Fluoro phenylindole compound, application of fluoro phenylindole compound as red organic luminescent material, and preparation method of fluoro phenylindole compound

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

Technical field:

[0001] 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. Background technique:

[0002] 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.

[0003] Up-conversion fluorescent materials can emit visible light or even ultraviolet light under ...

Examples

Embodiment 1

[0036]Example 1: 3,5-bis(3-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)allylidene)cyclohexanone (I) preparation:

[0037] 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%.

[0038] 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 (12...

Embodiment 2

[0039] Example 2: 3,5-bis(3-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)allylidene)cyclohexanone (I) preparation:

[0040] 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

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

[0042] 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.

[0043] 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 .

[0044] Depend on figure 1 It can be seen that the molecules of Example...

Technical field:

[0001] 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. Background technique:

[0002] 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.

[0003] Up-conversion fluorescent materials can emit visible light or even ultraviolet light under ...

Examples

Embodiment 1

[0036]Example 1: 3,5-bis(3-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)allylidene)cyclohexanone (I) preparation:

[0037] 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%.

[0038] 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 (12...

Embodiment 2

[0039] Example 2: 3,5-bis(3-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)allylidene)cyclohexanone (I) preparation:

[0040] 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

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

[0042] 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.

[0043] 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 .

[0044] Depend on figure 1 It can be seen that the molecules of Example...

Images