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Azopyridinium salt compound and preparation method
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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: 2021-04-06
BEIJING INSTITUTE OF GRAPHIC COMMUNICATION
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[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
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Embodiment 1
[0036] Embodiment 1: the synthesis of compound 1c
[0037]
[0038] 1. Synthesis of intermediate 4-hydroxyazopyridine
[0039] 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%.
[0040] 2. Synthesis of azopyridine derivatives (referred to as A10AzPy)
[0041] 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
[0044] Embodiment 2: the synthesis of compound 1b
[0045]
[0046] The reaction steps are the same as in Example 1, except that in step 2, bromononane is used instead of chlorodecane to obtain an azopyridine derivative (referred to as A9AzPy).
Embodiment 3
[0047] Embodiment 3: the generation of compound 1a
[0048]
[0049] 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).
[0050] Explanation of each drawing (taking 10TBMB as an example)
[0051] Figure 1 In deuterated chloroform, as shown in figure (a), the positions a and c in the 10TBMB H NMR spectrum are obviously shifted to the lower field direction than the raw material A10AzPy, and the positions b and d are obviously moved to the higher field than the raw material A10AzPy direction movement, indicating that the raw material A10AzPy interacted with 1,3,5-tribromomethylbenzene. Figure (b) is the NMR of pyridinium salts in different proportions. The preliminary results are analyzed as follows: 4.39ppm is the peak of methyl hydrogen on the bromomethyl group that does not participate in the reaction on 1,3,5-3 bromomethylbenzene, 1: 1. When the ra...
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Abstract
The invention provides a method for preparing an azopyridinium salt compound, the synthesis comprising the following steps: (1) 4-aminopyridine and phenol undergo a diazo coupling reaction in the presence of nitrite to obtain an intermediate 4-hydroxy Phenyl azopyridine; (2) 4-Hydroxy phenyl azopyridine is etherified with chlorodecane or bromodecane to generate azopyridine derivatives. (3) Azopyridine derivatives and 1,3,5-tribromomethylbenzene are condensed and refluxed in a certain proportion to generate a three-arm star-shaped azopyridinium salt compound. The application can prepare azopyridinium salt compounds with rapid cis-trans isomerization effect and aggregation-induced fluorescence effect, which can be used in adjustable optical filters, adjustable multi-mode laser protection, anti-counterfeiting, grating and other fields, as well as laser control It has broad potential applications in fields such as devices and liquid crystal adaptive optics systems.
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 ...
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