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Photosensitive chiral macrocyclic molecule and preparation method and application thereof

A macrocyclic molecule, chiral technology, applied in the field of photoresponsive material preparation

Active Publication Date: 2015-04-08
黄山市开发投资集团有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are few molecules that can control the complexation ability of molecules by light

Method used

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  • Photosensitive chiral macrocyclic molecule and preparation method and application thereof
  • Photosensitive chiral macrocyclic molecule and preparation method and application thereof
  • Photosensitive chiral macrocyclic molecule and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1: Preparation of R-type binaphthyl photosensitive chiral macrocyclic molecule

[0039] a). Dissolve 5.000g (0.0472mol) of diethylene glycol, 4.774g (0.1038mol) of sodium hydroxide and 19.72g (0.1038mol) of p-toluenesulfonyl chloride in 40ml tetrahydrofuran under the protection of nitrogen, and stir at room temperature for 10h , the product was recrystallized in distilled water, washed and dried to obtain white solid powder Intermediate 1, its structural formula is as follows:

[0040]

[0041] NMR spectrum such as Figure 7 , 1H NMR (300MHz, CDCl3) data: δ (ppm) 2.428 (s, 6H), 3.588 (t, J=4.8Hz, 4H), 4.035 (t, J=4.8Hz, 4H), 7.319 (d, J = 8.1 Hz, 4H), 7.774 (d, J = 8.1 Hz, 4H).

[0042]b). Take 5.8g (0.014mol) of the intermediate 1, 1g (0.0047mol) of o-dihydroxyazobenzene, 4.56g (0.014mol) of cesium carbonate and 0.504g (0.0014mol) of dibenzo-octadecacrown Dissolve in 50ml of N,N-dimethylformamide, stir at 80°C for 13h under nitrogen atmosphere, add ethyl ...

Embodiment 2

[0049] Example 2: Photoresponsive complexation and release of chiral ammonium salts

[0050] Take 2 mg of the target product to form a concentration of 2×10 -5 mol / L tetrahydrofuran solution, the solution was treated in the dark at 55°C for 8 hours, exposed to 365nm light, and the circular dichroism spectrum and UV-visible spectrum of the substance were measured at different exposure times. image 3 The middle square line is the circular dichroism spectrum of the solution after long-time 365nm ultraviolet exposure, and the hollow triangle line is the circular dichroism spectrum of the solution after long-time 440nm exposure. changes happened, Figure 4 The UV-Vis spectrum graph lines under different illumination times have been marked in the figure. With the increase of the exposure time, the UV absorption at 365nm decreases, and the UV absorption at 440nm increases, indicating that the molecule has the property of light response. Add different concentrations of L-alanine et...

Embodiment 3

[0052] Example 3: Changes in Twisting Force Constant of Cholesteric Liquid Crystals

[0053] Take 0.1g of liquid crystal and add 0.002g of the target product, heat it to the clearing point of the liquid crystal on a hot stage, keep the temperature at a constant temperature for 1 hour, make it fully mixed, and then add it into a wedge-shaped liquid crystal box. The wedge-shaped liquid crystal cell was observed under a polarizing microscope, and the pitch length of the liquid crystal was measured to be 2065 μm. The liquid crystal device is alternately illuminated with 365nm and 440nm, and the measured pitch length is 1689μm and 2356μm. Figure 5 .

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Abstract

The invention discloses a photosensitive chiral macrocyclic molecule and a preparation method and application thereof, belonging to the field of preparation of photoresponsive materials. The preparation method for the photosensitive chiral macrocyclic molecule adopts the following steps: a) reacting oligomeric ethylene glycol, sodium hydroxide and p-toluenesulfonyl chloride in a tetrahydrofuran solvent in an inert atmosphere so as to obtain an intermediate 1; b) dissolving the intermediate 1, cesium carbonate and dibenzo-18-crown-6 in an N-N dimethylformamide solvent and carrying out a reaction in an inert atmosphere so as to obtain an intermediate 2; and c) dissolving the intermediate 2, chiral binaphthol compounds, cesium carbonate and dibenzo-18-crown-6 in the N-N dimethylformamide solvent and carrying out a reaction in an inert atmosphere so as to obtain a target product. The photosensitive chiral macrocyclic molecule provided by the invention has the advantages of easy synthesis, good stability, ability of selective complexation of chiral ammonium salt and capability of realizing complexation and release of chiral ammonium salt through an azo cis-trans isomerization behavior.

Description

technical field [0001] The invention relates to a photosensitive chiral macrocyclic molecule and its preparation method and application, belonging 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 application 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 biaromatic compounds with axial asymmetry that have been studied more in recent years. The naphthalene ring itself has no chirality, but when two naphthalene rings are connected at the 1 position and two substituents are introduced at t...

Claims

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Application Information

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IPC IPC(8): C07D273/08G01N21/33G01N21/25C09K19/54
Inventor 陆红波吕国强贺晓悦谢欣燕邱龙臻吴宗铨
Owner 黄山市开发投资集团有限公司
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