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Porphyrin cage compound, and preparation method and application thereof

A compound and porphyrin cage technology, which is applied to the application field of porphyrin cage compounds in the detection of polynitrogen anions, can solve the problems of low yield, single output signal, complex synthesis process and the like, and achieves simple process and detection sensitivity. High and broad application prospects

Inactive Publication Date: 2014-04-16
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These recognition systems usually have disadvantages such as complex synthesis process, low yield, single output signal, etc.

Method used

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  • Porphyrin cage compound, and preparation method and application thereof
  • Porphyrin cage compound, and preparation method and application thereof
  • Porphyrin cage compound, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] The preparation of porphyrin cage compound shown in embodiment 1, formula (I)

[0035] (1) Preparation of compound shown in formula (II)

[0036] In a two-necked flask with a capacity of 500 ml, 1.61 g (10 mmol) of 4-(azidomethyl) benzaldehyde and 0.67 g of pyrrole (10 mmol) were dissolved in 400 ml of chloroform, nitrogen gas was passed for 30 minutes, and then trifluorinated Boron ether solution 356 microliters (2.8mmol); After reacting at room temperature for 1 hour, add 1.96 grams of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) (8.6mmol), and then After reacting for half an hour, 389 microliters (2.8 mmol) of triethylamine were added, and after stirring for 5 minutes, a methanol solution (18 ml) of 4.53 grams (30 mmol) of zinc acetate was added; stirring was continued for 12 hours, the reaction was stopped, and the organic mixture was concentrated under vacuum. Phase, select sherwood oil: trichloromethane (volume ratio V / V=1: 1) mixed solvent to make eluting agent...

Embodiment 2

[0044] The preparation of porphyrin cage compound shown in embodiment 2, formula (I)

[0045] (1) Preparation of compound shown in formula (II)

[0046] The specific preparation steps are the same as step (1) in Example 1.

[0047] (2) Preparation of porphyrin cage compound shown in formula (I)

[0048] Add 350 milliliters of toluene and 4.93 milliliters (2.81mmol) of diisopropylethylamine (2.81mmol) and CuI 9.5 milligrams (0.05mmol) in the two-necked flask of 500 milliliters, logical argon 30 minutes, use constant pressure dropping funnel then to formula ( 100 ml of toluene solution of 89.4 mg (0.1 mmol) of the compound shown in III) and 89.6 mg (0.1 mmol) of the compound shown in formula (II) was dropped into the reaction system composed of toluene, diisopropylethylamine and CuI , the dripping speed is required to be slow, and the time is controlled within 12 hours. After the dripping, the reaction is continued at room temperature for 15 hours, and the reaction is stopped....

Embodiment 3

[0049] Embodiment 3, the porphyrin cage compound shown in formula (I) is used as detection reagent to carry out the detection of ultraviolet-visible absorption spectrum to azide anion

[0050] In a cuvette, dissolve the porphyrin cage compound shown in formula (I) in dichloromethane at a concentration of 5 μM, and add tetrabutylammonium azide (TBAN 3 ), the concentration of azide anion is controlled from 1 μM to 40 μM, and the stop concentration of azide anion is 4×10 -5 M; With the same operation but without adding azide anion, the porphyrin cage compound shown in formula (I) and methylene chloride solution are used as blank, and the UV-visible absorption spectrum of the measurement system is used.

[0051] Figure 4 It is the solution of the porphyrin cage compound shown in the formula (I) and the change situation before and after the azide anion effect; As can be seen from this figure, the maximum absorption wavelength of the porphyrin cage compound shown in the formula (I...

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Abstract

The invention discloses a porphyrin cage compound, and a preparation method and application thereof. The invention provides the porphyrin cage compound. A structural formula is shown as a formula (I). The preparation method comprises the following step of: performing 1,3-dipole cycloaddition reaction of a compound shown as a formula (II) and a compound shown as a formula (III) under the catalysis of cuprous iodide and an alkaline compound to obtain the porphyrin cage compound. According to the preparation method, the process is simple and convenient, the reaction yield is relatively high, polynitrogen anions can be identified efficiently, and the detection sensitivity is high, for example, the lower limit of detection concentration of nitrine anions in dichloromethane can reach 10 ppm; the selectivity is high, for example, the nitrine anions do not have response to other anions such as F<->, Cl<->, Br<->, I<->, SO4<2->, HSO4<->, PO4<3->, HPO4<2->, H2PO4<->, NO3<-> and the like; and a detection method can be performed by two methods, namely a nuclear magnetic resonance hydrogen spectrum and an ultraviolet spectrum, and even the nitrine anions can be determined directly and qualitatively by using naked eyes according to the change of solution colors.

Description

technical field [0001] The invention relates to a porphyrin cage compound and its preparation method and application, in particular to the application of the porphyrin cage compound in the detection of polynitrogen anions. Background technique [0002] Anions play an important role in the fields of biology, medicine, catalysis, and environmental science. In the past few decades, the design and synthesis of anion recognition systems have attracted the attention of many scientists, and a large number of excellent ion recognition systems have been successfully and applied (Y.J.Li, A.H.Flood, Angew.Chem., Int.Ed.2008 , 47, 2649-2652.Y.J.Zhao, Y.L.Li, Y.J.Li, C.S.Huang, H.B.Liu, S.W.Lai, C.M.Che, D.B.Zhu, Org.Biomol.Chem.2010, 3923-3927.). The polynitrogen anion, especially the azide anion, is a kind of anion harmful to the human body. It can combine with the cytochrome oxidase in the human body to inactivate it, thereby causing damage to the lungs, heart, and brain of the human...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/22C07D498/22G01N21/31G01N24/08
Inventor 李玉良张建宏李勇军刘辉彪
Owner INST OF CHEM CHINESE ACAD OF SCI