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

A naphthalimide and phenylethynyl technology, applied in naphthalene dicarboxamide dyes/phthalimide dyes, chemical instruments and methods, organic chemistry, etc., can solve problems such as lack of performance fluorescent dichroic dyes, etc. To achieve the effect of shortening the display response time, increasing the solubility, and reducing the response threshold voltage

Active Publication Date: 2021-12-07
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 Fluorescent dichroic liquid crystal dyes suitable for liquid crystal display products

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Synthesis of Fluorescent Dichroic Dye C1

[0031] (1) Synthesis of intermediate (1)

[0032]

[0033] Add 2771mg (10mmol) 4-bromo-1,8-naphthalene anhydride, 30mL absolute ethanol in 100mL single-necked bottle, add 1.48mL (12mmol) n-butylamine under stirring at room temperature, heat up and reflux reaction, TLC detection reaction is complete, will 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%.

[0034] (2) Synthesis of intermediate (2)

[0035]

[0036] Add 332mg (1mmol) 4‐bromo‐N‐n‐alkyl‐1,8‐naphthalimide to a 50mL round bottom two-necked bottle, then add 12mL triethylamine, add 8mg cuprous iodide, 15mg triphenyl Base phosphine and 7 mg ditriphenylphosphine palladium dichloride as catalysts, at this time, add 100 μL (1 mmol) 2-methyl-3-butyn-2-ol with a syringe, nitrogen protection, 80 ° C, and react for 2 ...

Embodiment 2

[0041] Synthesis and Characterization of Fluorescent Dichroic Dye C2

[0042]

[0043] Add 299mg (1mmol) butyldioxane bromobenzene and 277mg (1mmol) 4-alkyne-1,8-naphthalene anhydride to a 50mL round bottom two-necked bottle, add 20mL triethylamine, 8mg cuprous iodide, 5 mg of triphenylphosphine and 7 mg of ditriphenylphosphine palladium dichloride were used as catalysts, and were refluxed for 2 hours. The crude product was passed through a silica gel chromatography column, and the eluent was ethyl acetate:petroleum ether=1:3 (V / V), to obtain 56.89 mg of a light yellow powder with a yield of 11%. Melting point: 192.5°C, clearing point: 278.3°C. +ESI MS(M+H): C 41 h 50 N 2 o 4 , calculated value: 495.2410, measured value: 496.2451.

[0044] 1 H NMR (400MHz, CDCl 3 )δ8.73(dd, J=8.4,1.1Hz,1H),8.64(dd,J=7.3,1.1Hz,1H),8.56(d,J=7.6Hz,1H),7.95(d,J=7.6 Hz,1H),7.84(dd,J=8.3,7.3Hz,1H), 7.71–7.66(m,2H),7.56(d,J=8.1Hz,2H),5.46(s,1H),4.27(dd ,J=11.7,4.6Hz, 2H),4.22–4.15(m,2H),...

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Abstract

The invention discloses a class of compounds containing N-n-alkyl-4-phenylethynyl-1,8-naphthalimide, a preparation method and application thereof, and has a C structure. The invention uses 1,8-naphthalene anhydride as a matrix, designs and prepares a new structure compound, increases the compatibility between the compound and the host liquid crystal, and the liquid crystal compound has a high birefringence value. The structure is novel, the raw materials are easy to obtain, and the synthesis method is green and environmentally friendly; the maximum absorption wavelength of the dye is 376nm, and the maximum emission wavelength is 436nm, showing blue fluorescence, and the fluorescence quantum yield can reach up to 0.64, which is better in liquid crystal E7. Dichroic ratio and order parameter, the absorption order parameter is 0.56, and the fluorescence order parameter is 0.33. It has practical value in guest-host type liquid crystal display.

Description

technical field [0001] The invention relates to a class of compounds containing N-n-alkyl-4-phenylethynyl-1,8-naphthalimide and its preparation method and application, belonging 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, "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 env...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/10C09B57/08C09K11/06C09K19/34G02F1/137
CPCC07D405/10C09B57/08C09K11/06C09K19/3447C09K2211/1007C09K2211/1029C09K2211/1088G02F1/13725
Inventor 李晓莲薄灵丹
Owner DALIAN UNIV OF TECH
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