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Dinaphthalene azobenzene ring-type photosensitive chiral molecule and preparation method and application thereof

A technology of binaphthylazobenzene and chiral molecules, which is applied in the field of preparation of light-responsive materials and achieves the effect of good compatibility

Active Publication Date: 2019-05-28
HEFEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Compared with Azo-o-Bi chiral agent molecules, by introducing rigid substituents at the 6,6' position, it can improve its compatibility with liquid crystal molecules and effectively promote the transfer of chirality. At present, there are few A Cyclic Photosensitive Chiral Agent Molecule with Substituents at 6,6' Positions

Method used

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  • Dinaphthalene azobenzene ring-type photosensitive chiral molecule and preparation method and application thereof
  • Dinaphthalene azobenzene ring-type photosensitive chiral molecule and preparation method and application thereof
  • Dinaphthalene azobenzene ring-type photosensitive chiral molecule and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] The specific synthesis steps of R-binaphthazobenzene photosensitive cyclic chiral molecules are as follows:

[0036] 1.1 Preparation of intermediate 1

[0037] Dissolve (R)-6,6'dibromo-1,1'-bi-2-naphthol (1.0g, 2.3mmol), potassium carbonate (1.1g, 7.9mmol), potassium iodide (0.1g, 0.7mmol) In N,N-dimethylformamide, after stirring the reaction at 100°C for 20min, add 2-(2-chloroethoxy)ethanol (1.0g, 7.9mmol) and continue the reaction at 100°C 24h. After the reaction was completed and cooled to room temperature, the reaction solution was poured into ice water for dilution, extracted three times with ethyl acetate and saturated saline, dried over anhydrous sodium sulfate and subjected to silica gel column chromatography to obtain intermediate 1, whose structural formula is as follows:

[0038]

[0039] 1.2 Preparation of Intermediate 2

[0040] Weigh the intermediate 1 (1g, 1.6mmol) and 4-pentyloxybiphenylboronic acid (1.1g, 3.84mmol) and dissolve it in 1,4-dioxane, ...

Embodiment 2

[0051] Changes of Twisting Force Constant of Cholesteric Liquid Crystals

[0052] Add 0.002 g of the binaphthazobenzene photosensitive cyclic chiral molecule to 0.100 g of liquid crystal, heat to the clearing point for 2 hours, cool to room temperature, and then slowly pour into a wedge cell (tanθ=0.01). After standing for a period of time, the change of the thread pitch was measured by polarizing microscope under the illumination of 365nm and 440nm respectively, and the corresponding thread pitch changed from 17.5 μm to 20.7 μm and finally to 19.5 μm.

Embodiment 3

[0054] Compatibility determination

[0055] The Teas solubility parameters of the binaphthazobenzene photosensitive cyclic chiral molecule, the Azo-o-Bi chiral agent molecule and the liquid crystal host E7 molecule were calculated respectively, and the differences between the two kinds of chiral agent molecules and the liquid crystal host were compared. Teas parameter difference (Δf), in general, the compatibility between chiral agent molecules and liquid crystal molecules decreases with the increase of Δf value. By calculation, the Δf value between the Azo-o-Bi chiral agent molecule and the liquid crystal host molecule is 0.17, and the Δf value between the binaphthazobenzene photosensitive cyclic chiral molecule and the liquid crystal host molecule is reduced to 0.15, improving the The compatibility with the liquid crystal host molecules is improved.

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Abstract

The invention discloses a dinaphthalene azobenzene ring-type photosensitive chiral molecule and a preparation method and application thereof. The preparation method comprises the steps that 6,6'dibromo-1,1'-bi-2-naphthol, potassium carbonate, potassium iodide and 2-(2-chloroethoxy)ethanol are dissolved in N,N-dimethylformamide, thus a midbody 1 is obtained, the midbody 1 and [4'-(pentyloxy)[1,1'-biphenyl]-4-yl]boronic acid are dissolved in 1,4-dioxane to react with a potassium carbonate aqueous solution and tetrakispalladium to obtain a midbody 2, the midbody 2 is dissolved through dichloromethane, and then triethylamine, 4-dimethylaminopyridine and paratoluensulfonyl chloride are added and react to obtain a midbody 3; and cesium carbonate is added into the midbody 3, 2,2'-dihydroxyazobenzene and dibenzo-18-crown ether-6 under the nitrogen atmosphere for reacting, and thus a target product T is obtained. The dinaphthalene azobenzene ring-type photosensitive chiral molecule is easy to synthesize and good in stability, the screw pitch of a cholesteric liquid crystal can be adjusted and controlled through photoinduced cis-trans isomerization, and good compatibility between the dinaphthalene azobenzene ring-type photosensitive chiral molecule and liquid crystal molecules is achieved.

Description

technical field [0001] The invention belongs to binaphthazobenzene photosensitive cyclic chiral molecules, a preparation method and application thereof, and belongs to the field of photoresponsive material preparation. Background technique [0002] Azo compounds are an important class of organic compounds widely used in dyes and analytical reagents. Azo compounds have important research value in the fields of optical information storage materials, nonlinear optical materials, liquid crystal materials, bioactive light regulation and nanomaterials. Azobenzene-containing compounds have become a frontier field of functional materials research due to their unique photoresponsive properties, showing broad prospects for development. Binaphthalene compounds are biaryl compounds with axial asymmetry that have been studied more in recent years. After connecting the 1 positions of the two naphthalene rings and introducing substituents at the 2,2' and 6,6' It becomes a chiral compound...

Claims

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Application Information

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IPC IPC(8): C07F5/02C07C43/225C07C41/16G01N21/84
Inventor 陆红波周梦怡郑安东李志远韦成
Owner HEFEI UNIV OF TECH
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