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CN-122010852-A - 3,3' - (1, 3-Triazole) -sulfonyl-biphenol as well as preparation method and application thereof

CN122010852ACN 122010852 ACN122010852 ACN 122010852ACN-122010852-A

Abstract

The invention relates to the technical field of liquid crystal materials, and discloses 3,3'- (1, 3-triazole) -sulfonyl-biphenol, a preparation method and application thereof, wherein 3-chloro-6 methoxy benzene sulfonyl chloride is used as a starting material, and 3,3' - (1, 3-triazole) -sulfonyl-biphenol is synthesized through azido acylation reaction, vinyl methyl formate cyclization reaction, coupling reaction and hydrolysis reaction. The novel liquid crystal material 3,3' - (1, 3-triazole) -sulfonyl-biphenol produced by the invention introduces different functional groups on the biphenol to achieve different application scenes, and compared with the traditional material, the material prepared by the invention has better conductivity, wear resistance, moisture resistance, cold resistance and the like, and breaks through the technical barrier of the application of the liquid crystal material on the market.

Inventors

  • LIN GUANGDE
  • DING AIHUA

Assignees

  • 凯密斯特(河南)医药有限公司

Dates

Publication Date
20260512
Application Date
20260130

Claims (9)

  1. 1.3, 3' - (1, 3-Triazole) -sulfonyl-biphenol characterized by the following structural formula: 。
  2. 2. a process for the preparation of 3,3' - (1, 3-triazole) -sulfonyl-biphenol according to claim 1, comprising the steps of: 3,3' - (1, 3-triazole) -sulfonyl-biphenol is synthesized by taking 3-chloro-6 methoxy benzenesulfonyl chloride as a starting material through azido acylation reaction, vinyl methyl formate cyclization reaction, coupling reaction and hydrolysis reaction.
  3. 3. The method for preparing 3,3' - (1, 3-triazole) -sulfonyl-biphenol according to claim 2, comprising the following steps: s1, reacting 3-chloro-6-methoxyl benzenesulfonyl chloride with sodium azide to generate an intermediate 3-chloro-6-methoxyl benzenesulfonyl azide with a structural formula shown in the specification, wherein the intermediate 3-chloro-6-methoxyl benzenesulfonyl azide is BP015-1; ; S2, BP015-1 reacts with methyl vinylformate to generate an intermediate BP015-2 with the structural formula shown in the specification; ; S3, BP015-2 reacts with sodium hydroxide to generate an intermediate BP015-3 with the structural formula shown in the specification; ; S4, BP015-3 reacts with hydrochloric acid to generate a target product 3,3'- (1, 3-triazole) -sulfonyl-biphenyl diphenol, and the target product 3,3' - (1, 3-triazole) -sulfonyl-biphenyl diphenol is named BP015.
  4. 4. The method for preparing 3,3' - (1, 3-triazole) -sulfonyl-biphenol according to claim 3, wherein the step S1 comprises the following steps: s1.1, adding water, sodium azide and methylene dichloride into a reaction container; S1.2, adding 3-chloro-6 methoxy benzene sulfonyl chloride to react when the temperature of a reaction container reaches minus 5 ℃, wherein the temperature in the reaction container is below 0 ℃ in the reaction process; s1.3, layering after the reaction is finished, taking the lower layer product out, washing, and obtaining the lower layer product after washing, wherein the lower layer product is methylene dichloride solution containing an intermediate BP 015-1.
  5. 5. The method for preparing 3,3' - (1, 3-triazole) -sulfonyl-biphenol according to claim 3, wherein the step S2 comprises the following steps: s2.1, adding a dichloromethane solution containing an intermediate BP015-1 and methyl vinylformate into a reaction container; s2.2, reacting for 12 hours at 30 ℃, and cooling and adding water after the reaction is finished; s2.3, standing for layering, and layering after standing for removing a lower layer product to obtain a dichloromethane solution containing an intermediate BP 015-2.
  6. 6. The method for preparing 3,3' - (1, 3-triazole) -sulfonyl-biphenol according to claim 3, wherein the step S3 comprises the following steps: S3.1, adding a dichloromethane solution containing an intermediate BP015-2, a catalyst and a reducing agent into a reaction container; s3.2, adding sodium hydroxide to react when the temperature of the reaction vessel is 40 ℃; S3.3, cooling after the reaction is finished, standing for layering, washing a lower-layer product, and obtaining a dichloromethane solution containing an intermediate BP015-3 after washing.
  7. 7. The method for preparing 3,3' - (1, 3-triazole) -sulfonyl-biphenol according to claim 6, wherein in step S3.1, the catalyst is palladium carbon and the reducing agent is formic acid.
  8. 8. The method for preparing 3,3' - (1, 3-triazole) -sulfonyl-biphenol according to claim 3, wherein the step S4 comprises the following steps: s4.1, adding methylene dichloride solution containing an intermediate BP015-3, water, hydrochloric acid and sodium iodide into a reaction container; s4.2, performing heat preservation reaction when the temperature of the reaction vessel is above 40 ℃; s4.3, after the heat preservation reaction is completed, recovering dichloromethane, and then cooling and crystallizing; s4.4, filtering and drying to obtain a target product BP015.
  9. 9. Use of 3,3' - (1, 3-triazole) -sulfonyl-biphenol according to claim 1 in liquid crystal materials.

