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A class of compounds containing 4-(p-biphenylethynyl)-1,8-naphthalene anhydride, its preparation method and application

A technology of alkyl biphenyl acetylene and compound, applied in the field of display materials, can solve the problem of lack of performance fluorescent dichroic dyes and the like

Inactive Publication Date: 2021-06-22
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to solve the problem of lack of fluorescent dichroic dyes with good performance in the prior art, the present invention provides a kind of yellow-green fluorescence, high fluorescence quantum yield, and better dichroic performance in liquid crystal E7 Ratio and order parameters, liquid crystal with a wide temperature range, high birefringence value, easy to dissolve in the main liquid crystal E7, can reduce the response time of liquid crystal E7, a fluorescent dichroic liquid crystal dye suitable for liquid crystal display products

Method used

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  • A class of compounds containing 4-(p-biphenylethynyl)-1,8-naphthalene anhydride, its preparation method and application
  • A class of compounds containing 4-(p-biphenylethynyl)-1,8-naphthalene anhydride, its preparation method and application
  • A class of compounds containing 4-(p-biphenylethynyl)-1,8-naphthalene anhydride, its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Synthesis of Fluorescent Dichroic Dye A1

[0032] (1) Synthesis of intermediate 2‐methyl‐2‐hydroxy‐3‐butynyl p-propylbiphenyl (compound 2)

[0033]

[0034] Add 233mg (1mmol) of 4'-bromo-4-n-propylbiphenyl to a 50mL round-bottomed two-necked bottle, then add 20mL of triethylamine as acid-binding agent and solvent, and use a nitrogen-filled balloon for anaerobic protection , then add a catalytic amount of ditriphenylphosphine palladium dichloride, triphenylphosphine, CuI as a catalyst in the system. At this time, add 100μL (1.1mmol) 2‐methyl‐3‐butyn‐2‐alcohol, and reflux the reaction. The crude product was passed through a silica gel chromatography column, and the eluent was a mixed solution of petroleum ether and dichloromethane, and the solvent was removed under reduced pressure to obtain 160.9 mg of a white solid, with a yield of 61%.

[0035] (2) Synthesis of intermediate p-propylbiphenylacetylene (compound 3)

[0036]

[0037] Add 278mg (1mmol) of 2-methyl-...

Embodiment 2

[0046] Fluorescent dichroic dye A2 Synthesis and characterization of

[0047] The difference from Example 1 is that in step (4), n-propanolamine is used to replace ethanolamine, the eluent is a mixture of dichloromethane and ethyl acetate, and the yield is 80%. Melting point: 127.95°C, clearing point: 251.7°C.

[0048] +ESI MS(M+H): C 32 h 27 NO 3 , calculated value: 474.2024, measured value: 474.2048.

[0049] 1 H NMR (400MHz, CDCl 3 )δ8.79(dd, J=8.4,1.1Hz,1H),8.67(dd,J=7.3,1.1Hz,1H),8.58(d,J=7.6Hz,1H),7.98(d,J=7.6 Hz,1H),7.87(dd,J=8.3,7.3Hz,1H), 7.76–7.71(m,2H),7.69–7.65(m,2H),7.56(d,J=8.2Hz,2H),7.29 (d, J=8.2Hz, 2H), 4.36(dd, J=12.8, 6.6Hz, 2H), 3.61(d, J=5.3Hz, 2H), 3.13(s, 1H), 2.71–2.60 (m, 2H), 2.07–1.95(m, 2H), 1.70(dq, J=14.8, 7.4Hz, 2H), 0.99(t, J=7.3Hz, 3H). 13 C NMR (126MHz, CDCl 3 )δ164.55,164.27,142.73,142.16,137.22,132.65,132.32, 131.85,131.46,130.65,129.07,128.03,127.42,126.92,122.49,121.46,120.51, 99.63,86.74,58.95,37.69,36.87,31.01,24.49,13.85 . ...

Embodiment 3

[0051] Fluorescent dichroic dye A3 Synthesis and characterization of

[0052] Add 459mg (1mmol) of A1 obtained in Example 1 in a 50mL two-necked bottle, then add an appropriate amount of dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine DMAP as a catalyst in the reaction system, and stir evenly Slightly excess acetic acid was added, and the reaction was completed at room temperature. Dichloromethane and petroleum ether were used as developing solvents, and silica gel column chromatography was used for separation and purification. The yield: 66%. Melting point: 114.8°C, clearing point: 142.8°C.

[0053] +ESI MS (M+Na): C 33 h 27 NO 4 , calculated value: 524.1838, measured value: 524.1830.

[0054] 1 H NMR (400MHz, CDCl 3 )δ8.80(d, J=8.4Hz, 1H), 8.69(dd, J=7.3, 1.0Hz, 1H), 8.61(t, J=6.3Hz, 1H), 8.00(d, J=7.6Hz, 1H),7.91–7.85(m,1H),7.79–7.73(m, 2H),7.72–7.67(m,2H),7.59(d,J=8.2Hz,2H),7.32(d,J=8.2Hz ,2H),4.53(t,J=5.3Hz,2H),4.47(t,J=5.2Hz,2H),2.71–2.62(m,2H),2.05(...

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Abstract

A class of compounds containing 4-(p-biphenylethynyl)-1,8-naphthalene anhydride and its preparation method and application, having a structure of general formula A, wherein R1 is selected from ethyl, n-propyl, n-butyl, n-pentyl One of base, n-hexyl, n-heptyl and n-octyl, n is selected from one of 2, 3 and 4, R2 is selected from methyl, ethyl, n-propyl, n-butyl, n-pentyl, One of the n-hexyl groups. A series of 1,8-naphthalene anhydride fluorescent dichroic liquid crystal dyes were designed and synthesized, with novel structure, easy-to-obtain raw materials, and simple synthesis method; the compound of the invention has high fluorescence intensity and is also conducive to the formation of liquid crystal phases. The dye has a maximum absorption wavelength of 393nm and a maximum emission wavelength of 500nm, showing blue fluorescence with a fluorescence quantum yield of up to 0.78. It shows a better dichroic ratio and order parameters in liquid crystal E7, and the maximum absorption is The order parameter is 0.75, and the maximum fluorescence order parameter is 0.64. It has high birefringence and is used in guest-host liquid crystal displays.

Description

technical field [0001] The invention relates to a class of compounds containing 4-(p-alkylbiphenylethynyl)-1,8-naphthalene anhydride, a preparation method and application thereof, and belongs to the field of display materials. Background technique [0002] There are many ways to obtain human information, but more than 70% of the information is obtained through visual channels, so information display technology plays a very important role. Among the many display modes, "guest-host" liquid crystal display (GH-LCD) is the display mode with the highest utilization rate of light source, because it only needs one polarizer or even no polarizer when working, which is compared with other polarizers that must use two polarizers. In terms of the display mode of the polarizer, it greatly improves the utilization rate of the light source. In addition, GH-LCD also has the characteristics of wide viewing angle, bright colors, high brightness, and can be applied to special environments. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D221/14C09K11/06C09B57/08C09K19/34G02F1/137
CPCC07D221/14C09B57/08C09K11/06C09K19/3447C09K2211/1007C09K2211/1029G02F1/13725
Inventor 李晓莲薄灵丹
Owner DALIAN UNIV OF TECH
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