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Preparation method and application of hydroxyl porphyrin-based high-selectivity near-infrared fluorescence sulfur ion probe

A high-selectivity, hydroxyporphyrin technology, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., to achieve the effect of simple synthesis route, easy purification, improved resolution and accuracy

Active Publication Date: 2016-02-03
HUNAN UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, most organic small molecule fluorescent probes designed and synthesized according to the PET mechanism can detect sulfur ions in the ultraviolet and visible light region, while the detection in the near-infrared light region is relatively small, so the development of porphyrin-based fluorescent probes has important application value

Method used

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  • Preparation method and application of hydroxyl porphyrin-based high-selectivity near-infrared fluorescence sulfur ion probe
  • Preparation method and application of hydroxyl porphyrin-based high-selectivity near-infrared fluorescence sulfur ion probe
  • Preparation method and application of hydroxyl porphyrin-based high-selectivity near-infrared fluorescence sulfur ion probe

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Embodiment 1

[0032] A preparation method based on porphyrin-based highly selective near-infrared sulfur ion fluorescent probe (monohydroxyphenylporphyrin-7-nitrobenzofurazan), specifically comprising the following steps:

[0033] (1) Weigh monohydroxyphenylporphyrin (30mg, 0.048mmol) and DMAP (0.014ml, 0.116mmol) and dissolve them in 10ml refined dichloromethane to obtain solution A; then weigh 4-chloro-7-nitrobenzene Furazan (13.2 mg, 0.066 mmol) was dissolved in 10 ml of refined dichloromethane to obtain solution B. Fill solution A with N 2 After protecting for 20 to 30 minutes, slowly drop the solution of B into A with a constant pressure dropping funnel, and stir at room temperature for 24 to 36 hours to obtain monohydroxyphenylporphyrin-7-nitrobenzofurazan (TPP-O- NBD) in dichloromethane;

[0034](2) Wash the dichloromethane solution of TPP-O-NBD with saturated sodium chloride solution 3 to 4 times, each time with 15-20mL saturated sodium chloride solution, and then dry the organic ...

Embodiment 2

[0037] Sulfur ion detection experiment.

[0038] (1) Add 5.0ml of THF, 1.50mmol L to a 10ml volumetric flask -1 Probe solution 66.5 μl, pH 7.4 1.0mol.L -1 0.5ml of 4-hydroxyethylpiperazineethanesulfonic acid (HEPES) buffer solution was diluted to 10ml with twice distilled water to obtain a concentration of 10μmol L -1 probe solution. Take 3.0ml probe solution and add it into 4ml cuvette, add S 2- , so that the concentrations are 0, 1.0, 3.0, 5.0, 7.0, 9.0, 15.0, 20.0, 25.0, 30.0 μmol L -1 . Stir the reaction at room temperature for 5 minutes to measure its fluorescence emission spectrum (λ ex =428nm,λ em = 652nm). to obtain probes with different concentrations of S 2- The fluorescence emission spectrum of the reaction (see image 3 ). Depend on image 3 It can be seen that the fluorescence intensity of the probe solution itself is very small, when adding S 2- After 5 minutes of reaction, the fluorescence intensity of the reaction system was significantly enhanced, ...

Embodiment 3

[0041] Sulfide ion selectivity experiment.

[0042] (1) Add 5.0mlTHF, 1.50mmol.L, to a 10ml volumetric flask -1 Probe solution 66.5 μl, pH 7.4 1.0mol.L -1 0.5ml of HEPES buffer solution, dilute to 10ml with twice distilled water, and obtain a concentration of 10μmol L -1 Probe solution. Take 3.0ml probe solution and add it to 4ml cuvette, add anion or related species respectively: S 2- , I - , Cl - , Br - ,C 2 o 4 2- , SO 3 2- , HSO 3 - , F - ,NO 2 - , SO4 2- ,NO 3 - , S 2 o 3 2- , CO 3 - , SCN - , HCO 3 - , Cys, Asp, H 2 o 2 , ClO - , GSH. Make S 2- The concentration is 30μmol.L -1 , the concentration of other ions and related species is 300 μmol.L -1 , after stirring at room temperature for 5 minutes, measure its fluorescence intensity (λ ex =428nm), get the fluorescence emission spectrum after the probe reacts with different anions or related species (see Figure 5 ). Depend on Figure 5 It can be seen that adding S 2- After adding othe...

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Abstract

The invention discloses a preparation method and application of a hydroxyl porphyrin-based high-selectivity near-infrared fluorescence sulfur ion probe. The fluorescence probe is prepared by taking 5-hydroxyphenyl-11,15,20-triphenylporphyrin (TPP-OH) and 4-chlorine-7-nitro-1,2,3-benzoxadiazole (NBD-Cl) as materials, taking 4-dimethylamino pyridine (DMAP) as a catalyst, taking dichloromethane as a solvent and performing one step reaction under room temperature. The preparation method of the probe is simple, and a product is easy to separate and purify. Compared with an existing small organic molecule fluorescence probe, the fluorescence probe obtained by the preparation method has higher fluorescence emission wavelength (lumbda em is greater than 650nm), high-sensitivity and high-selectivity quick recognition and detection on a trace of hydrogen sulphide can be realized in a near-infrared region, and the application prospect is great in the field of environmental and biological detection.

Description

technical field [0001] The invention relates to the technical field of fluorescent sensing material preparation and biological and environmental detection, in particular, relates to a 2- ) function-based preparation method of highly selective near-infrared fluorescent probes based on hydroxyporphyrin and in S 2- application in detection. Background technique [0002] Sulfide ions exist in some industrial wastewater and domestic sewage, and are a highly toxic environmental pollutant; sulfur ions in organisms undergo protonation to form endogenous hydrogen sulfide (H 2 S), many studies in recent years have shown that endogenous H 2 S is the third endogenous gas signal molecule discovered after nitric oxide (NO) and carbon monoxide (CO). Endogenous hydrogen sulfide participates in many physiological and pathological regulation processes such as cardiovascular system, digestive system and nervous system. Once the sulfide ion concentration in the organism cannot maintain the ...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D487/22G01N21/64
Inventor 曾荣今成奋民刘玛丽吴湘思陈国良陈述陈冠凡龙云飞
Owner HUNAN UNIV OF SCI & TECH
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