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A class of substituted 4-phenylethynyl-1,8-naphthalimide compounds, its preparation method and application

A technology based on naphthalimide and phenylethynyl, applied in naphthalene dicarboxamide dyes/phthalimide dyes, chemical instruments and methods, organic chemistry, etc., can solve the problems of lack of performance fluorescent dichroic dyes, etc. Achieve the effect of shortening the display response time, reducing power consumption, and increasing the birefringence value

Inactive Publication Date: 2020-09-29
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

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

Method used

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  • A class of substituted 4-phenylethynyl-1,8-naphthalimide compounds, its preparation method and application
  • A class of substituted 4-phenylethynyl-1,8-naphthalimide compounds, its preparation method and application
  • A class of substituted 4-phenylethynyl-1,8-naphthalimide compounds, its preparation method and application

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Embodiment 1

[0029] Synthesis of Fluorescent Dichroic Dye C3

[0030] (1) Synthesis of intermediate (1)

[0031]

[0032] Add 2771mg (10mmol) of 4-bromo-1,8-naphthalene anhydride and 30mL of absolute ethanol to a 100mL single-necked bottle, add 1.48mL (12mmol) of n-butylamine under stirring at room temperature, heat up and reflux for reaction, and TLC detects that the reaction is complete. The mixture was cooled to room temperature and allowed to stand still to precipitate a light brown solid, which was filtered, washed and dried to obtain 2412 mg of a light white solid with a yield of 73%.

[0033] (2) Synthesis of intermediate (2)

[0034]

[0035] Add 332mg (1mmol) 4-bromo-N-n-alkyl-1,8-naphthalimide to a 50mL round bottom two-necked flask, then add 12mL triethylamine, add 8mg cuprous iodide, 15mg triphenyl Base phosphine and 7 mg ditriphenylphosphine palladium dichloride were used as catalysts. At this time, 100 μL (1 mmol) 2-methyl-3-butyn-2-ol was added with a syringe, under ...

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Abstract

The invention discloses a substituted 4-phenylethynyl-1,8-naphthalimide compound and a preparation method and application thereof. The substituted 4-phenylethynyl-1,8-naphthalimide compound has a structure C as shown in the specification. The substituted 4-phenylethynyl-1,8-naphthalimide compound and the preparation method thereof have the advantages that 1,8-anhydride naphthalene is used as the parent to design and prepare the novel-structured compound, the compatibility of the compound with main body liquid crystals is increased, and the liquid crystal compound has a high double refraction value; the compound is novel in structure, and the method is easy in raw material obtaining and green and environmentally friendly; the maximum absorption wavelength of the dye is 380 nanometers, the maximum emission wavelength of the dye is 458 nanometers, the dye emits blue-fluorescence, the fluorescence quantum yield of the dye reaches up to 0.75, the dye shows good bidirectional color ratio andorder parameters in liquid crystal E7, the maximum absorption order parameter of the dye is 0.65, and the maximum fluorescence order parameter of the dye is 0.45; the compound has a practical value in guest-host type liquid crystal displays.

Description

technical field [0001] The invention relates to a class of substituted 4-phenylethynyl-1,8-naphthalimide compounds. The preparation method and application thereof belong to the field of organic chemical industry. Background technique [0002] Obtaining information through vision is the main way for human beings to obtain information. More than 70% of information is through vision, so information display technology plays a very important role. Among the many display modes, the "guest-host" liquid crystal display (GH-LCD) is the display mode with the highest light source utilization, because it only needs one or even no polarizer when it works, which is compared to other polarizers that must use two 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. [0003] In the display...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D221/14C09K11/06C09B57/08C09K19/60
CPCC07D221/14C09B57/08C09K11/06C09K19/60C09K2211/1007C09K2211/1029
Inventor 李晓莲薄灵丹
Owner DALIAN UNIV OF TECH
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