A kind of reactive azobenzene main side chain liquid crystal compound and its preparation method and application

Abstract

The invention belongs to the technical field of functional materials, and discloses a reactive azobenzene main side chain liquid crystal compound and its preparation method and application, specifically 2-(((6-(4-(phenyldiazenyl)benzene) Oxygen) hexyl) oxy) carbonyl)-1,4-phenylene "bis (4-(allyloxy) benzoate) compound. The liquid crystal compound structural formula of the present invention is as follows: the present invention is On the basis of ‑N=N‑reversible photodenaturation in nitrogen liquid crystals, a reactive double bond functional group is introduced, and the synthesized reactive azobenzene main side chain liquid crystal compound not only has excellent liquid crystal properties, but also because of its reversible The reacted double bond can form a self-supporting material, which has broad application prospects in optical storage, optical holography, optical information processing and other fields.

Description

technical field

[0001] The invention belongs to the technical field of functional materials, in particular to a reactive azobenzene main side chain liquid crystal compound and its preparation method and application, specifically 2-(((6-(4-(phenyldiazenyl)benzene) Oxy)hexyl)oxy)carbonyl)-1,4-phenylene"bis(4-(allyloxy)benzoate) compounds. Background technique

[0002] The azophenyl group is a class of optically active functional groups. The N=N double bond in the molecule can undergo the isomerization transformation of Trans→cis and cis→trans under the action of light and heat (see the transformation schematic diagram in figure 1 ), so azo compounds have both cis and trans isomers. Among them, the trans structure is more stable than the cis structure, which is conducive to the orderly orientation of molecules, and has unique photo-induced orientation characteristics. The unique properties of azo compounds make them widely used in liquid crystal materials, optical information...

Examples

Embodiment 1

[0062] A reactive type azobenzene main side chain liquid crystal compound, prepared by the method comprising the following steps, the structural formula of the liquid crystal compound of the present invention is as follows: figure 2 As shown, the synthetic route is as image 3 Shown:

[0063] (1) Dissolve 17.52 parts by mass of 1,6-dibromohexane, 0.36 parts by mass of potassium iodide in 30 parts by volume of acetone, heat up to 60°C, add 12.45 parts by mass of anhydrous potassium carbonate, stir for 0.5h, then Under nitrogen protection, 11.89 parts by mass of 4-hydroxyazobenzene in acetone (200 parts by volume) was slowly added to the mixture through a constant pressure funnel, and stirred for 48 hours. After confirming the complete reaction of 4-hydroxybiazobenzene by TLC, the salt in the reaction mixture was removed by filtration, the filtrate was concentrated to about 50 parts by volume, and then poured into absolute ethanol to precipitate yellow crystals. The crystals ...

Embodiment 2

[0069] A reactive azobenzene main side chain liquid crystal compound is prepared by a method comprising the following steps:

[0070] (1) Dissolve 29.2 parts by mass of 1,6-dibromohexane and 0.6 parts by mass of potassium iodide in 30 parts by volume of acetone, heat up to 60°C, add 16.6 parts by mass of anhydrous potassium carbonate, stir for 0.5h, and then Under nitrogen protection, 11.89 parts by mass of 4-hydroxyazobenzene in acetone (200 parts by volume) was slowly added to the mixture through a constant pressure funnel, and stirred for 48 hours. After confirming the complete reaction of 4-hydroxybiazobenzene by TLC, the salt in the reaction mixture was removed by filtration, the filtrate was concentrated to about 50 parts by volume, and then poured into absolute ethanol to precipitate yellow crystals. The crystals were collected by filtration, washed 3 times with water (200 parts by volume), and dried in a vacuum oven at 50° C. for 24 hours to obtain 4-(((6-bromohexyl)ox...

