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CN-122010972-A - Photosensitive chiral dopant and preparation method and application thereof

CN122010972ACN 122010972 ACN122010972 ACN 122010972ACN-122010972-A

Abstract

The application relates to the technical field of synthesis of photosensitive organic matters, and discloses a photosensitive chiral dopant, a preparation method and application thereof. The molecular formula of the photosensitive chiral dopant is shown as a formula X or a formula Y: The preparation method comprises the steps of dissolving isosorbide, p-hydroxybenzoic acid and an acid catalyst in a nonpolar organic solvent, carrying out esterification reaction, carrying out aftertreatment to obtain an intermediate, dissolving the intermediate, 9-anthranilic acid and the acid catalyst in the nonpolar organic solvent, carrying out esterification reaction, and carrying out aftertreatment to obtain the photosensitive chiral dopant X or the photosensitive chiral dopant Y. The photosensitive chiral dopant containing anthracene structure can realize light reversible response color change in a certain temperature range and a certain wavelength by being blended with other chiral agents and liquid crystal and dispersed in a polymer. The preparation process of the photosensitive chiral dopant is simple, and the raw materials are low in price and easy to obtain.

Inventors

  • YANG YUZHAO
  • XIONG WENJUN
  • CHEN XUDONG
  • WU JING
  • WU BOYU
  • CHEN JIAXI
  • Wang Ruilei
  • WANG CHENG

Assignees

  • 广东工业大学
  • 化学与精细化工广东省实验室揭阳分中心

Dates

Publication Date
20260512
Application Date
20260107

Claims (10)

  1. 1. A photosensitive chiral dopant having a formula of formula X or formula Y: 。
  2. 2. The photosensitive chiral dopant of claim 1, which is synthesized by the process comprising: ; ; Or: 。
  3. 3. A method of preparing a photoactive chiral dopant as claimed in claim 2, comprising: S1, dissolving isosorbide, p-hydroxybenzoic acid and an acid catalyst in a nonpolar organic solvent, carrying out esterification reaction, and carrying out aftertreatment to obtain an intermediate; s2, dissolving the intermediate, 9-anthracene carboxylic acid and an acid catalyst in a nonpolar organic solvent, performing esterification reaction, and performing aftertreatment to obtain the photosensitive chiral dopant X or the photosensitive chiral dopant Y.
  4. 4. The production method according to claim 3, wherein the acid catalyst comprises any one of concentrated hydrochloric acid, concentrated sulfuric acid, phosphoric acid, boric acid, benzenesulfonic acid, or p-toluenesulfonic acid; the nonpolar organic solvent comprises any one of benzene, toluene, xylene, trimethylbenzene, carbon tetrachloride or cyclohexane.
  5. 5. The method according to claim 3, wherein the esterification reaction is carried out at a temperature of 120 to 150 ℃ for 24 to 48 hours.
  6. 6. The method according to claim 3, wherein the molar ratio of isosorbide, parahydroxybenzoic acid and acid catalyst in S1 is 1:2-2.2:0.3-0.5.
  7. 7. The preparation method according to claim 3, wherein in S2, when the molar ratio of the intermediate, 9-anthracene carboxylic acid and the acid catalyst is 1:2-2.2:0.3-0.5, the product is a photosensitive chiral dopant X; When the molar ratio of the intermediate to the 9-anthracene carboxylic acid to the acid catalyst is 1-1.2:1:0.3-0.5, the product is the photosensitive chiral dopant Y.
  8. 8. A method of preparation according to claim 3, wherein the post-treatment in S1 comprises: Evaporating to remove solvent after esterification, washing the residue with alkaline solution to neutrality, filtering, drying, and performing silica gel column chromatography to obtain intermediate; The post-processing in S2 includes: And after the esterification reaction, collecting a solid phase, washing the solid phase to be neutral by using an alkaline solution, washing, drying, and then carrying out silica gel column chromatography to obtain the photosensitive chiral dopant X or the photosensitive chiral dopant Y.
  9. 9. The method of claim 8, wherein the alkaline solution comprises a sodium carbonate solution or a sodium bicarbonate solution; the eluent of the silica gel column chromatography in the S1 is a mixture of ethyl acetate and petroleum ether according to the volume ratio of 1-3:1; in S2, the eluent of the silica gel column chromatography is a mixture of dichloromethane and petroleum ether with the volume ratio of 10-6:1.
  10. 10. Use of a photoactive chiral dopant as defined in claim 1 in the preparation of a patterned material.

