Tetraphenylethylene-based polypyrazole nitrogen-containing heterocyclic compound as well as preparation method and application thereof

Abstract

The invention provides a tetraphenylethylene-based polypyrazole nitrogen-containing heterocyclic compound as well as a preparation method and application thereof. The tetraphenylethylene-based polypyrazole nitrogen-containing heterocyclic compound is 1,1,2,2-tetra(4-(pyrazol-4-yl)phenyl)ethylene has a chemical formula of C38H28N8 and has a structure as shown in a formula (I) which is described in the specification. According to the invention, 1,1,2,2-tetra(4-(pyrazol-4-yl)phenyl)ethylene is an important hydrogen bond acceptor and can be used for constructing an hydrogen bond organic grid structure by using the weak hydrogen bond interaction of 1,1,2,2-tetra(4-(pyrazol-4-yl)phenyl)ethylene; and meanwhile, a pyrazole group has abundant coordination active action points, so metal ions are bonded or recognized through a metal-organic coordination effect. The tetraphenylethylene tetrapyrazole nitrogen-containing heterocyclic compound provided by the invention, as a metal ion identifier, shows high sensitivity to metal mercury ions in a water system and an organic solvent system, and is not interfered by other anions.

Description

technical field

[0001] The invention relates to the field of supramolecular chemistry, in particular to a tetrastyrylpolypyrazole nitrogen-containing heterocyclic compound, 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] Metal ions play an important role in life systems and environments. The identification of metal ions has always been a field that supramolecular chemists attach great importance to. The characteristics of position configuration and sensitivity to environmental pH make the identification of...

Examples

Embodiment 1 4

[0032] Synthesis of embodiment 1 tetrastyryl polypyrazole nitrogen-containing heterocyclic compound

[0033] Weigh 1,1,2,2-tetrakis(4-bromophenyl)ethylene (1.23g, 1.91mmol) and tetrakis(triphenylphosphine)palladium (330mg, 0.14mmol) in a 100mL three-necked flask, add 20mL n-Butanol 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 under the protection of gas (nitrogen) The nicohol ester (4.00 g, 14.38 mmol) was stirred at 120° C. for 72 hours.

[0034] 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 1,1,2,2-tetrakis(4-(1-(tetrahydro pyran-4-yl)-1H-pyrazol-4-yl)phenyl)ethylene. The product 1,1,2,2-tetrakis(4-(1-(tetrahydropyran-4-yl)-1H-pyrazol-4-yl)phenyl)ethene was dissolved in methanol 20ml, and dilute Hydroc...

Embodiment 2

[0040] Embodiment 2 The selectivity of the ion recognition body of the present invention to metal mercury ions

[0041] Take 4.8 mg of the compound of formula (I) prepared by the present invention as an ion recognizer, add the ion recognizer into a sample bottle, and prepare a 0.01 mM clear solution with DMA. Prepare Hg(NO 3 ) 2 An aqueous solution of mercury ions, with a concentration of 0.01M, and a mixed aqueous solution of other transition metal ions, respectively Zn(NO 3 ) 2 , Cu(NO 3 ) 2 , Cd(NO 3 ) 2 , Co(NO 3 ) 2 , Ni(NO 3 ) 2 , Al(NO 3 ) 3 , Fe(NO 3 ) 3 , Ag(NO 3 ), Al(NO 3 ) 3 , K 2 CO 3 , the concentration is 0.01M.

[0042]Add this series of metal ion aqueous solutions to the system, only the addition of mercury ions causes the obvious solution color to turn green, and with 378nm as the fluorescence excitation wavelength, the fluorescence intensity at around 520nm is enhanced by about 15 times, see the attached figure 1 . This result shows tha...

technical field

[0001] The invention relates to the field of supramolecular chemistry, in particular to a tetrastyrylpolypyrazole nitrogen-containing heterocyclic compound, 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] Metal ions play an important role in life systems and environments. The identification of metal ions has always been a field that supramolecular chemists attach great importance to. The characteristics of position configuration and sensitivity to environmental pH make the identification of...

Examples

Embodiment 1 4

[0032] Synthesis of embodiment 1 tetrastyryl polypyrazole nitrogen-containing heterocyclic compound

[0033] Weigh 1,1,2,2-tetrakis(4-bromophenyl)ethylene (1.23g, 1.91mmol) and tetrakis(triphenylphosphine)palladium (330mg, 0.14mmol) in a 100mL three-necked flask, add 20mL n-Butanol 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 under the protection of gas (nitrogen) The nicohol ester (4.00 g, 14.38 mmol) was stirred at 120° C. for 72 hours.

[0034] 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 1,1,2,2-tetrakis(4-(1-(tetrahydro pyran-4-yl)-1H-pyrazol-4-yl)phenyl)ethylene. The product 1,1,2,2-tetrakis(4-(1-(tetrahydropyran-4-yl)-1H-pyrazol-4-yl)phenyl)ethene was dissolved in methanol 20ml, and dilute Hydroc...

Embodiment 2

[0040] Embodiment 2 The selectivity of the ion recognition body of the present invention to metal mercury ions

[0041] Take 4.8 mg of the compound of formula (I) prepared by the present invention as an ion recognizer, add the ion recognizer into a sample bottle, and prepare a 0.01 mM clear solution with DMA. Prepare Hg(NO 3 ) 2 An aqueous solution of mercury ions, with a concentration of 0.01M, and a mixed aqueous solution of other transition metal ions, respectively Zn(NO 3 ) 2 , Cu(NO 3 ) 2 , Cd(NO 3 ) 2 , Co(NO 3 ) 2 , Ni(NO 3 ) 2 , Al(NO 3 ) 3 , Fe(NO 3 ) 3 , Ag(NO 3 ), Al(NO 3 ) 3 , K 2 CO 3 , the concentration is 0.01M.

[0042]Add this series of metal ion aqueous solutions to the system, only the addition of mercury ions causes the obvious solution color to turn green, and with 378nm as the fluorescence excitation wavelength, the fluorescence intensity at around 520nm is enhanced by about 15 times, see the attached figure 1 . This result shows tha...

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