Embodiment 3

[0076] A reactive azobenzene main side chain liquid crystal compound is prepared by a method comprising the following steps:

[0077] (1) Dissolve 17.52 parts by mass of 1,6-dibromohexane, 0.36 parts by mass of potassium iodide in 30 parts by volume of acetone, heat up to 60°C, add 12.45 parts by mass of anhydrous potassium carbonate, stir for 1.0h, then Under nitrogen protection, 11.89 parts by mass of 4-hydroxyazobenzene in acetone (200 parts by volume) was slowly added to the mixture through a constant pressure funnel, and stirred for 50 h. After confirming the complete reaction of 4-hydroxybiazobenzene by TLC, the salt in the reaction mixture was removed by filtration, the filtrate was concentrated to about 50 parts by volume, and then poured into absolute ethanol to precipitate yellow crystals. The crystals were collected by filtration, washed 3 times with water (200 parts by volume), and dried in a vacuum oven at 50° C. for 24 hours to obtain 4-(((6-bromohexyl)oxy)phenyl...

technical field

[0001] The invention belongs to the technical field of functional materials, in particular to a reactive azobenzene main side chain liquid crystal compound and its preparation method and application, specifically 2-(((6-(4-(phenyldiazenyl)benzene) Oxy)hexyl)oxy)carbonyl)-1,4-phenylene"bis(4-(allyloxy)benzoate) compounds. Background technique

[0002] The azophenyl group is a class of optically active functional groups. The N=N double bond in the molecule can undergo the isomerization transformation of Trans→cis and cis→trans under the action of light and heat (see the transformation schematic diagram in figure 1 ), so azo compounds have both cis and trans isomers. Among them, the trans structure is more stable than the cis structure, which is conducive to the orderly orientation of molecules, and has unique photo-induced orientation characteristics. The unique properties of azo compounds make them widely used in liquid crystal materials, optical information...

Examples

Embodiment 1

[0062] A reactive type azobenzene main side chain liquid crystal compound, prepared by the method comprising the following steps, the structural formula of the liquid crystal compound of the present invention is as follows: figure 2 As shown, the synthetic route is as image 3 Shown:

[0063] (1) Dissolve 17.52 parts by mass of 1,6-dibromohexane, 0.36 parts by mass of potassium iodide in 30 parts by volume of acetone, heat up to 60°C, add 12.45 parts by mass of anhydrous potassium carbonate, stir for 0.5h, then Under nitrogen protection, 11.89 parts by mass of 4-hydroxyazobenzene in acetone (200 parts by volume) was slowly added to the mixture through a constant pressure funnel, and stirred for 48 hours. After confirming the complete reaction of 4-hydroxybiazobenzene by TLC, the salt in the reaction mixture was removed by filtration, the filtrate was concentrated to about 50 parts by volume, and then poured into absolute ethanol to precipitate yellow crystals. The crystals ...

Embodiment 2

[0069] A reactive azobenzene main side chain liquid crystal compound is prepared by a method comprising the following steps:

[0070] (1) Dissolve 29.2 parts by mass of 1,6-dibromohexane and 0.6 parts by mass of potassium iodide in 30 parts by volume of acetone, heat up to 60°C, add 16.6 parts by mass of anhydrous potassium carbonate, stir for 0.5h, and then Under nitrogen protection, 11.89 parts by mass of 4-hydroxyazobenzene in acetone (200 parts by volume) was slowly added to the mixture through a constant pressure funnel, and stirred for 48 hours. After confirming the complete reaction of 4-hydroxybiazobenzene by TLC, the salt in the reaction mixture was removed by filtration, the filtrate was concentrated to about 50 parts by volume, and then poured into absolute ethanol to precipitate yellow crystals. The crystals were collected by filtration, washed 3 times with water (200 parts by volume), and dried in a vacuum oven at 50° C. for 24 hours to obtain 4-(((6-bromohexyl)ox...

Embodiment 3

[0076] A reactive azobenzene main side chain liquid crystal compound is prepared by a method comprising the following steps:

[0077] (1) Dissolve 17.52 parts by mass of 1,6-dibromohexane, 0.36 parts by mass of potassium iodide in 30 parts by volume of acetone, heat up to 60°C, add 12.45 parts by mass of anhydrous potassium carbonate, stir for 1.0h, then Under nitrogen protection, 11.89 parts by mass of 4-hydroxyazobenzene in acetone (200 parts by volume) was slowly added to the mixture through a constant pressure funnel, and stirred for 50 h. After confirming the complete reaction of 4-hydroxybiazobenzene by TLC, the salt in the reaction mixture was removed by filtration, the filtrate was concentrated to about 50 parts by volume, and then poured into absolute ethanol to precipitate yellow crystals. The crystals were collected by filtration, washed 3 times with water (200 parts by volume), and dried in a vacuum oven at 50° C. for 24 hours to obtain 4-(((6-bromohexyl)oxy)phenyl...

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