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Alkyl biphenyl end group optomagnetic controllable liquid crystal compound containing Schiff base structure and synthetic method thereof

A technology for alkyl biphenyl terminal groups and liquid crystal compounds, which is applied in the field of optomagnetically controllable liquid crystal compounds containing Schiff base structures in alkyl biphenyl terminal groups and its synthesis, and can solve problems such as system synthesis and performance research that have not been reported. , to achieve the effect of mild and controllable synthesis process conditions and simple preparation process

Inactive Publication Date: 2013-01-02
XIANYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no report on the systematic synthesis and performance research of small molecule liquid crystals with both magnetic groups and photosensitive groups in the molecule.

Method used

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  • Alkyl biphenyl end group optomagnetic controllable liquid crystal compound containing Schiff base structure and synthetic method thereof
  • Alkyl biphenyl end group optomagnetic controllable liquid crystal compound containing Schiff base structure and synthetic method thereof
  • Alkyl biphenyl end group optomagnetic controllable liquid crystal compound containing Schiff base structure and synthetic method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0048] The preparation of the optomagnetically controllable liquid crystal compound containing Schiff base structure in the terminal group of alkyl biphenyl comprises the following steps:

[0049] 1) Preparation of 4'-methylbiphenyl-4-formyl chloride

[0050] Take 2.12g (0.01mol) of 4'-methylbiphenyl-4-carboxylic acid and 2.38g (0.02mol) of thionyl chloride respectively in the reactor, and then add a mixed solvent of 1.18g of DMF and 50mL of toluene , and then reacted at room temperature for 5 hours. After the reaction, the mixed solvent in the reaction solution was removed under reduced pressure to obtain a brown liquid 4'-methylbiphenyl-4-formyl chloride, which was directly entered into the next step without purification;

[0051] 2) Preparation of 4'-(4'-(4'-methylphenyl)benzoyloxy)azobenzene-4-carbaldehyde

[0052] Take 2.26g (0.01mol) of 4'-hydroxyazobenzene-4-carbaldehyde dissolved in dichloromethane and add to the reactor, then add 1.8mL of triethylamine; Dissolve met...

Embodiment 2

[0056] Embodiment 2 (see Figure 1-1, Figure 1-2 )

[0057] 1) Preparation of 4'-ethylbiphenyl-4-formyl chloride

[0058] Take 2.40g of 4'-ethylbiphenyl-4-carboxylic acid and 2.38g (0.02mol) of thionyl chloride respectively in the reactor, then add a mixed solvent of 1.18g of DMF and 50mL of toluene, and then After the reaction was completed, the mixed solvent in the reaction solution was removed under reduced pressure to obtain a brown liquid 4'-ethylbiphenyl-4-formyl chloride, which was directly entered into the next step without purification;

[0059] 2) Preparation of 4'-(4'-(4'-ethylphenyl)benzoyloxy)azobenzene-4-carbaldehyde

[0060] 2.1) Preparation of p-aminobenzaldehyde

[0061]

[0062] (1) Add 12g of Na 2 Add S and 12g of NaOH to 200mL water to form a mixed solution, then filter; add the filtrate to a 500mL three-necked flask, stir and heat to 65°C, then add 5.4g of sulfur powder, then continue stirring, heat up to 100°C through an oil bath, and then boil 25...

Embodiment 3

[0074] 1) Preparation of 4'-propylbiphenyl-4-formyl chloride

[0075] Take 2.40g (0.01mol) of 4'-propylbiphenyl-4-carboxylic acid and 2.38g (0.02mol) of thionyl chloride respectively in the reactor, and then add a mixed solvent of 1.18g of DMF and 50mL of toluene , and then reacted at room temperature for 5 hours. After the reaction, the mixed solvent in the reaction solution was removed under reduced pressure to obtain a brown liquid 4'-propylbiphenyl-4-formyl chloride, which was directly proceeded to the next step without purification;

[0076] 2) Preparation of 4'-(4'-(4'-propylphenyl)benzoyloxy)azobenzene-4-carbaldehyde

[0077] Take 2.26g (0.01mol) of 4'-hydroxyazobenzene-4-carbaldehyde dissolved in dichloromethane and add to the reactor, then add 1.8mL of triethylamine; the 4'-propane prepared in step 1) Propylbiphenyl-4-formyl chloride was dissolved in dichloromethane to prepare 40mL of 4'-propylbiphenyl-4-formyl chloride in dichloromethane solution, which was added dr...

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Abstract

The invention discloses an alkyl biphenyl end group optomagnetic controllable liquid crystal compound containing a Schiff base structure and a synthetic method thereof. The compound is 2,2,6,6-tetramethyl-4-(4-(4-(4-alkylbenzene acyl oxygen) benzene azo) benzylidene imino group) piperidine oxygen radical. The synthetic method of the compound comprises the following steps that: 4'-alkyl biphenyl-4 formic acid is subjected to acylating chlorination by thionyl chloride and then reacts with 4'-hydroxyazobenzene-4-formaldehyde in an esterification way; and a product generated during the esterification reaction is subjected to Schiff base reaction with 4-NH2-TEMPO (4-amino-2,2,6,6-tetramethyl piperidine-1-oxygen radical, so as to obtain the alkyl biphenyl end group optomagnetic controllable liquid crystal compound containing the Schiff base structure. Structurally, the compound integrates the liquid crystalline property, the magnetism and the light sensitivity into a whole, and the liquid crystalline property transform of materials can be realized by light control and magnetic control.

Description

technical field [0001] The invention belongs to the technical field of material chemistry and fine chemical industry, and relates to an optomagnetically controllable liquid crystal compound containing a Schiff base structure in an alkyl biphenyl terminal group and a synthesis method thereof. Background technique [0002] As a special state of matter, liquid crystal is widely used in the fields of displays, detectors, sensors, and chemical analysis and detection, and its order can also be used to realize the separation and purification of substances. Liquid crystal molecules have optical activity, and liquid crystal molecules with a rod-like or disc-like structure can be arranged in an orderly manner in an electric field, thereby realizing liquid crystal display or other application performance. [0003] Scientists from various countries are constantly exploring the retention of molecular liquid crystallinity, and expect to synthesize multifunctional materials with better per...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/94C09K19/34
Inventor 魏永生郑敏燕郭乃妮张萍古元梓
Owner XIANYANG NORMAL UNIV