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Pyrazolopyridine aldehyde sulfite ion fluorescent probe

A technology of pyrazolopyridine aldehyde sulfites and fluorescent probes, which can be used in fluorescence/phosphorescence, luminescent materials, organic chemistry, etc., and can solve problems such as low application reporting.

Active Publication Date: 2019-05-21
张智涵
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Pyrazolo[1,5-a]pyridine compounds are limited by limited synthesis methods, and their applications in the optical field are rarely reported, and their applications as fluorescent probes for sulfite ions have not been reported in the literature.

Method used

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  • Pyrazolopyridine aldehyde sulfite ion fluorescent probe
  • Pyrazolopyridine aldehyde sulfite ion fluorescent probe
  • Pyrazolopyridine aldehyde sulfite ion fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Embodiment 1: the synthetic scheme of formula (1) compound is shown in the following formula:

[0015]

[0016] Concrete synthetic steps are as follows:

[0017] Add 0.27g (1.00mmol) ethyl 2-phenylpyrazolo[1,5-a]pyridine-5-carboxylate, 0.38g (10.00mmol) sodium borohydride, 15mL ethanol successively in a 25mL round bottom flask, Reflux reaction at 80°C for 10 hours, pour into 100mL water, precipitate solid, filter with suction, and dry to obtain 0.20g colorless solid product 2-phenyl-5-hydroxymethylpyrazolo[1,5-a]pyridine, producing The rate is 89.3%.

[0018] H NMR spectrum, carbon spectrum determination: 1 H NMR (DMSO-d 6 ,400MHz),δ8.63(d,J=8.0Hz,1H),7.98(d,J=8.0Hz,2H),7.55(s,1H),7.47(m,2H),7.38(m 1H), 7.00(s,1H),6.81(dd,J=8.0Hz,4.0Hz,1H),5.42(t,J=8.0Hz,1H),4.54(d,J=8.0Hz,2H). 13 C NMR (DMSO-d 6 ,100MHz), δ157.74, 146.32, 144.23, 138.17, 133.96, 133.53, 131.15, 118.62, 116.70, 98.46, 67.12.

Embodiment 2

[0020]

[0021] Concrete synthetic steps are as follows:

[0022] 0.23g (1.00mmol) 2-phenyl-5-hydroxymethylpyrazolo[1,5-a]pyridine, 0.87g (10.00mmol) manganese dioxide, 15mL tetrahydrofuran, 70 The reaction was refluxed for 10 hours at high temperature, concentrated, and 0.13 g of colorless solid product 2-phenyl-5-formylpyrazolo[1,5-a]pyridine was obtained by column chromatography, with a yield of 58.6%.

[0023] H NMR spectrum, carbon spectrum determination: 1 H NMR (DMSO-d 6 ,400MHz),δ9.97(s,1H),8.52(d,J=8.0Hz,1H),8.03(s,1H),7.98(d,J=8.0Hz,2H),7.48(t,J= 8.0Hz, 2H), 7.41(m, 1H), 7.24(m, 1H), 7.10(s, 1H). 13 C NMR (DMSO-d 6 ,100MHz), δ189.66, 154.98, 140.36, 132.36, 131.76, 129.21, 128.94, 128.86, 126.51, 124.53, 109.99, 107.70, 98.03.

Embodiment 3

[0025] To formula (1) compound (10 -6 M) in the ethanol aqueous solution (ethanol: water=3:7) add the Na of 100 equivalents + ,Mg 2+ ,Zn 2+ ,Fe 3+ ,Cu 2+ ,F - ,Br - , I - , HCO 3 - , NO 3 - , ClO - , SO 4 2- , SCN - , S 2 o 3 2- , S 2- and SO 3 2- Afterwards, measuring its fluorescence emission intensity change at 500nm place finds: formula (1) compound is to SO 3 2- It has good fluorescence selectivity, and its fluorescence intensity is obviously weakened at 500nm, such as figure 1 shown.

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Abstract

The invention discloses a pyrazolopyridine aldehyde sulfite ion fluorescent probe. The fluorescent probe is a 2-phenyl-5-formylpyrazolo[1,5-a] pyridine sulfite ion fluorescent probe. The fluorescent probe has the advantages that the fluorescent probe has better selectivity and higher sensitivity to sulfite ions in an ethanol water solution. Compared with an existing probe, the probe has the obvious advantages that the probe is not interfered by other ions and the like, and has a great application prospect.

Description

technical field [0001] The invention belongs to the technical field of organic small molecule fluorescent probes, and relates to a novel sulfite ion fluorescent probe 2-phenyl-5-formylpyrazolo[1,5-a]pyridine and an application thereof. Background technique [0002] Sulfite has the functions of inhibiting bacterial growth and anti-oxidation, so it is used as an antioxidant and preservative in the food and wine industry. However, high doses of sulfites can cause diarrhea, low blood pressure, and allergic and asthmatic reactions in susceptible individuals. Countries around the world also have strict regulations on the amount of sulfites added to food. Therefore, it is particularly important to detect the sulfite content in food and beverages. [0003] Due to the advantages of good selectivity, high sensitivity, simple operation, low cost and real-time monitoring, fluorescent probes are widely used in the determination of sulfite ion content. Although a variety of fluorescent...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C09K11/06G01N21/64
Inventor 张智涵葛燕青
Owner 张智涵
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