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A kind of alkyne liquid crystal compound containing pyridine terminal group and its preparation method and application

A liquid crystal compound, pyridyl acetylenic alcohol technology, applied in chemical instruments and methods, liquid crystal materials, photosensitive equipment, etc., to achieve the effect of good compatibility and large positive dielectric anisotropy

Active Publication Date: 2018-08-24
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] However, there are no reports on the application of liquid crystal materials for display in solar cells.

Method used

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  • A kind of alkyne liquid crystal compound containing pyridine terminal group and its preparation method and application
  • A kind of alkyne liquid crystal compound containing pyridine terminal group and its preparation method and application
  • A kind of alkyne liquid crystal compound containing pyridine terminal group and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Under the protection of nitrogen, add 8.20g (40.00mmol) p-iodopyridine, 5.30g (60.00mmol) 2-methyl-3-butyn-2-ol, 0.46g (0.40mmol) tetrakis triphenyl Phosphine-based palladium, 0.38g (2.00mmol) cuprous iodide, 0.84g (3.20mmol) triphenylphosphine and 25g (250.00mmol) triethylamine, 200mL DMF, reflux and stir the reaction for 12 hours under nitrogen protection, and cool to room temperature, extracted with dichloromethane, the organic phase was washed 3 times with a saturated ammonium chloride solution, the organic phases were combined, washed with water until neutral, dried over anhydrous magnesium sulfate, and concentrated to obtain 5.16 g of a yellow-brown solid, namely pyridyl Alkynyl alcohol 1 (HPLC>92%), its productive rate is 80%, and concrete chemical reaction equation is as follows:

[0044]

[0045] Under nitrogen protection, 1.26g (7.8mmol) pyridyl alkynol 1, 0.25g (0.78mmol) tetra-n-butylammonium bromide, 5.24g (93.6mmol) potassium hydroxide, 16mL toluene and...

Embodiment 2

[0053] In Example 1, the 4-(trans-(4-n-propylcyclohexyl) ethyl) iodobenzene 3I used was used with equimolar 4-(trans-(4-n-pentylcyclohexyl) ethyl) iodine Benzene 5I was replaced, and other steps were the same as in Example 1 to obtain white crystals-containing pyridine terminal group alkyne liquid crystal molecules 5N, the yield was 43%, and the chemical name was 1-{4-[2-(4-n-pentyl Cyclohexyl) ethyl] phenyl}-2-[4-pyridyl] acetylene, the specific reaction equation is as follows:

[0054]

[0055] The structural characterization data of the obtained pyridine terminal group-containing alkyne liquid crystal compound are as follows:

[0056] 13 C-NMR (CDCl 3 is the solvent, the internal standard is TMS, 101MHz, ppm): 149.73, 144.88, 131.85, 131.69, 128.55, 125.48, 119.17, 94.40, 86.16, 39.02, 37.82, 37.51, 37.44, 33.41, 33.24, 33, 267, 32.26 , 14.14.

[0057] 1 H-NMR (CDCl 3 As a solvent, the internal standard is TMS, 400MHz, ppm): 8.59(d, J=5.4Hz, 2H), 7.47(d, J=8.3Hz, 2...

Embodiment 3

[0061] The use of the alkyne liquid crystal compound containing pyridine terminal groups prepared in Example 1 in the preparation of dye-sensitized solar cells, the specific use method is:

[0062] 1. Conductive glass pretreatment

[0063] Clean the conductive glass in detergent, ethanol, and deionized water with an ultrasonic wave at a frequency of 40 Hz and a power of 100 W for 30 minutes to 1 hour, and dry it at 110°C for later use.

[0064] 2. Preparation of dye solution

[0065] Dissolve the alkyne liquid crystal compound containing pyridine terminal groups in a mixed solvent with a volume ratio of acetonitrile and tert-butanol of 1:1 to prepare a dye solution with a concentration of 0.3 mmol / L.

[0066] 3. Preparation of electrolyte solution

[0067] Add tetrabutylammonium iodide, lithium iodide, iodine, and p-tert-butylpyridine into acetonitrile to prepare an electrolyte solution. The concentrations are 0.6mol / L, 0.1mol / L, 0.05mol / L, and 0.5mol / L, respectively.

[0...

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Abstract

The invention discloses a pyridine-containing terminal alkyne liquid crystal compound and a preparation method and application thereof. The structural formula of the compound is shown in the description, wherein in the formula, CnH2n+1 represents C2-C5 linear alkyl. The liquid crystal compound is obtained through a sonogashira coupling reaction of pyridyl alkynol and aryl iodide, the synthesis method is simple, the cost is low, and the liquid crystal compound is suitable for industrial production. The liquid crystal compound has positive dielectric anisotropy and a certain nematic phase liquid crystal interval, has a high clearing point, has excellent intermiscibility with other liquid crystal compounds, can be applied to dye-sensitized solar cells as a dye sensitizer molecule and can also be applied to an IPS display mode or a TN display mode.

Description

technical field [0001] The invention belongs to the technical field of liquid crystal compounds, and in particular relates to an alkyne liquid crystal compound containing a pyridine terminal group, and a preparation method and application of the liquid crystal compound. Background technique [0002] Since the development of liquid crystal materials, they have been applied in many fields such as liquid crystal displays, liquid crystal optical devices, high-strength elastic materials, and organic solar cell materials. Therefore, liquid crystal materials, as an interdisciplinary research hotspot, have been extensively studied by researchers. Against the backdrop of the energy crisis and environmental pollution posing increasing challenges to global sustainable development, solar cells are increasingly being valued by the scientific and industrial circles. In the past two years, liquid crystal researchers have done a lot of experimental research, hoping to apply liquid crystal ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K19/34C09B57/00H01G9/20
CPCY02E10/542
Inventor 安忠维陈然马雯燕陈新兵陈沛
Owner SHAANXI NORMAL UNIV
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