A class of fluorescent dichroic dyes containing 4-(p-hydroxypiperidinyl)-1,8-naphthalene dinitrile, its preparation method and application

A dichroic dye and fluorescence technology, which is applied in the field of display materials, can solve the problems of dichroic dyes with many structures and varieties, and limited application performance, and achieve the effects of novel structure, easy-to-obtain raw materials, and improved solubility

Inactive Publication Date: 2016-06-01
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are many structures and varieties of dichroic dyes studied, but there are not many with good application performance and practical significance.

Method used

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  • A class of fluorescent dichroic dyes containing 4-(p-hydroxypiperidinyl)-1,8-naphthalene dinitrile, its preparation method and application
  • A class of fluorescent dichroic dyes containing 4-(p-hydroxypiperidinyl)-1,8-naphthalene dinitrile, its preparation method and application
  • A class of fluorescent dichroic dyes containing 4-(p-hydroxypiperidinyl)-1,8-naphthalene dinitrile, its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Synthesis of Fluorescent Dichroic Dye M1

[0030] (1) Synthesis of 4-bromoacenaphthylquinone (compound 1)

[0031]

[0032] Add 10.02g (55mmol) of acenaphthoquinone into a 250mL three-neck flask, then measure 12mL of liquid bromine with a syringe and add it into it. Saturated NaOH solution absorbs the tail gas, slowly heats to 65°C, and reacts for two hours under stirring. The reaction was stopped, the mixture was cooled to room temperature, and an appropriate amount of saturated Na 2 SO 3 The solution was freed of excess bromine and hydrogen bromide until the liquid was colorless. Suction filtration and washing until the filtrate is neutral. The crude product was recrystallized with glacial acetic acid after drying to obtain 12.34 g of a yellow solid with a yield of 86%. Melting point: 236.0-236.8°C.

[0033] (2) Synthesis of 3-bromo-8-thia-7,9-diaza-cyclopenta[a]acenaphthene 8,8-dioxide (compound 2)

[0034]

[0035] Add 11.49g (45mmol) of 4-bromoacenaphth...

Embodiment 2

[0051] Synthesis of Fluorescent Dichroic Dye M2

[0052] Except in step (5) with p-butoxybenzoic acid instead of p-methoxybenzoic acid reaction to obtain p-butoxybenzoyl chloride, in step (6) react with p-butoxybenzoyl chloride and compound 4 to obtain M2 Except, other operating steps are the same as in Example 1, and the yield of the target product M2 is 80%, melting point: 195.7-196.2°C.

[0053] 1 H-NMR (400MHz, CDCl 3 ):δ=8.48(dd, J=8.4,0.8Hz,1H),8.10(dd,J=7.2,0.8Hz,1H),8.02(dd,J=8.4,5.2Hz,3H),7.64(dd, J=8.4,7.2Hz,1H),7.21(d,J=8.0Hz,1H),6.93(d,J=8.8Hz,2H),5.30(s,1H),4.03(t,J=6.4Hz, 2H),3.41(s,2H),3.17(s,2H),2.29(s,2H),2.15(s,2H),1.85-1.74(m,2H),1.49(m,2H),0.99(t ,J=7.6Hz,3H).

[0054] ESIQ1MS: Calculated value: [C 28 h 27 N 3 o 3 ] + (m / z)=453.2052, measured value: [C 28 h 27 N 3 o 3 ] + (m / z) = 453.2048.

Embodiment 3

[0056] Synthesis of Fluorescent Dichroic Dye M3

[0057] Except in step (5) with p-hexyloxybenzoic acid instead of p-methoxybenzoic acid reaction to obtain p-hexyloxybenzoyl chloride, in step (6) react with p-hexyloxybenzoyl chloride and compound 4 to obtain M3 Except, other operating steps are the same as in Example 1, the yield of the target product M3 is 77%, and the melting point is 198.6-200.3°C.

[0058] 1 H-NMR (400MHz, CDCl 3 ):δ=8.48(d, J=8.4Hz, 1H), 8.10(d, J=7.2Hz, 1H), 8.02(dd, J=8.4, 5.3Hz, 3H), 7.68-7.60(m, 1H) ,7.21(d,J=8.0Hz,1H),6.93(d,J=8.8Hz,2H),5.30(s,1H),4.02(t,J=6.8Hz,2H),3.41(s,2H) ,3.17(s,2H),2.29(s,2H),2.16(s,2H),1.86-1.76(m,2H),1.47(dt,J=14.4,7.2Hz,2H),1.35(td,J =6.8,3.2Hz,4H),0.91(t,J=6.8Hz,3H). 13 C-NMR (126MHz, CDCl 3 ):δ=165.60,163.15,155.69,138.54,137.65,131.61,130.45,130.26,128.62,125.66,122.34,117.48,117.01,115.39,114.15,109.03,101.93,68.88,68.29,50.59,31.56,31.14,29.72, 29.07, 25.67, 22.61, 14.08.

[0059] TOFMSEI+: Calculated value: [C...

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Abstract

The invention discloses fluorescent dichroic dyes containing 4-(p-hydroxy-piperidyl)-1,8-naphthalene dicarbonitrile, which has a structure shown as a general formula M, wherein R is one of methyl, ethyl, n-propyl, n-butyl, n-amyl, n-hexyl, n-heptyl and n-octyl. By taking 1,8-naphthalene dicarbonitrile as a parent, a push-pull electronic system is formed by using the strong electron donating effect of N atoms and the strong electron withdrawing ability of double cyano-groups, then a p-(alkoxyl)benzoic acid is connected by virtue of esterification reaction, and thus a series of fluorescent dichroic dyes containing 1,8-naphthalene dicarbonitrile containing are designed and synthesized; therefore, the dyes are novel in structure, are prepared from easily available raw materials, and the synthesis method is simple; and the dyes have the maximum emission wavelength being 475nm, shows blue-fluorescence and have a good dichroic ratio and order parameters in liquid crystals E7; therefore, the dyes have a practical value in a guest-host liquid crystal display.

Description

technical field [0001] The invention relates to a class of fluorescent dichroic dyes containing 4-(p-hydroxypiperidinyl)-1,8-naphthalene dinitrile and an application thereof, belonging to the field of display materials. Background technique [0002] Along with the process of global informatization and digitization, the electronic information industry is ushering in a wave of tabletization, and a revolution in the field of display is taking place. The popular cathode ray tube display is gradually being replaced by the flat panel display represented by the thin film transistor liquid crystal display device, and the flat panel display technology and products have already occupied a dominant position in the display field. An ideal display should have the following characteristics: low operating voltage, low power consumption, small size, light weight, high contrast, fast response, wide viewing angle, etc. "Guest-host" liquid crystal display is one of the new fields of modern sc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B69/00G02F1/13
Inventor 李晓莲刘亚史凤丽赵赫
Owner DALIAN UNIV OF TECH
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