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N-methyl substituted benzimidazole liquid crystal compound containing acetylenic bond and preparation method thereof

A liquid crystal compound, methyl-substituted technology, applied in chemical instruments and methods, liquid crystal materials, organic chemistry, etc., can solve the problems that resistivity is difficult to achieve active drive, reduce liquid crystal viscosity, strong electrostatic effect, etc., and achieve high optical Anisotropy, improved response speed, simple operation effect

Inactive Publication Date: 2019-11-22
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although cyano or isothiocyanate can significantly increase the Δn of liquid crystals, the larger dipole moment makes the intermolecular electrostatic interactions containing these groups very strong, which is not conducive to reducing the viscosity of liquid crystals; moreover, cyano and isothiocyanate Even after repeated purification of thiocyanate liquid crystals, its resistivity is still difficult to meet the requirements of active driving

Method used

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  • N-methyl substituted benzimidazole liquid crystal compound containing acetylenic bond and preparation method thereof
  • N-methyl substituted benzimidazole liquid crystal compound containing acetylenic bond and preparation method thereof
  • N-methyl substituted benzimidazole liquid crystal compound containing acetylenic bond and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] 1. Preparation of 4-(4-(1,3-dioxolan-2-yl)phenyl)-2-methylbut-3-yn-2-ol

[0047]Add p-bromobenzaldehyde 10g (49.6mmol), p-toluenesulfonic acid 2.20g (12.7mmol), ethylene glycol 70mL (1120.0mol) into a 250mL single-necked flask equipped with a condenser tube and a stirring bar, and add 100 mL of trichloromethane was used as a solvent, and after 6 hours of constant temperature reflux reaction at 60°C, it was washed with water, extracted with dichloromethane, and the solvent was distilled off under reduced pressure to obtain a white liquid. The resulting white liquid was added to a 250mL three-necked flask equipped with a stirring bar, and then 2.02g (24.0mmol) of 2-methyl-3-butyn-2-ol, 0.21g (1.1mmol) of cuprous iodide, and triphenyl Base phosphine 0.58g (2.2mmol), and add triethylamine 80mL as a solvent, under the protection of nitrogen, 80 ℃ reflux reaction for 1 hour, add tetrakis (triphenylphosphine) palladium 0.50g (0.4mmol), continue to react for 8 hours . After t...

Embodiment 2

[0064] In step 4 of this example, the o-phenylenediamine in step 4 of example 1 is replaced with equimolar 4-methylbenzene-1,2-diamine, and the other steps are the same as in example 1 to obtain 2- (4-((4-(pentyloxy)phenyl)ethynyl)phenyl)-1,6-dimethyl-1H-benzimidazole 0.61 g, yield 35.5%.

[0065]

[0066] The spectral data of the product are as follows:

[0067] IR(KBr)v(cm -1 ): 2927, 2862, 2356, 1598, 1502, 1458, 1386, 1242, 1026, 837, 588, 528.

[0068] 1 H NMR (CDCl 3 ,400MHz): 7.75-7.73(m, 2H), 7.70-7.68(m, 1H), 7.64-7.59(m, 2H), 7.48-7.46(m, 2H), 7.17-7.12(m, 2H), 6.88 -6.86(d, J=9.24, 2H), 3.97-3.95(t, 3 J H-H =7.83Hz, 2H), 3.88-3.81(s, 3H), 2.52-2.50(s, 3H), 1.86-1.74(m, 2H), 1.49-1.32(m, 4H), 0.94-0.92(t, 3 J H-H =7.70Hz, 3H).

[0069] MS m / z (%): theoretical 408.54, found 408.23.

[0070] The above structural identification data show that the synthesized compound is indeed 2-(4-((4-(pentyloxy)phenyl)ethynyl)phenyl)-1,6-dimethyl-1H-benzimidazole.

Embodiment 3

[0072] In step 4 of this example, the o-phenylenediamine in step 4 of example 1 is replaced with equimolar 4-nitrobenzene-1,2-diamine, and the other steps are the same as in example 1 to obtain 2- (4-((4-(pentyloxy)phenyl)ethynyl)phenyl)-1-methyl-6-nitro-1H-benzimidazole 0.43 g, yield 25%.

[0073]

[0074] The spectral data of the product are as follows:

[0075] IR(KBr)v(cm -1 ): 2933, 2862, 2206, 1596, 1512, 1342, 1247, 1174, 1016, 823, 738, 526.

[0076] 1 H NMR (CDCl 3 ,400MHz): 8.40-8.34(m, 1H), 8.26-8.23(m, 1H), 7.85-7.83(m, 1H), 7.81-7.73(m, 2H), 7.68-7.65(m, 2H), 7.48 -7.43(m, 2H), 6.88-6.86(d, J=8.61, 2H), 4.05-3.97(t, 3 J H-H =758Hz, 2H), 3.97-3.95(s, 3H), 1.81-1.77(m, 2H), 1.47-1.36(m, 4H), 0.94-0.92(t, 3 J H-H = 8.61Hz, 3H).

[0077] MS m / z (%): theoretical 439.51, found 440.5.

[0078] The above structural identification data show that the synthesized compound is indeed 2-(4-((4-(pentyloxy)phenyl)ethynyl)phenyl)-1-methyl-6-nitro-1H-benzo imidazole. ...

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Abstract

The invention discloses an acetylene bond-containing N-methyl substituted benzimidazole liquid crystal compound and a preparation method thereof, and belongs to the technical field of materials. The structural formula of the liquid crystal compound is shown in the specification, wherein R represents C5-C12 straight-chain alkyl, and X represents hydrogen, methyl or nitro group. The compound is prepared with p-bromobenzaldehyde, 2-methyl-3-butyne-2-ol, 1-iodine-4-(alkoxy)benzene, o-phenylenediamine compounds and methyl iodide as raw materials through reactions such as Sonogashira coupling, nucleophilic addition, ring closing and the like. The liquid crystal compound has large birefringence, and the preparation method is simple in step and can be used in a liquid crystal photoelectric deviceto improve the response speed of the liquid crystal photoelectric device.

Description

technical field [0001] The invention belongs to the technical field of liquid crystal materials, and in particular relates to an N-methyl substituted benzimidazole liquid crystal compound containing an alkyne bond and a preparation method thereof. Background technique [0002] Liquid crystal materials with great development prospects are now used in display devices such as smartphones, car navigation dashboards, tablets, portable notebook computers, and high-definition large-screen TVs, as well as non-display fields such as light modulators, laser beam deflection, and adaptive optics. . Liquid crystal materials can adjust and optimize more than a dozen parameters in optoelectronic devices, including driving voltage, number of driving channels, viscoelasticity, viewing angle, energy consumption, etc., which can make the display more prominent. [0003] Among its many applications, improving the response speed of liquid crystal displays has always been a difficult problem in ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/18C09K19/34
CPCC07D235/18C09K19/348
Inventor 陈新兵刘国庆党佳珍安忠维陈沛
Owner SHAANXI NORMAL UNIV