Description

Photosensitive chiral dopant and preparation method and application thereof Technical Field The application relates to the technical field of synthesis of photosensitive organic matters, in particular to a photosensitive chiral dopant, a preparation method and application thereof. Background Cholesteric Liquid Crystals (CLCs) are represented as smart soft substances with great potential, and have recently led to extensive and continuous research in the field of material science. After chiral dopants are introduced into a nematic Liquid Crystal (LC) matrix, the original linearly aligned liquid crystal molecular chains are regularly twisted, and a periodically spirally aligned layered structure is formed, so that cholesteric liquid crystals can be obtained. In cholesteric liquid crystal, the pitch (pitch) parameter of the helical structure not only depends on the concentration and molecular structure of chiral dopants, but also can be dynamically adjusted along with the change of environmental conditions, and when external stimulus acts on a system, the change of intermolecular acting force can cause the change of the helical parameter, so that the macroscopic properties of the liquid crystal material such as optics, electricity and the like are obviously changed. The structure endows the cholesteric liquid crystal with highly sensitive environmental response characteristics, so that the cholesteric liquid crystal can generate obvious change to various external stimuli such as light, heat, electric field, mechanical stress and the like. Among the many environmental stimuli, light has particular advantages due to its availability of tunable intensity, polarization and wavelength, and photoresponsive cholesteric liquid crystals as photochromic materials have shown excellent research value in the fields of anti-counterfeiting, optical masks, optical switching molecular devices, and the like. Currently, various optical switches have been used as dopants for light-responsive cholesteric liquid crystals, such as azobenzene, spiropyran, diarylethene, hydrazone, and the like. However, the above optical switch has the problems of complex design and synthesis, high raw material cost, difficult acquisition, poor stability and the like, and the defects influence the practical application of the photochromic material in various fields. Disclosure of Invention The application provides a photosensitive chiral dopant, a preparation method and application thereof, and aims to solve the technical problems of complex design and synthesis process, high raw material cost and poor stability of the existing photosensitive dopant. In order to achieve the above purpose, the present application is realized by the following technical scheme. In a first aspect of the present application, there is provided a photosensitive chiral dopant having a formula represented by formula X or formula Y: 。 Preferably, the synthesis process of the photosensitive chiral dopant is as follows: ; Or: 。 In a second aspect of the present application, there is provided a method for preparing the above photosensitive chiral dopant, comprising: S1, dissolving isosorbide, p-hydroxybenzoic acid and an acid catalyst in a nonpolar organic solvent, carrying out esterification reaction, and carrying out aftertreatment to obtain an intermediate; s2, dissolving the intermediate, 9-anthracene carboxylic acid and an acid catalyst in a nonpolar organic solvent, performing esterification reaction, and performing aftertreatment to obtain the photosensitive chiral dopant X or the photosensitive chiral dopant Y. Preferably, the acid catalyst comprises any one of concentrated hydrochloric acid, concentrated sulfuric acid, phosphoric acid, boric acid, benzenesulfonic acid or p-toluenesulfonic acid; the nonpolar organic solvent comprises any one of benzene, toluene, xylene, trimethylbenzene, carbon tetrachloride or cyclohexane. Preferably, the temperature of the esterification reaction is 120-150 ℃ and the reaction time is 24-48 h. Preferably, the molar ratio of the isosorbide to the p-hydroxybenzoic acid to the acid catalyst in the S1 is 1:2-2.2:0.3-0.5. Preferably, in S2, when the molar ratio of the intermediate to the 9-anthracene carboxylic acid to the acid catalyst is 1:2-2.2:0.3-0.5, the product is a photosensitive chiral dopant X; When the molar ratio of the intermediate to the 9-anthracene carboxylic acid to the acid catalyst is 1-1.2:1:0.3-0.5, the product is the photosensitive chiral dopant Y. Preferably, the post-processing in S1 includes: Evaporating to remove solvent after esterification, washing the residue with alkaline solution to neutrality, filtering, drying, and performing silica gel column chromatography to obtain intermediate; The post-processing in S2 includes: And after the esterification reaction, collecting a solid phase, washing the solid phase to be neutral by using an alkaline solution, washing, drying, and then carrying out silica gel column chromat