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Compounding method and application of fluorescent probe for double-channel detection of hydrogen sulfide

A fluorescent probe, hydrogen sulfide technology, applied in the field of synthesis of long-wavelength fluorescent probes, can solve the problems of poor selectivity, complicated measurement operation, high cost, etc., and achieve the effect of good stability and simple preparation method

Active Publication Date: 2017-07-21
TAIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Traditional hydrogen sulfide determination methods mainly rely on colorimetric methods, electrochemical analysis methods, metal sulfide precipitation methods, etc., but these methods have poor selectivity, complex measurement operations, high cost, and are not easy to popularize and apply.

Method used

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  • Compounding method and application of fluorescent probe for double-channel detection of hydrogen sulfide
  • Compounding method and application of fluorescent probe for double-channel detection of hydrogen sulfide
  • Compounding method and application of fluorescent probe for double-channel detection of hydrogen sulfide

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Experimental program
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Effect test

Embodiment 1

[0018] Under nitrogen protection, accurately weigh rhodamine compound II (780mg, 1.64mmol), p-hydroxybenzaldehyde (500mg, 1.64mmol), dissolve in 20mL of ethanol, and then add 1 drop of piperidine to the mixture, at 80°C The reaction was stirred at reflux for 10 hours. TLC detected that the reaction was complete, and the reaction was stopped. The solvent was distilled off under reduced pressure, and separated and purified by column chromatography to obtain 1.03 g of a dark green product (Compound I), with a yield of 82.5%. 1 H NMR (400MHz, DMSO-d 6 )δ8.34(s,1H),8.10(d,J=4.0Hz,2H),7.94(d,J=8.0Hz,1H),7.79(t,J=8.0Hz,1H),7.68(t, J=8.0Hz, 2H), 7.34(t, J=12.0Hz, 2H), 6.76(d, J=8.0Hz, 1H), 6.47-6.38(m, 3H), 3.60(q, 4H), 3.37( q,4H),1.78-1.54(m,6H),1.21(t,J=8.0Hz,6H),1.10(t,J=6.0Hz,6H); HR-ESI-MS m / z:[M] +calcd.for663.2620 found 663.2618.

Embodiment 2

[0020] Under nitrogen protection, accurately weigh rhodamine compound II (780mg, 1.64mmol) and p-hydroxybenzaldehyde (500mg, 1.64mmol), dissolve them in 20mL of ethanol, then add 3 drops of piperidine dropwise to the mixture, at 80°C The reaction was stirred at reflux for 6 hours. TLC detected that the reaction was complete, and the reaction was stopped. The solvent was distilled off under reduced pressure, and separated and purified by column chromatography to obtain 1.18 g of a dark green product (Compound I), with a yield of 94.5%.

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Abstract

The invention belongs to the field of fluorescent probes for chemical analysis, and relates to a compounding method and application of a novel long-wavelength fluorescent probe for double-channel detection of hydrogen sulfide. The compounding method includes that a target probe compound is obtained from aldol reaction between a rhodamine-like derivative and aldehyde coumarin with the presence of a basic catalyst. The preparation method of the probe is simple, stability is high, the background fluorescence is weak, the probe can response to the hydrogen sulfide selectively and sensitively, the ultraviolet spectrum has a ratio-type change and is accompanied by about 130 nanometers of red shift, double-channel reinforcement of the fluorescence spectrum occurs in 662nm and 818nm, injuries to living organisms are small, and accordingly, the probe has a good application prospect in the fields such as biological imaging.

Description

technical field [0001] The invention relates to a synthesis method and application of a novel double-channel long-wavelength fluorescent probe for detecting hydrogen sulfide. Background technique [0002] For many years, hydrogen sulfide (H 2 S) This gas with a special smell has been deeply researched as a kind of environmental pollution gas. However, recent studies have found that hydrogen sulfide (H 2 S) is also the third endogenous gas signaling molecule after nitric oxide (NO) and carbon monoxide (CO). Endogenous H 2 S mainly comes from the enzymatic hydrolysis of L-cysteine. At normal physiological concentrations, H 2 S is involved in regulating a series of physiological processes such as myocardial contraction, vascular tension, nerve conduction and insulin secretion. However, once the normal H in the cell cannot be maintained 2 S concentration, it will cause diseases such as arterial and pulmonary hypertension, Alzheimer's disease, gastric mucosal injury and li...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/82C09K11/06G01N21/64
CPCC07D311/82C09K11/06C09K2211/1088G01N21/643
Inventor 厉凯彬韩得满陈逢灶
Owner TAIZHOU UNIV
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