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Organic compound with long afterglow effect as well as preparation method and application of organic compound

An organic compound, long afterglow technology, applied in chemical instruments and methods, fluorescence/phosphorescence, luminescent materials, etc., can solve the problems of harsh synthesis conditions, doping inorganic rare earth materials, and complexity, and achieve convenient preparation and simple reaction conditions. Effect

Inactive Publication Date: 2017-06-23
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Technical problem to be solved: the purpose of the present invention is to overcome the harsh and complicated synthesis conditions of existing inorganic afterglow materials, the need to dope inorganic rare earth materials, high price and high toxicity, and to provide a 9-benzene with n-π* transition Organic compound with long afterglow effect based on carbazole as basic unit, preparation method and application thereof

Method used

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  • Organic compound with long afterglow effect as well as preparation method and application of organic compound
  • Organic compound with long afterglow effect as well as preparation method and application of organic compound
  • Organic compound with long afterglow effect as well as preparation method and application of organic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Synthesis of PhCz: First, 1 times the equivalent of carbazole, 1 to 1.5 times the equivalent of halogenated benzene, such as bromobenzene, fluorobenzene, etc., 0.44 times the equivalent of Cu (electrolytically refined copper), 4.04 times the equivalent of K 2 CO 3 Put it into a reaction vessel, use nitrobenzene as the reaction solvent, and react at 120-160°C for 12-48 hours under the protection of nitrogen. The reaction solution is distilled under reduced pressure to obtain the crude product of 9-phenylcarbazole, and the pure product is obtained by column chromatography. The rate is 85-95%.

[0026]

[0027] Its hydrogen spectrum 1 H NMR (400MHz, CDCl 3 ), δ (TMS, ppm): 8.21 (d, 2H), 7.66 (m, 4H), 7.52 (m, 5H), 7.34 (m, 2H).

[0028] figure 1 It is the steady-state and transient spectral spectra of the obtained compound, the excitation wavelength is 295nm, and the transient spectral delay time is 10ms. The insets are the physical picture (left picture) and the a...

Embodiment 2

[0031] Synthesis of pBrPhCz: First, 1 times the equivalent of carbazole, 1 to 1.5 times the equivalent of p-dihalobenzene, such as p-dibromobenzene, 0.44 times the equivalent of Cu (electrolytically refined copper), 4.04 times the equivalent of K 2 CO 3 Put it into a reaction vessel, use nitrobenzene as a reaction solvent, and react under nitrogen protection at 120-160°C for 12-48 hours. The reaction liquid is distilled under reduced pressure to obtain a crude product, and a pure product is obtained by column chromatography with a yield of 75-85%.

[0032]

[0033] Its hydrogen spectrum 1 H NMR (400MHz, CDCl 3 ), δ (TMS, ppm): 8.16 (d, 2H), 7.75 (d, 2H), 7.47 (m, 6H), 7.34 (t, 2H).

[0034] figure 1 It is the steady-state and transient spectral spectra of the obtained compound, the excitation wavelength is 295nm, and the transient spectral delay time is 10ms. The insets are the physical picture (left picture) and the afterglow picture (right picture) of the correspondin...

Embodiment 3

[0037] Synthesis of mBrPhCz: First, 1 times the equivalent of carbazole, 1 to 1.5 times the equivalent of m-dihalobenzene, such as m-dibromobenzene, etc., 0.44 times the equivalent of Cu (electrolytic refined copper), 4.04 times the equivalent of K 2 CO 3 Put it into a reaction vessel, use nitrobenzene as a reaction solvent, and react under nitrogen protection at 120-160°C for 12-48 hours. The reaction liquid is distilled under reduced pressure to obtain a crude product, and a pure product is obtained by column chromatography with a yield of 75-85%.

[0038]

[0039] Its hydrogen spectrum 1 H NMR (400MHz, CDCl 3 ), δ (TMS, ppm): 8.30 (d, 2H), 7.90 (s, 1H), 7.71 (d, 1H), 7.62 (m, 8H).

[0040] figure 1It is the steady-state and transient spectral spectra of the obtained compound, the excitation wavelength is 295nm, and the transient spectral delay time is 10ms. The insets are the physical picture (left picture) and the afterglow picture (right picture) of the correspondi...

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Abstract

The invention discloses an organic compound with a long afterglow effect as well as a preparation method and application of the organic compound. The organic compound has a structural formula as follows: the formula is shown in the description; 9-phenylcarbazole with n-pi* is used as a basic unit, and a meta-position and a para-position of phenyl are modified; after modification, different 9-phenylcarbazole derivatives are obtained; a test shows that the fluorescence lifetime of the compound can reach 100ms or more. The compound provided by the invention has the characteristics of simple synthesis method, easiness of being purified, adjustable luminescent spectrum, flexibility, no need of doping inorganic rare-earth materials, cheap price, low toxicity and the like, and can be widely to various fields including biological imaging, disease diagnosis, optical counterfeiting prevention and the like.

Description

technical field [0001] The invention belongs to the technical field of organic afterglow luminescent materials, and specifically relates to an organic compound with long afterglow effect using n-π* transition 9-phenylcarbazole as a basic unit, a preparation method and application thereof. Background technique [0002] Long afterglow luminescent materials are referred to as long afterglow materials, also known as light-storing luminescent materials and luminescent materials. Substances that can continue to emit light after the excitation stops can store energy in energy traps, and have broad application prospects. [0003] Inorganic long afterglow materials are one of the earliest materials to be researched and applied. Many natural ores have long afterglow luminescence characteristics and are used to make various items, such as "luminous cups" and "luminous pearls". Traditional inorganic afterglow materials have many disadvantages: 1) The synthesis conditions are harsh and ...

Claims

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Application Information

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IPC IPC(8): C07D209/82C09K11/06G01N21/64
CPCC07D209/82C09K11/06C09K2211/1007C09K2211/1029G01N21/64
Inventor 陈润锋袁杰黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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