Polypyrazole nitrogen heterocyclic compound as well as preparation and application thereof

A nitrogen-heterocyclic compound and polypyrazole technology, which is applied in the direction of analyzing materials through chemical reactions, organic chemistry, and material analysis through observation of the impact on chemical indicators, can solve environmental pH sensitivity and other problems

Active Publication Date: 2019-03-12
BEIJING UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Anions play an important role in life systems and environments. The identification of anions has always been a field that supramolecul

Method used

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  • Polypyrazole nitrogen heterocyclic compound as well as preparation and application thereof
  • Polypyrazole nitrogen heterocyclic compound as well as preparation and application thereof
  • Polypyrazole nitrogen heterocyclic compound as well as preparation and application thereof

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Embodiment 1

[0033] Embodiment 1: the synthesis of polypyrazole nitrogen-containing heterocyclic compound

[0034] Weigh tris[(5-bromopyridine)-2-methyl)]amine (552mg, 1.05mmol) and tetrakis(triphenylphosphine)palladium (244mg, 0.22mmol) in a 100mL three-necked flask, add 20mL n-butyl Alcohol and 10ml of water, install a reflux device, add 4mL of 2M potassium carbonate aqueous solution, add 1-(tetrahydropyran-4-yl)-1H-pyrazole-4-boronic acid pinacol under the protection of gas (nitrogen) The ester (1.18g, 4.19mmol) was stirred at 120°C for 72 hours.

[0035] The solvent was distilled off under reduced pressure, the resulting product was dissolved in dichloromethane, extracted three times with water, the organic layer was taken, and the solvent was removed; the product tri((5-(1-(tetrahydropyran-4-yl) -1H-pyrazol-4-yl)pyridin-2-yl)methyl)amine. The product tris((5-(1-(tetrahydropyran-4-yl)-1H-pyrazol-4-yl)pyridin-2-yl)methyl)amine was dissolved in methanol 20ml, and dilute hydrochloric ac...

Embodiment 2

[0040] Embodiment 2: the selectivity of the ion recognition body of the present invention to halide ions:

[0041] Take 4.8 mg of the compound of formula (I) prepared by the present invention as an ion recognition body, add the ion recognition body into a sample bottle, and prepare a 5 mM turbid aqueous solution. Prepare various halogen ion sodium salt solutions with deionized water, the concentration is 5mM, respectively NaCl, NaBr, NaI, NaF aqueous solution, and other non-halogen ion aqueous solutions, respectively Na 2 SO 4 , NaNO 3 , Na 2 CO 3 , Na 3 PO 4 , NaC 2 o 4 , the concentration is 5mM.

[0042] Add this series of ionic aqueous solutions to the system, only the addition of halide ions causes the obvious solution to turn yellow and clear. This result shows that the ion recognizer of the present invention has a high degree of recognition for halogen ions.

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Abstract

The invention provides a polypyrazole nitrogen heterocyclic compound as well as preparation and application thereof. The polypyrazole nitrogen heterocyclic compound is tris((5-(pyrazol-4-yl)pyridin-2-yl)methyl)amine, the chemical formula thereof is C27H24N10, the structural formula is shown in the description, the tris((5-(pyrazol-4-yl)pyridin-2-yl)methyl)amine is an important hydrogen bond acceptor and can be used for constructing an identifier of anions by utilizing the weak interaction of hydrogen bonds of the tris((5-(pyrazol-4-yl)pyridin-2-yl)methyl)amine. The polypyrazole nitrogen heterocyclic compound provided by the invention, which serves as a halide ion identifier, has high sensitivity to fluorine, chlorine, and bromide ions in an aqueous system, and is not interfered by other anions.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and specifically relates to a polypyrazole nitrogen-containing heterocyclic compound and a preparation method and application thereof. Background technique [0002] Pyrazole compounds are compounds with nitrogen heterocyclic structure, which have excellent biological and physiological activities. In recent years, many pyrazole compound pesticides have been commercialized one after another. The bactericidal performance of pyrazole compounds has also become a research hotspot. In terms of health care and plant protection, many pyrazole compounds have shown wide application and development prospects. [0003] Anions play an important role in life systems and environments. The identification of anions has always been a field that supramolecular chemists have attached great importance to. The characteristics such as pH sensitivity make the identification of anions a challenging problem. So far, the ...

Claims

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Application Information

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IPC IPC(8): C07D401/14G01N21/77G01N21/75
CPCC07D401/14G01N21/75G01N21/77G01N2021/755
Inventor 童金于澍燕
Owner BEIJING UNIV OF TECH
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