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Fluorine-containing trans-decalin esters compounds and synthesis method thereof

A technology of decahydronaphthyl esters and compounds, which is applied in the field of trans-decalin compounds and their synthesis, can solve the problems of narrow liquid crystal phase intervals and cannot meet the requirements, and achieve wide liquid crystal phase intervals, easy separation, and simple operation Effect

Inactive Publication Date: 2008-03-19
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The monocyclic skeletons (such as cyclohexanes, benzene rings, and pyrimidines) in the molecules of existing display liquid crystal materials each have different advantages in photoelectric properties, but the common disadvantage is that the liquid crystal phase interval is relatively narrow, which cannot meet the needs of high-end TFTs. (thin film transistor) liquid crystal display requirements, so seeking new liquid crystal molecular structure has become the common focus of chemical workers

Method used

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  • Fluorine-containing trans-decalin esters compounds and synthesis method thereof
  • Fluorine-containing trans-decalin esters compounds and synthesis method thereof
  • Fluorine-containing trans-decalin esters compounds and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Example 1: Preparation of 4-(4'-fluorobenzoyloxy)benzoic acid (6-n-pentyl) trans-decalin-2-ester

[0017] English name: 4-((6’-pentyl-decahydronaphthalen-2-yloxy)carbonyl)phenyl4-fluorobenzoate

[0018] Structural formula:

[0019]

[0020] Subnumerary: 466.58

[0021] Appearance: white solid

[0022] Melting point: 113.69°C

[0023] Clearing point: 213.07℃

[0024] Infrared spectrum (using Perkin-Elmer983G infrared spectrometer, KBr tablet)

[0025] υ max (cm -1 ): 2918, 2850, 1730, 1709, 1604, 1510, 1463, 1266, 1205, 1163, 1116, 1064, 1012, 885, 846, 762

[0026] NMR spectrum 1 H spectrum (500 MHz, deuterated chloroform) δ / ppm: 8.22 (m, 2H, ArH), 8.10 (m, 2H, Ar H ), 7.28 (m, 2H, Ar H ), 7.19 (m, 2H, Ar H ), 4.97 (m, 1H, OC H ), 0.63-2.16(m, 27H)

[0027] NMR spectrum 13 C spectrum (126 MHz, deuterated chloroform) δ / ppm: 167.45, 165.41, 163.39, 154.39, 133.07, 133.00, 131.33, 128.83, 125.53, 125.51, 121.72, 116.14, 115.97, 74.28, 42.19, 40.9. , 37.49...

example 2

[0029] Example two: with dry dichloromethane as solvent, add 6-n-pentyl-2-hydroxyl-trans decahydronaphthalene (3.5g, 15.6mmol), 4-(4-fluoro Benzoyloxy)benzoic acid (4.5g, 1.72mmol) DCC (3.5g, 17.2mmol) and DMAP (2.1g, 17.2mmol), after stirring at room temperature for 10 hours, stop the reaction, filter, and remove the solvent under reduced pressure Column chromatography (petroleum ether: ethyl acetate = 12:1). The resulting product was recrystallized with ethanol to obtain 5.4 grams of a white solid to obtain the compound 4-(4'-fluorobenzoyloxy)benzoic acid (6-n-pentyl)trans-decalin-2-ester with a yield of 74% .

Embodiment 3

[0030] Example 3: Preparation of 4-(4-n-heptyloxy-benzoyloxy)benzoic acid (6-n-pentyl)trans-decalin-2-ester. The structural formula is:

[0031]

[0032] Molecule: 534.73, appearance: white solid, melting point: 82.9°C, clearing point: 199.5°C

[0033] Spectral data:

[0034] Infrared spectrum (using Perkin-Elmer983G infrared spectrometer, KBr tablet)

[0035] υ max (cm -1 ): 2918, 2850, 1730, 1709, 1604, 1510, 1463, 1266, 1205, 1163, 1116, 1064, 1012, 885, 846, 762

[0036] NMR spectrum 1 H spectrum (500 MHz, deuterated chloroform) δ / ppm: 8.13 (d, 2H, ArH), 8.10 (d, 2H, Ar H ), 7.27 (d, 2H, Ar H ), 6.97(d, 2H, Ar H ), 4.96 (m, 1H, OC H ), 4.04(t, 2H, OC H 2 ), 0.63-2.16(m, 39H)

[0037] NMR spectrum 13C spectrum (126 MHz, deuterated chloroform) δ / ppm: 165.53, 164.58, 163.89, 154.77, 132.52, 131.24, 128.51, 121.85, 121.24, 114.52, 74.21, 68.51, 42.13, 41.22, 450.09, 37.81, 37.11, 3 , 33.68, 33.09, 32.35, 32.09, 31.91, 31.86, 29.24, 29.18, 26.76, 26.09, 22.86, ...

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Abstract

The invention relates to a fluorine-containing trans-decalin ester compound and a synthesis method. The structural formula of the compound is shown in the figure on the right, and wherein, Ar is the alkyl of 2-FC6H4, 3-FC6H4, 4-FC6H4, 2, 4-F2C6H3 or 4-CF3C6H4, R2is alkyl between C1 and C5. In the preparation method for the compound, according to the stoichiometric ratio of 1:1.0 to 1.5:1.0 to 1.5:1.0 to 2.0, 6-alkyl-2-hydroxyl-trans-decalin, 4-(fluorine-containing benzoyloxy) benzoic acid, DCC and DMAP are resolved in dry dichloromethane, stired for ten to twenty hours, and after column chromatography separation, recrystallized by anhydrous alcohol in order to generate the fluorine-containing trans-decalin ester compound. The utility model is favorable to industrialized production and has the advantages of easy acquisition of materials, simple operation, high yield rate and convenient separation. The invention introduces the trans-decalin structure into the compound, so the generated compound has a wide liquid crystal phase interval.

Description

technical field [0001] The invention relates to a trans-decalin compound and a synthesis method thereof, in particular to a fluorine-containing trans-decalin compound and a synthesis method thereof. Background technique [0002] In the past two decades, the rapid development of liquid crystal technology and liquid crystal display industry has brought unprecedented vitality to this field. Due to its unique photoelectric properties, liquid crystal materials are widely used in industry and people's daily life. In recent years, with the breakthrough of thin-film transistor TFT liquid crystal display technology, the application of flat liquid crystal display has become more and more extensive, and it has replaced cathode picture tube CRT display to become the mainstream of today's flat panel display. Among them, the small molecule liquid crystal materials used in liquid crystal displays are usually some rod-shaped liquid crystal small molecule compounds with a nematic phase. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/773C07C67/08
Inventor 万文杨城蒋海珍郝健
Owner SHANGHAI UNIV
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