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Azopyridines salt compound and preparation method

A technology of azopyridinium salt compound and azopyridine, which is applied in the field of azopyridinium salt compound and its preparation, and achieves the effect that the preparation method is simple and easy to be popularized and applied

Active Publication Date: 2018-01-19
BEIJING INSTITUTE OF GRAPHIC COMMUNICATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to solve some problems existing in the existing pyridinium salt compound and its preparation technology, to provide a kind of azopyridinium salt compound and its preparation method

Method used

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  • Azopyridines salt compound and preparation method
  • Azopyridines salt compound and preparation method
  • Azopyridines salt compound and preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Embodiment 1: the synthesis of compound 1d

[0038]

[0039] 1. Synthesis of intermediate 4-hydroxyazopyridine

[0040] 4.00 g (58 mmol) of sodium nitrite and 5.00 g (53 mmol) of phenol were placed in 10% (w / w) aqueous sodium hydroxide solution (20 mL), and cooled to 0°C. The above mixed solution was added dropwise to 45 mL of hydrochloric acid solution (25 mL of 11N hydrochloric acid and 20 mL of water) containing 6.00 g (64 mmol) of 4-aminopyridine. Stir under ice bath for 0.5h. Then, the pH value of the reaction mixture was adjusted to 6-7 with 10% (w / w) aqueous sodium hydroxide solution. Filtration yielded a yellow precipitate. Washed with water, recrystallized and dried to obtain a yellow solid. Yield: 38.0%.

[0041] 2. Synthesis of azopyridine derivatives (referred to as A10AzPy)

[0042] 4-Hydroxyphenylazopyridine (2.0 g, 0.1 mol), potassium iodide (0.005 g) and potassium carbonate (6.9 g, 0.005 mol) were dissolved in DMSO (20 ml) solution. A solution ...

Embodiment 2

[0045] Embodiment 2: the synthesis of compound 1a

[0046]

[0047] The reaction steps are the same as in Example 1, except that in step 2, bromononane is used instead of chlorodecane to obtain azopyridine derivatives (referred to as A9AzPy)

Embodiment 3

[0048] Embodiment 3: the generation of compound 1b

[0049]

[0050]

[0051] The reaction steps are the same as in Example 1, except that n-chlorodecane is replaced by n-bromobutane in step 2 to obtain azopyridine derivatives (referred to as A4AzPy).

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Abstract

The invention provides a preparation method of an azopyridines salt compound. The preparation method comprises the following synthesis steps: (1) enabling 4-aminopyridine and phenol to be subjected todiazo coupling reaction in the presence of nitrite to obtain an intermediate 4-hydroxyphenylazopyridine; (2) enabling the 4-hydroxyphenylazopyridine and chlorododecane or bromododecane to be subjected to etherification reaction, so as to obtain an azopyridine derivative; (3) carrying out reflowing reaction on the azopyridine derivative and 1,3,5-tribromomethyl benzene according to a certain ratioto generate the three-arm star type azopyridines salt compound. According to the preparation method provided by the invention, the azopyridines salt compound with a rapid cis-trans isomerism effect and a fluorescent light aggregation and induction effect can be prepared and has wide potential application in the fields of adjustable optical filters, adjustable multi-mode laser protection, counterfeiting prevention, optical gratings and the like and the fields of laser manipulators, liquid crystal self-adaptive optical systems and the like.

Description

technical field [0001] The invention relates to azopyridinium salt compounds and a preparation method thereof, in particular to a class of azopyridinium salt compounds prepared from 1,3,5-tribromomethylbenzene and azopyridine derivatives as raw materials and a preparation method thereof. Background technique [0002] With the development of supramolecular chemistry, the method of self-assembly to synthesize new pyridine compounds through intermolecular non-covalent bonding is more and more widely used. This method of introducing self-assembly in the structure can broaden the design scope of pyridinium salt compounds. way. Many new complexes with mesophases can be obtained through self-assembly between different donors and acceptors. As a special intermolecular force, ionic bonds have been widely used in crystal engineering, molecular recognition, supramolecular assembly, etc. . [0003] In addition to the optical activity of azopyridine derivatives, the donating property ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/76
Inventor 陈寅杰李路海曹梅娟莫黎昕窦悦刘锦缘王丹刘杏花
Owner BEIJING INSTITUTE OF GRAPHIC COMMUNICATION
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