe and a preparation method and application thereof. The preparation method of the probe comprises the steps that N-ethyl carbazole-3-formaldehyde and 2,3-dimethyl benzothiazole iodide are mixed according to the molar ratio of one to one and dissolved in absolute ethyl alcohol, a mixture is heated to 150 DEG C in an oil bath, reflux reaction is conducted for 6 h, the reaction is observed to be completed by thin-layer chromatography after cooling, suction filtration and washing are conducted on the mixture, and then a red orange solid product is obtained. According to the probe, high sensitivity and selectivity are simultaneously displayed on CN-, HSO3- and pH in different systems, especially when the probe is used for detecting CN- ions, large Stocks displacement is displayed, the detection process is simple, convenient and rapid, and the detection result is accurate. Fluorescence imaging of the fluorescent probe in living cells can be obtained by combining with a laser confocal scanning microscopic technology.

Description

technical field [0001] The invention relates to a fluorescent probe, in particular to a carbazole-based fluorescent probe and a preparation method and application thereof. Background technique [0002] CN - 、HSO 3 - and pH are of great significance in modern industry and production life. CN - Can be used in the production of artificial fibers, resins and herbicides, HSO 3 - As an antibacterial agent, enzyme inhibitor, antioxidant in food and pharmaceutical products are widely used, but they also cause environmental pollution while benefiting human beings, especially CN - , which has great toxicity, it can be absorbed by the human body through the lungs, intestinal tract and skin, etc., resulting in headache, vomiting, neurasthenia syndrome, kidney and heart damage, hypogonadism and thyroid function , auditory and visual and nervous system disorders, etc., eventually leading to death. Excess intake of HSO 3 - There will be deleterious effects on tissues, cells, and ...

Claims

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Application Information

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IPC IPC(8): G01N21/64
Inventor 钞建宾李志清张永斌
Owner SHANXI UNIV
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