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Alkylbenzene end group optomagnetic controllable liquid crystal compound containing Schiff base structure and preparation method thereof

A technology of liquid crystal compounds and Schiff bases, applied in chemical instruments and methods, liquid crystal materials, organic chemistry, etc., can solve problems such as system synthesis and performance research that have not been reported, and achieve the effects of mild and controllable conditions and simple preparation process.

Inactive Publication Date: 2014-07-09
XIANYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Alkylbenzene end group optomagnetic controllable liquid crystal compound containing Schiff base structure and preparation method thereof
  • Alkylbenzene end group optomagnetic controllable liquid crystal compound containing Schiff base structure and preparation method thereof
  • Alkylbenzene end group optomagnetic controllable liquid crystal compound containing Schiff base structure and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] The preparation of the photomagnetically controllable liquid crystal compound containing Schiff base structure in the terminal group of alkylbenzene comprises the following steps:

[0053] 1) Preparation of p-toluoyl chloride

[0054] Add 1.36g (0.01mol) of p-toluic acid and 2.38g (0.02mol) of thionyl chloride into the reactor, then add a mixed solution of 1.18g of DMF and 50mL of toluene, and then react at room temperature for 5 hours; The mixed solvent inside was removed under reduced pressure to obtain brown liquid p-toluyl chloride, which directly entered the next step without purification;

[0055] 2) Preparation of 4'-(4'-methylbenzoyloxy)azobenzene-4-carbaldehyde

[0056] 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 acid chloride was dissolved in dichloromethane, prepared into 40mL of a dichloromethane solution of toluoyl chloride, added dropwise under ice-b...

Embodiment 2

[0061] Example 2 (see Picture 1-1 , Figure 1-2 )

[0062] 1) Preparation of p-propylbenzoyl chloride

[0063] Take 1.64g of p-propylbenzoic 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 react at room temperature for 5h. After the reaction The mixed solvent in the reaction solution was removed under reduced pressure to obtain p-propylbenzoyl chloride, which directly entered the next step without purification;

[0064] 2) Preparation of 4'-(4'-alkylbenzoyloxy)azobenzene-4-carbaldehyde

[0065] 2.1) Preparation of p-aminobenzaldehyde

[0066]

[0067] (1) Press 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 25min, deep red Na 2 S x ;

[0068] (2) Add 27...

Embodiment 3

[0079] 1) Preparation of p-ethylbenzoyl chloride

[0080] Add 1.50g (0.01mol) of p-ethylbenzoic acid and 2.38g (0.02mol) of thionyl chloride into the reactor, then add a mixed solution of 1.18g of DMF and 50mL of toluene, and then react at room temperature for 5 hours; The mixed solvent inside was removed under reduced pressure to obtain brown liquid p-ethylbenzoyl chloride, which directly entered the next step without purification;

[0081] 2) Preparation of 4'-(4'-ethylbenzoyloxy)azobenzene-4-carbaldehyde

[0082] Take 2.26g (0.01mol) of 4'-hydroxyazobenzene-4-carbaldehyde and dissolve it in dichloromethane, then add 1.8mL of triethylamine, and then add dropwise 40mL of the product obtained in step 1) under ice-bath conditions The dichloromethane solution of p-ethylbenzoyl chloride was stirred at room temperature for 12 h. After the reaction was completed, the dichloromethane was removed under reduced pressure to obtain an orange solid; the solid was washed with 5% sodium h...

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Abstract

The invention discloses an alkylbenzene end group optomagnetic controllable liquid crystal compound containing a Schiff base structure and a preparation 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 preparation method of the compound comprises the following steps that: alkyl benzoic acid is subjected to acylating chlorination by thionyl chloride; a product generated during the acylating chlorination and 4'-hydroxyazobenzene-4-formaldehyde are in esterification reaction; and a product generated during the esterification reaction and 4-NH2-TEMPO(4-amino-2,2,6,6-tetramethyl piperidine-1-oxygen radical are in Schiff base reaction, so as to obtain the alkylbenzene 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 at an alkylbenzene end group and a preparation 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 performa...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D211/94C09K19/34
Inventor 郑敏燕魏永生王珊尚永辉耿薇
Owner XIANYANG NORMAL UNIV