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O,O two-tooth type organic boron difluoride fluorescent dye and preparation method thereof

A technology of fluorescent dyes and boron difluoride, which is applied in the field of organic boron difluoride fluorescent dyes and its preparation, to achieve the effects of large molar extinction coefficient, saving manpower and material resources, and easy availability of raw materials

Inactive Publication Date: 2014-04-02
张庆峰
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

It shows that the current research on organic boron difluoride fluorescent dyes with solid fluorescence is still in the preliminary exploration stage, and further research is needed in order to provide a wider range of solid-state fluorescent compounds with different fluorescent colors

Method used

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  • O,O two-tooth type organic boron difluoride fluorescent dye and preparation method thereof
  • O,O two-tooth type organic boron difluoride fluorescent dye and preparation method thereof
  • O,O two-tooth type organic boron difluoride fluorescent dye and preparation method thereof

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Experimental program
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Embodiment 1

[0037] An O, O bidentate type organic boron difluoride fluorescent dye, this kind of fluorescent dye is represented as compound 1 in this embodiment 1, and the structural formula of compound 1 is:

[0038]

[0039] The method for preparing the compound 1 is as follows: put 2-propionyl indanone (5 mmol, 0.94 g) into a 50 mL two-neck flask at room temperature, and add anhydrous dichloromethane (5 mL) solution. After nitrogen purging for 2 minutes, triethylamine (30mmol, 5mL) and boron trifluoride ether (35mmol, 5mL) were injected into the reaction solution with a 10mL syringe. After reacting for 2 h at the reflux temperature of dichloromethane, the reaction was quenched with water. Extract with dichloromethane 2 to 3 times, and combine the organic phases. anhydrous Mg 2 SO 4 The organic phase is dried. Finally, after the organic phase was spin-dried in vacuum, the obtained crude product was separated and purified by a chromatographic column of 30 times its weight in silic...

Embodiment 2

[0049] The second O, O bidentate organic boron difluoride fluorescent dye, this kind of fluorescent dye is represented as compound 2 in this embodiment, and the structural formula of compound 2 is:

[0050]

[0051] The method for preparing the compound 2 is as follows: at room temperature, put 2-butyryl indanone (5 mmol, 1.01 g) into a 50 mL two-neck flask, and add anhydrous dichloromethane (5 mL) solution. After nitrogen purging for 2 minutes, triethylamine (30mmol, 5mL) and boron trifluoride ether (35mmol, 5mL) were injected into the reaction solution with a 10mL syringe. After reacting for 2 h at the reflux temperature of dichloromethane, the reaction was quenched with water. Extract with dichloromethane 2 to 3 times, and combine the organic phases. anhydrous Mg 2 SO 4 The organic phase is dried. Finally, after the organic phase was spin-dried in vacuo, the obtained crude product was separated and purified by a chromatographic column of 30 times its weight in silica...

Embodiment 3

[0061] The second O, O bidentate organic boron difluoride fluorescent dye, this kind of fluorescent dye is represented as compound 3 in this embodiment, and the structural formula of compound 3 is:

[0062]

[0063] The method for preparing the compound 3 is as follows: at room temperature, put 2-cyclohexylindanone (5 mmol, 1.21 g) into a 50 mL two-neck flask, and add anhydrous dichloromethane (5 mL) solution. After nitrogen purging for 2 minutes, triethylamine (30mmol, 5mL) and boron trifluoride ether (35mmol, 5mL) were injected into the reaction solution with a 10mL syringe. After reacting for 2 h at the reflux temperature of dichloromethane, the reaction was quenched with water. Extract with dichloromethane 2 to 3 times, and combine the organic phases. anhydrous Na 2 SO 4 The organic phase is dried. Finally, after the organic phase was spin-dried in vacuo, the obtained crude product was separated and purified by a chromatographic column of 30 times its weight in sili...

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Abstract

The invention discloses an O,O two-tooth type organic boron difluoride fluorescent dye. The dye is the compound shown in the structural general formula I in the specification and is prepared by complexing a beta-dicarbonyl compound and boron trifluoride diethyl ether. The dye has the advantages of simplicity in reaction operation, easiness in obtaining reaction reagents and high product yield. The prepared red fluorescent dye in the general formula I has the characteristic of fluorescence emission in both solution and solid states and can be used for preparing fluorescent probes, OLED (organic light emitting diode) display materials and dye-sensitized solar cells. In particular, the dye also has the characteristic of fluorescence emission in the solid state, and the characteristic greatly widens the application range of the organic boron fluorescent dye.

Description

technical field [0001] The invention relates to an organic boron difluoride fluorescent dye and a preparation method thereof, in particular to an organic boron difluoride fluorescent dye with 2-acyl indanone derivatives as ligands. Background technique [0002] The empty p orbitals of boron atoms are easy to attract π electrons, so that the system undergoes p-π type charge transfer. Organic boron difluoride compounds are a very important kind of fluorescent dyes, because they contain boron atoms and large π-conjugated systems, so they have the characteristics of large intramolecular charge transfer and rigid structure. According to different coordination atoms, organic boron difluoride fluorescent dyes can be divided into three types: N, N bidentate, N, O bidentate, O, O bidentate (Org.Lett., 2010, 12, 4010; Org.Lett.,2012,14,1528;Angew.Chem.Int.Ed.2011,50,12214;Org.Lett.,2011,13,6544;Org.Lett.,2010,12,1272;J.Am Chem.Soc., 2008, 130, 4089. J.Am.Chem.Soc., 2010, 132, 13992;...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B57/00C09K11/06
Inventor 孔凯明
Owner 张庆峰
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