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Small-angle reverse v-shaped ferroelectric liquid crystal compound and synthetic method thereof

A liquid crystal compound, ferroelectric technology, applied in chemical instruments and methods, liquid crystal materials, organic chemistry, etc., to achieve the effects of low cost of raw materials, broad application prospects, and simple synthesis methods

Inactive Publication Date: 2012-12-12
BEIHANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this conclusion is only based on the induction and summary of historical data. The molecular model construction and ferroelectricity theory are both based on the central ring structure of 120°. There is little research on banana-shaped ferroelectric liquid crystals with small-angle central rings (less than 105°). someone involved

Method used

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  • Small-angle reverse v-shaped ferroelectric liquid crystal compound and synthetic method thereof
  • Small-angle reverse v-shaped ferroelectric liquid crystal compound and synthetic method thereof
  • Small-angle reverse v-shaped ferroelectric liquid crystal compound and synthetic method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029]

[0030] 1) Synthesis of dialdehyde compound 11

[0031]In a 200ml three-necked flask, under nitrogen protection and magnetic stirring, 1,7-dihydroxynaphthalene 10 (1.50g, 9.36mmol), p-aldehyde benzoic acid 3 (2.163g, 20.58mmol), dicyclohexylcarboimide ( 4.83g, 23.4mmol), 4-dimethylaminopyridine (catalytic amount), dichloromethane solvent (80ml), react at 20°C to 50°C. TLC traced until the disappearance of the raw material, and the reaction time was 48 hours to 96 hours. The reaction solution was filtered, and most of the solvent in the filtrate was evaporated by a rotary evaporator, and chloroform was used as an eluent to pass through the column to obtain a white solid, which was then recrystallized with chloroform / methanol to obtain dialdehyde compound 11, as shown in the reaction formula (5) shown.

[0032]

[0033] 2) Synthesis of 4-aminophenyltetradecane 8

[0034] 200ml single-necked flask, magnetically stirred, sequentially added 4-nitrothiophenol 5 (2.0...

Embodiment 2

[0040]

[0041] 1) Synthesis of dialdehyde compound 14

[0042] In a 200ml three-necked flask, under nitrogen protection and magnetic stirring, 1,7-dihydroxyanthracene 13 (1.50g, 7.13mmol), p-aldehyde benzoic acid 3 (2.36g, 15.70mmol), dicyclohexylcarboimide ( 5.88g, 28.50mmol), 4-dimethylaminopyridine (catalytic amount), dichloromethane solvent (100ml), and react at 20°C to 50°C. TLC traced until the disappearance of the raw material, and the reaction time was 48 hours to 96 hours. The reaction solution was filtered, and most of the solvent was evaporated by a rotary evaporator, and chloroform was used as an eluent to pass through the column to obtain a white solid, which was then recrystallized with chloroform / methanol to obtain a white solid dialdehyde compound 14, as shown in the reaction formula (7) shown.

[0043]

[0044] 2) Synthesis of 4-aminophenyltetradecane 8

[0045] 200ml single-necked flask, magnetic stirring, sequentially add 4-nitrothiophenol 5 (3.00g...

Embodiment 3

[0051]

[0052] 1) Synthesis of dialdehyde compound 17

[0053] In a 200ml three-necked flask, nitrogen protection, magnetic stirring, successively add 1,7-dihydroxyl 16 (2.00g, 10.10mmol), p-aldehyde benzoic acid 3 (3.79g, 25.24mmol), dicyclohexylcarboimide ( 8.34g, 40.40mmol), 4-dimethylaminopyridine (catalytic amount), dichloromethane solvent (100ml), and react at 20°C to 50°C. TLC traced until the disappearance of the raw material, and the reaction time was 48 hours to 96 hours. The reaction solution was filtered, and most of the solvent was evaporated by a rotary evaporator, and chloroform was used as an eluent to pass through the column to obtain a white solid, which was then recrystallized with chloroform / methanol to obtain a white solid dialdehyde compound 17, as shown in the reaction formula (9) shown.

[0054]

[0055] 2) Synthesis of 4-aminophenyltetradecane 8

[0056] 200ml single-necked flask, magnetic stirring, sequentially add 4-nitrothiophenol 5 (2.50g...

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Abstract

The invention relates to a small-angle reverse v-shaped ferroelectric liquid crystal compound and a synthetic method thereof. The compound has a molecular formula shown in the specification, wherein a 60-degree small-angle center ring R is adopted in a molecular structure, and R is 1, 7-disubstituted naphthaline, or 1, 8-disubstituted anthracene, or 1, 8-disubstituted phenalene or 1, 8-disubstituted phenanthrene; a side chain is a Schiff base type side chain, and a linking group of the side chain and the center ring is an ester base (-COO); and an end base is an alkyl sulfide base (-SC14H29).The compound not only has simple synthetic method and low raw material cost, but also has excellent ferroelectric property, characteristic single-peak reverse current is expressed in a vertical triangular wave electric field test, the spontaneous polarization value of electric field saturation can reach 360nC / cm<2>, and the spontaneous polarization response time under a square wave electric fieldis about 6ms. The compound has broad application prospects on the aspects of photoelectric switches, nonlinear optical second harmonics, fast-response liquid-crystal display and the like.

Description

technical field [0001] The invention relates to a small-angle ∧-shaped ferroelectric liquid crystal compound and a synthesis method thereof. Background technique [0002] The development of new displays, as the first item of China's major high-tech industrialization project, appeared in the "Government Work Report" in 2008 and 2009. As the core technology of new displays, the research on ferroelectric liquid crystal materials and liquid crystal display technology is extremely urgent. At present, the ferroelectric liquid crystal display on the market generally has the shortcomings of slow response speed and narrow viewing angle. The solution is mainly to improve the performance of the alignment film of the liquid crystal material in the display and increase the optical compensation effect from the technical aspect, and the ferroelectric liquid crystal material There is less research. [0003] The research on ferroelectric liquid crystal materials can be traced back to 1975....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C323/36C07C319/20C09K19/28
Inventor 詹茂盛李晓东王凯
Owner BEIHANG UNIV