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Laterally tetrafluoro-substituted dibenzoheterocyclic compound and preparation method thereof

A technology of heterocyclic compounds and compounds, applied in the field of materials, can solve the problems of small absolute value of dielectric anisotropy, difficult to improve the response speed, etc., and achieve large negative dielectric anisotropy, high product yield and purity, and easy operation. simple effect

Active Publication Date: 2017-05-24
SHAANXI UNIV OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The dielectric anisotropy of such compounds with dielectric anisotropy currently used is generally around -5, and the dielectric anisotropy of mixed liquid crystals used for display is generally around -3.5, and the absolute value of dielectric anisotropy Smaller, making it difficult to improve responsiveness

Method used

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  • Laterally tetrafluoro-substituted dibenzoheterocyclic compound and preparation method thereof
  • Laterally tetrafluoro-substituted dibenzoheterocyclic compound and preparation method thereof
  • Laterally tetrafluoro-substituted dibenzoheterocyclic compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Preparation of 3-(but-3-enyl)-7-propyl-1,2,8,9-tetrafluorobibenzo[b,d]furan of the following structure

[0044]

[0045] 1. Suzuki coupling reaction

[0046] Under nitrogen protection at a flow rate of 0.6 mL / min, 7.10 g (21 mmol) of 4-bromo-3,5-difluoro-2-nitrophenylpropionaldehyde ethylene glycol acetal, 4.32 g (20 mmol) of 2,3 -Difluoro-6-hydroxy-4-n-propylphenylboronic acid, 6.44g (20mmol) tetra-n-butylammonium bromide, 7.18g (52mmol) potassium carbonate, 30mL N,N-dimethylformamide, 10mL distilled water Add it into a three-necked flask, raise the temperature to 65°C, and after the solid is completely dissolved, add 0.73g (0.63mmol) tetrakis(triphenyl)phosphine palladium, react at 65°C for 2 hours, add 130mL of distilled water, extract with ethyl acetate, organic Phase was washed with distilled water to neutrality, using silica gel as stationary phase and ethyl acetate as eluent column chromatography to obtain 5.91g of intermediate A-1 with the following structur...

Embodiment 2

[0063] Preparation of 3-butyl-7-propyl-1,2,8,9-tetrafluorobibenzo[b,d]furan with the following structural formula

[0064]

[0065] In Example 1, the 4-bromo-3,5-difluoro-2-nitrophenylpropionaldehyde ethylene glycol acetal used equimolar 3-bromo-2,4-difluoro-6-n-butyl Nitrobenzene replacement, according to the method of Example 1, through Suzuki coupling reaction, reduction reaction, fluorination reaction, to obtain 3-butyl-1,2,8,9-tetrafluoro-7-propyl bibenzo[b , d] furan, the total yield was 42%.

[0066] The NMR data of the obtained 3-butyl-1,2,8,9-tetrafluoro-7-propylbibenzo[b,d]furan are as follows:

[0067] 13 C-NMR (CDCl 3 as solvent, internal standard is TMS, 75MHz, ppm): 153.8, 146.0, 143.6, 143.4, 142.3, 142.0, 124.1, 123.5, 113.7, 107.9, 107.2, 106.9, 33.4, 31.4, 28.9, 24.1, 22.3, 14.1, 13.7 .

[0068] 1 H-NMR (CDCl 3 As a solvent, the internal standard is TMS, 300MHz, ppm): 6.98 (2H, s), 2.6 (4H, t), 1.59-1.65 (4H, m), 1.31 (2H, t), 0.90 (6H, t).

Embodiment 3

[0070] Preparation of 3-(but-3-enyl)-7-(trans-4-n-propylcyclohexyl)-1,2,8,9-tetrafluorobibenzo[b,d]furan of the following structure

[0071]

[0072] In Example 1, 2,3-difluoro-6-hydroxyl-4-n-propylphenylboronic acid was used with equimolar 2,3-difluoro-6-hydroxyl-4-(trans-4-n-propyl Cyclohexyl)-phenylboronic acid replacement, other steps are the same as in Example 1 to obtain 3-(but-3-enyl)-7-(trans-4-n-propylcyclohexyl)-1,2,8,9- Tetrafluorobibenzo[b,d]furan, the total yield is 43%.

[0073] The NMR data of the obtained 3-(but-3-enyl)-7-(trans-4-n-propylcyclohexyl)-1,2,8,9-tetrafluorobibenzo[b,d]furan are as follows:

[0074] 13 C-NMR (CDCl 3 as solvent, internal standard is TMS, 75MHz, ppm): 153.8, 146.0, 143.6, 143.4, 143.2, 143.0, 138.3, 124.9, 124.5, 116.4, 113.8, 113.0, 107.9, 107.5, 34.4, 31.4, 28.6, 24.1, 13.7 .

[0075] 1 H-NMR (CDCl 3 as solvent, internal standard is TMS, 300MHz, ppm): 6.98(1H, s), 6.96(1H, s), 5.82(1H, m), 5.02-5.07(2H, m), 2.56-2.62(3H, m...

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Abstract

The invention discloses a laterally tetrafluoro-substituted dibenzoheterocyclic compound and a preparation method thereof; the compound has the structural formula described in the specification, wherein in the formula, X represents O or S, l is 0 or 1, x is 0 or 2, y is 0 or 2, z is 0 or 1, R represents C2-C10 alkyl, and R' represents C2-C10 alkyl or C2-C10 alkenyl. The compound is synthesized through Suzuki coupling, reduction, fluorination, Wittig and other reactions, the yield and purity of the product are high, and the compound has large dielectric anisotropy and has wide application prospects in VA and IPS display modes.

Description

technical field [0001] The invention belongs to the technical field of materials, and in particular relates to a lateral tetrafluoro-substituted bibenzoheterocyclic compound and a preparation method thereof. Background technique [0002] VA and IPS display modes have the advantages of wide viewing angle and high contrast, and are widely used in large-screen TVs. Liquid crystal materials with negative dielectric anisotropy can be used in VA and IPS display modes. The resistivity of liquid crystal compounds containing cyano groups in the lateral direction is low, and it is difficult to meet the requirements of VA and IPS display modes. The dielectric anisotropy of lateral difluorine-substituted liquid crystal compounds is also negative, the resistivity is high, and the thermal performance is better than that of liquid crystal compounds containing cyano groups. It can be applied to VA and IPS display modes. Most of these compounds include 2, 3-difluoro-1,4-disubstituted benze...

Claims

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Application Information

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IPC IPC(8): C07D307/91C07D333/76C09K19/34
CPCC07D307/91C07D333/76C09K19/3405C09K19/3491C09K2019/3408
Inventor 姜祎徐虹宋小妹邓翀张化为
Owner SHAANXI UNIV OF CHINESE MEDICINE
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