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Organic long afterglow material with photoactivation characteristic as well as preparation method and application thereof

A technology of long afterglow materials and organic materials, applied in the direction of luminescent materials, organic chemistry, chemical instruments and methods, etc., to achieve the effect of mild preparation conditions and simplified steps

Active Publication Date: 2020-08-25
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] So far, a series of organic long afterglow materials have been developed. These organic long afterglow materials can immediately observe the ultra-long luminescence after the excitation light is irradiated and the light source is turned off. , that is, there are only a few examples of organic long afterglow materials with photoactivation properties. For example, in 2018, Academician Huang Wei’s team designed and synthesized a series of dynamic ultra-long organic phosphorescent molecules. The molecules are gradually activated under the stimulation of ultraviolet light, and the lifetime ranges from 1.8 Milliseconds gradually increased to 1.33 seconds, but from the perspective of the preparation cost of the material and the excitation lifetime of the material itself, there is still a lot of room for improvement

Method used

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  • Organic long afterglow material with photoactivation characteristic as well as preparation method and application thereof
  • Organic long afterglow material with photoactivation characteristic as well as preparation method and application thereof
  • Organic long afterglow material with photoactivation characteristic as well as preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0044] Embodiment 1: the preparation method of THPO

[0045] The chemical structural formula of THPO is as follows:

[0046]

[0047] Synthesis of THPO: triphenylphosphine (5g) was mixed with CH 2 Cl 2 Dissolve and place in an ice-water bath at 0°C, slowly add H 2 o 2 (5 mL), then stirred at room temperature for 2-4 hours. water and CH 2 Cl 2 Extract three times, collect the organic phase and wash with anhydrous Na 2 SO 4 Drying from water, followed by distillation under reduced pressure to remove the solvent gave THPO as a white powder. Structural characterization of compound THPO: 1 H NMR(400MHz, DMSO,δ):7.66–7.52(m,15H). 13 C NMR (101MHz, DMSO, δ): 133.25, 132.23, 132.04, 132.02, 131.53, 131.43, 128.82, 128.70. 31P NMR (DMSO, δ): 25.53.

[0048] Concrete synthetic route is as follows:

[0049]

Embodiment 2

[0050] Embodiment 2: the preparation method of TFPO

[0051] The chemical structural formula of TFPO is as follows:

[0052]

[0053] Synthesis of TFPO: in N 2 Dissolve 1-fluoro-4-bromobenzene (5g) in 40mL ultra-dry tetrahydrofuran under protection, and put it in a Dewar flask at -78°C; add n-BuLi (17.9mL) after 10min and stir for 1h, then add Phosphine trichloride (0.82mL), raised to room temperature, stirred for 8-12 hours; added water (20mL) to quench butyllithium, then distilled under reduced pressure to remove tetrahydrofuran; followed by water and CH 2 Cl 2 Extract three times, collect the organic phase and wash with anhydrous Na 2 SO 4 Remove water and dry, then distill under reduced pressure, remove solvent; Purify by column chromatography at last, obtain white powder; White powder is washed with CH 2 Cl 2 Dissolve and place in an ice-water bath at 0°C, slowly add H 2 o 2 (5 mL), then stirred at room temperature for 2-4 hours. water and CH 2 Cl 2 Extract ...

Embodiment 3

[0056] Example 3: TOCH 3 The preparation method of PO

[0057] TOCH 3 The chemical structural formula of PO is as follows:

[0058]

[0059] TOCH 3 Synthesis of PO: in N 2 Dissolve 4-bromoanisole (5g) in 40mL ultra-dry tetrahydrofuran under protection, and put it in a Dewar flask at -78°C; add n-BuLi (16.7mL) after 10min and stir for 1h, then add trichloro Phosphine (0.77mL), raised to room temperature, stirred for 8-12 hours; added water (20mL) to quench butyllithium, then distilled under reduced pressure to remove tetrahydrofuran; followed by water and CH 2 Cl 2 Extract three times, collect the organic phase and wash with anhydrous Na 2 SO 4 Remove water and dry, then distill under reduced pressure, remove solvent; Purify by column chromatography at last, obtain white powder; White powder is washed with CH 2 Cl 2 Dissolve and place in an ice-water bath at 0°C, slowly add H 2 o 2 (5 mL), then stirred at room temperature for 2-4 hours. water and CH 2 Cl 2 Extr...

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Abstract

The invention discloses an organic long afterglow material with photoactivation characteristic, and a preparation method and application thereof. The chemical structure of the material has a general formula; and R in the formula is H, F, OCH3. According to the invention, the series of compounds are prepared by taking a triphenylphosphine oxide derivative as a research object and connecting different substituents to three benzene ring para-positions of triphenylphosphine oxide. after controlling of the ultraviolet irradiation time, the phosphorescence service life and the intensity of the series of materials are obviously improved. And in combination with different dynamic adjustability, multiple information encryption applications are realized.

Description

technical field [0001] The invention belongs to the technical field of organic optoelectronic functional materials, and in particular relates to an organic long afterglow material with photoactivation properties and its application in the field of information encryption. Background technique [0002] Long afterglow material is a photoluminescent material with a long-life excited state, which can absorb the energy of excitation light and continue to emit light for more than 0.1 seconds after the excitation stops. The naked eye can distinguish its light emission well. In recent years, long afterglow materials have been widely used in display, emergency signal lights, data encryption, and biological imaging because of their rich excited states and long luminous lifetime. At present, inorganic materials with long-lived excited state properties have achieved sufficient development, but their disadvantages such as harsh processing conditions, scarcity of material sources, and heav...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/53C09K11/06
CPCC07F9/5325C09K11/06C09K2211/1014
Inventor 马云陆金玉佘鹏飞赵强刘淑娟
Owner NANJING UNIV OF POSTS & TELECOMM
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