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A fluorophenylindole compound, its application as a red organic light-emitting material and its preparation method

A technology of substituted phenylindole and luminescent materials, applied in luminescent materials, chemical instruments and methods, organic chemistry, etc., can solve problems limited to the field of medicine, few researches on up-conversion luminescent materials, less preparation and research of luminescent materials, etc. problems, to achieve the effects of reducing interactions, enhancing upconversion luminescence performance, and enhancing chemical stability

Active Publication Date: 2017-05-24
INSTITUTE OF ANALYSIS GUANGDONG ACADEMY OF SCIENCES (CHINA NATIONAL ANALYTICAL CENTER GUANGZHOU)
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] Cycloalkanone curcumin analogs are a class of compounds with various physiological activities such as anti-tumor, anti-oxidation, and anti-bacterial. In recent years, these compounds have received great attention from researchers and extensive research has been carried out. However, these Research work is often limited to the field of medicine, and there are very few studies as upconversion luminescent materials
[0009] 3-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)acrolein is an important intermediate for the synthesis of fluvastatin, a drug for the prevention and treatment of cardiovascular diseases, prior art Most of the research on it is limited to the synthesis method, process research, and application as a pharmaceutical intermediate, while the preparation and research on luminescent materials are rarely
[0010] At present, using 3-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)acrolein as raw material, two fluorophenylindole The indole functional group is connected to form a bisfluorophenylindole allyl cyclohexanone compound, and the research on its up-conversion luminescence characteristics has not been reported in the prior art.

Method used

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  • A fluorophenylindole compound, its application as a red organic light-emitting material and its preparation method
  • A fluorophenylindole compound, its application as a red organic light-emitting material and its preparation method
  • A fluorophenylindole compound, its application as a red organic light-emitting material and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Example 1: 3,5-bis(3-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)allylidene)cyclohexanone (I) preparation:

[0042] In a 250 ml round bottom flask, dissolve cyclohexanone (1 mmol) and 3-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)acrolein (2 mmol) In 50 ml of ethanol or methanol, 10 ml of 15% potassium hydroxide solution was added dropwise to the solution under rapid stirring, and the reaction was stirred at room temperature for 10-15 hours. Afterwards, the reaction solution was poured into 150 ml of water, and the resulting solid was filtered under reduced pressure, washed with water several times, and dried at room temperature. Recrystallized from ethanol-acetone mixed solvent and dried in vacuum to obtain a red solid with a yield of 68%.

[0043] 1 H NMR (300MHz, CDCl 3 / TMS)δ:1.67-1.71(m,14H),2.30(t,J=5.4Hz,4H),4.86-4.96(m,2H),6.50(d,J=12.0,15.3Hz,1H),6.55 (d,J=15.3Hz,1H),7.01-7.25(m,10H),7.32-7.43(m,6H),7.49(d,J=7.8Hz,2H),7.53(d,J=8.4Hz, 2H); 13 C NMR (1...

Embodiment 2

[0044] Example 2: 3,5-bis(3-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)allylidene)cyclohexanone (I) preparation:

[0045] In a 250 ml round bottom flask, cyclohexanone (1 mmol) and 3-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)acrolein (2.2 mmol) Dissolve in 50 ml of ethanol or methanol, add 20 ml of 20% sodium hydroxide solution dropwise to the solution under rapid stirring, and react with stirring at room temperature for 10-15 hours. Afterwards, the reaction solution was poured into 150 ml of water, and the resulting solid was filtered under reduced pressure, washed with water several times, and dried at room temperature. Recrystallized from ethanol-acetone mixed solvent and dried in vacuum to obtain a red solid with a yield of 72%. ESI-MS m / z:677.3(M+H) + .

Embodiment 3

[0046] Example 3: 3,5-bis(3-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)allylidene)cyclohexanone (I) Fluorescence performance test

[0047] It is 2 * 10 that the compound of embodiment 1 is formulated into concentration -5 mol / L dichloromethane solution. Measure its ultraviolet absorption spectrum on a HORIBA Jobin Yvon Aqualog absorption and three-dimensional fluorescence scanning spectrometer with a 1 cm fluorescent cell, and measure its fluorescence spectrum on a Perkin Elmer LS-55 fluorescence spectrophotometer, the results are as follows figure 1 and figure 2 shown.

[0048] It is 2 * 10 that the compound of embodiment 1 is formulated into concentration -4 mol / L dichloromethane solution, with the femtosecond Ti of 800nm ​​wavelength: sapphire laser has measured the up-conversion luminescence characteristic of embodiment 1 molecule, and its up-conversion fluorescence spectrum sees image 3 .

[0049] Depend on figure 1 It can be seen that the molecules of Example...

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Abstract

The invention discloses a fluoro phenylindole compound which adopts a structure shown in formula I, application of the fluoro phenylindole compound as a red organic luminescent material, and a preparation method of the fluoro phenylindole compound. The fluoro phenylindole compound is obtained through a reaction between cyclohexanone and 3-(3-(4-fluorophenyl)-1-isopropyl-1H-indole-2-yl) acrolein under an alkaline condition. The preparation method is simple to operate, convenient for synthesis and easy for purification; the obtained fluoro phenylindole compound is stable in structure and can be utilized for fluorescence conversion on a strong red color displayed under 800-nm laser excitation, thereby having potential application values in such fields as luminescent equipment, anti-counterfeit technologies, laser dye and fluorescence sensing; the research field of the fluoro phenylindole compound is expanded.

Description

[0001] Technical field: [0002] The invention relates to the technical field of organic luminescent materials, in particular to a fluorophenylindole compound, its application as a red organic luminescent material and its preparation method. [0003] Background technique: [0004] Organic light-emitting materials are widely used in many fields such as optoelectronics, photovoltaic cells, and fluorescent sensors. The most prominent feature of organic light-emitting materials is that they can convert various forms of absorbed energy into light radiation. With the rapid development of modern science and technology, the application fields of organic light-emitting materials continue to expand, and it is urgent to develop organic light-emitting materials with high efficiency, low price, adjustable wavelength and excellent performance to meet the needs of the current optoelectronic technology field. [0005] Up-conversion fluorescent materials can emit visible light or even ultraviol...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/12C09K11/06
CPCC07D209/12C09K11/06C09K2211/1029
Inventor 陈智勇马艳芳孙一峰汪昭玮宋玉梅何建强张中强
Owner INSTITUTE OF ANALYSIS GUANGDONG ACADEMY OF SCIENCES (CHINA NATIONAL ANALYTICAL CENTER GUANGZHOU)
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