Description

3,3' - (1, 3-Triazole) -sulfonyl-biphenol as well as preparation method and application thereof Technical Field The invention relates to the technical field of liquid crystal materials, in particular to 3,3' - (1, 3-triazole) -sulfonyl-biphenol as well as a preparation method and application thereof. Background The most widely used synthetic liquid crystal material (LCP) is polymerized biphenol, and is an organic polymer material with conductive performance. The method is mainly applied to the fields of electronics, electrics and semiconductors. With the progress of science and technology, different functional groups need to be introduced into biphenol in order to obtain liquid crystal materials with special scene application and special performance requirements. While the technical barrier for introducing other functional groups on the biphenol is the coupling of aromatic hydrocarbons. The classical arene coupling reaction is a black-type coupling method, namely, halogenated arene is coupled under the catalysis of copper powder at a high temperature of more than 150 ℃. The method has the advantages of more side reactions, low yield (60%), poor product color and luster and difficult purification. In addition, the liquid crystal material prepared from the biphenol in the prior art cannot be stably used in severe weather or places with severe environments, and is easy to damage in the severe environments. Therefore, there is a need for 3,3' - (1, 3-triazole) -sulfonyl-biphenol, and a preparation method and application thereof to solve the above technical problems. Disclosure of Invention The invention aims to overcome the technical problems in the prior art and provide 3,3' - (1, 3-triazole) -sulfonyl-biphenyl diphenol, and a preparation method and application thereof. In order to achieve the above purpose, the invention is implemented according to the following technical scheme: 3,3' - (1, 3-triazole) -sulfonyl-biphenol having the following structural formula: 。 the preparation method of the 3,3' - (1, 3-triazole) -sulfonyl-biphenol comprises the following steps: 3,3' - (1, 3-triazole) -sulfonyl-biphenol is synthesized by taking 3-chloro-6 methoxy benzenesulfonyl chloride as a starting material through azido acylation reaction, vinyl methyl formate cyclization reaction, coupling reaction and hydrolysis reaction. Preferably, the method comprises the following steps: s1, reacting 3-chloro-6-methoxyl benzenesulfonyl chloride with sodium azide to generate an intermediate 3-chloro-6-methoxyl benzenesulfonyl azide with a structural formula shown in the specification, wherein the intermediate 3-chloro-6-methoxyl benzenesulfonyl azide is BP015-1; ; the reaction equation for this reaction is as follows: 。 S2, BP015-1 reacts with methyl vinylformate to generate an intermediate BP015-2 with the structural formula shown in the specification; ; the reaction equation for this reaction is as follows: 。 S3, BP015-2 reacts with sodium hydroxide to generate an intermediate BP015-3 with the structural formula shown in the specification; ; the reaction equation for this reaction is as follows: 。 S4, BP015-3 reacts with hydrochloric acid to generate a target product 3,3'- (1, 3-triazole) -sulfonyl-biphenyl diphenol, wherein the target product 3,3' - (1, 3-triazole) -sulfonyl-biphenyl diphenol is BP015; the reaction equation for this reaction is as follows: 。 Preferably, the step S1 includes the steps of: s1.1, adding water, sodium azide and methylene dichloride into a reaction container; S1.2, adding 3-chloro-6 methoxy benzene sulfonyl chloride to react when the temperature of a reaction container reaches minus 5 ℃, wherein the temperature in the reaction container is below 0 ℃ in the reaction process; s1.3, layering after the reaction is finished, taking the lower layer product out, washing, and obtaining the lower layer product after washing, wherein the lower layer product is methylene dichloride solution containing an intermediate BP 015-1. Preferably, the step S2 includes the steps of: s2.1, adding a dichloromethane solution containing an intermediate BP015-1 and methyl vinylformate into a reaction container; s2.2, reacting for 12 hours at 30 ℃, and cooling and adding water after the reaction is finished; s2.3, standing for layering, and layering after standing for removing a lower layer product to obtain a dichloromethane solution containing an intermediate BP 015-2. Preferably, the step S3 includes the steps of: S3.1, adding a dichloromethane solution containing an intermediate BP015-2, a catalyst and a reducing agent into a reaction container; s3.2, adding sodium hydroxide to react when the temperature of the reaction vessel is 40 ℃; S3.3, cooling after the reaction is finished, standing for layering, washing a lower-layer product, and obtaining a dichloromethane solution containing an intermediate BP015-3 after washing. Preferably, in the step S3.1, the catalyst is palladium carbon and the reducing agent is formic acid.