Synthetic method and application of porphyrin type near-infrared sulfur ion fluorescence probe

A technique for fluorescent probes and synthesis methods, applied in the field of synthesis of porphyrin-type near-infrared fluorescent probes, to achieve the effects of reducing background fluorescence interference, simple synthesis routes, and high selectivity

Active Publication Date: 2015-09-30
HUNAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, most organic small molecule fluorescent probes designed and synthesized by the PET mechanism can detect sulfur ions in the ultraviolet and visible light regions, but few in the near-infrared region.

Method used

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  • Synthetic method and application of porphyrin type near-infrared sulfur ion fluorescence probe
  • Synthetic method and application of porphyrin type near-infrared sulfur ion fluorescence probe
  • Synthetic method and application of porphyrin type near-infrared sulfur ion fluorescence probe

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Effect test

Embodiment 1

[0030] A kind of synthetic method of porphyrin type near-infrared sulfur ion fluorescent probe (monohydroxyphenylporphyrin-2,4-dinitrobenzenesulfonate), specifically comprises the following steps:

[0031] (1) Weigh A (monohydroxyphenylporphyrin (30mg, 0.048mmol) and dissolve it in 10ml of refined dichloromethane, then add DIEA (0.019ml, 0.116mmol), then weigh B (2,4-dinitro Benzenesulfonyl chloride (17.7mg, 0.066mmol) was dissolved in 10ml of refined dichloromethane, filled with N 2 After protecting for 20 to 30 minutes, use a constant pressure dropping funnel to drop the solution of B into A, and stir at room temperature for 24 to 36 hours to obtain dichloromethane of monohydroxyphenylporphyrin-2,4-dinitrobenzenesulfonate solution;

[0032] (2) the dichloromethane solution of monohydroxyphenylporphyrin-2,4-dinitrobenzenesulfonyl ester is washed 3 to 4 times with 20ml saturated sodium chloride solution, and the organic layer is dried with anhydrous sodium sulfate ( Stir for...

Embodiment 2

[0034] Sulfur ion detection experiment.

[0035] (1) Add 5.0ml of THF, 1.16mmol L to a 10ml volumetric flask -1 Probe solution 86 μl, pH 7.4 0.2mol.L -1 0.5ml of phosphate buffer solution, 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, 0.5, 1.0, 2.0, 3.0, 4.0, 5.0, 6.0, 7.0, 8.0, 9.0, 10 μmol L -1 . Stir the reaction at room temperature for 8 minutes to measure its fluorescence emission spectrum (λ ex =550nm,λ em = 570nm). 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 8 minutes of reaction, the fluorescence intensity of the reaction system was significantly enhanced, and with the S 2- As the concentration inc...

Embodiment 3

[0038] Sulfide ion selectivity experiment.

[0039] (1) Add 5.0ml THF, 1.16mmol.L, to a 10ml volumetric flask -1 Probe solution 86 μl, pH 7.4 0.2mol.L -1 0.5ml of phosphate buffer solution, 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 anion: S 2- , I - , Cl - , Br - ,C 2 o 4 2- , SO 3 2- , HSO 3 - , F - ,NO 2 - , Ac - , SO4 2- ,NO 3 - , S 2 o 3 2- , CO 3 - , SCN - , HCO 3 - , so that the concentration is 5μmol.L -1 , measured its fluorescence intensity (λ ex =550nm;λ em =570nm), obtain the fluorescence emission spectrum figure after probe reacts with different anions (see Figure 5 ). Depend on Figure 5 It can be seen that adding S 2- After adding the same concentration of other anions, the fluorescence intensity was significantly enhanced, but the fluorescence intensity was almost unchanged after adding the same concentration of...

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Abstract

The invention discloses a synthetic method and application of a porphyrin type near-infrared sulfur ion fluorescence probe. The fluorescence probe is prepared by reaction of TPP-OH and 2,4-dinitrobenzene sulfonyl chloride as raw materials, N,N-DIEA as a catalyst and dichloromethane as a solvent at room temperature. The probe can carry out fluorescence detection of high sensitivity and selectivity on sulfur ions. Compared with an existing small organic molecule fluorescence probe, the obtained fluorescence probe has longer fluorescence emission wavelength (lambda em > 650 nm), can carry out detection of high sensitivity, selectivity and timeliness on the micro sulfur ions on a near infrared region, and has huge application prospects in the biological and environment detection field.

Description

technical field [0001] The invention relates to the technical field of preparation of fluorescent sensing materials and detection of biological and environmental ions, in particular, relates to 2- ) function of the porphyrin-type near-infrared fluorescent probe synthesis method and its application in the detection of sulfide ions. Background technique [0002] Sulfide ions exist in some industrial wastewater and domestic sewage, and protonation will produce highly toxic hydrogen sulfide, which is a recognized environmental pollutant; sulfur ions in organisms are protonated to form hydrogen sulfide gas, and protonated sulfide ions participate in Respiratory system, gastrointestinal system and endocrine system and other physiological and pathological regulation processes, once the sulfur ion concentration cannot maintain the normal physiological concentration level, it will cause various diseases such as pulmonary hypertension, gastric mucosal injury, liver cirrhosis, etc.; th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22C09K11/06G01N21/64
CPCC07D487/22C09K11/06C09K2211/1007C09K2211/1029C09K2211/1074G01N21/64
Inventor 曾荣今成奋民吴湘思刘玛丽陈国良陈述龙云飞陈冠凡
Owner HUNAN UNIV OF SCI & TECH
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