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Bisamide type ultra-long-life room-temperature phosphorescent compound as well as preparation method and application thereof

An ultra-long-life, room-temperature phosphorescence technology, used in security and biological imaging applications, preparation of bisamide compounds from carbazole and diacyl chloride compounds, in the field of anti-counterfeiting, can solve problems such as limited applications, and achieve easy post-processing , The synthesis steps are simple, and the effect of the spin-orbit coupling effect is enhanced.

Active Publication Date: 2019-06-14
SHANGHAI JIAO TONG UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

First, the quantum efficiencies of phosphors with reported lifetimes of more than a few hundred milliseconds are usually below 5%; in addition, stable room-temperature phosphorescence in complex and changing environments is rare, which greatly limits its use in data Applications in recording, security, and bioimaging

Method used

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  • Bisamide type ultra-long-life room-temperature phosphorescent compound as well as preparation method and application thereof
  • Bisamide type ultra-long-life room-temperature phosphorescent compound as well as preparation method and application thereof
  • Bisamide type ultra-long-life room-temperature phosphorescent compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Preparation of compound DCED

[0041]

[0042] Add 3.83g of sodium hydride (95.59mmol, 60% dispersed in kerosene) in a 250ml two-necked round-bottomed flask, dissolve 8g of carbazole (47.84mmol) in 120ml of redistilled tetrahydrofuran solution and add it to the flask, after stirring for about half an hour , add 6.07ml (71.77mmol) oxalyl chloride reagent dropwise. The reaction was carried out overnight at room temperature, and the progress of the reaction was monitored by silica gel chromatography (TLC). After the reaction was completed, distilled water was added to the flask to quench, and the liquid was extracted and separated with dichloromethane / saturated brine. The organic layer was dried over anhydrous sodium sulfate, filtered with suction, and the organic solvent was removed by rotary evaporation. The crude product was separated and purified by silica gel column chromatography (volume ratio of eluent: DCM / PE=1:10-1:2) to obtain 3.95 g of white solid powder wit...

Embodiment 2

[0047] Preparation of compound o-PBCM

[0048]

[0049] Concrete synthetic steps are similar to DCED synthetic steps, add 3.83g sodium hydride (95.59mmol, 60% are dispersed in kerosene) in 250ml two-necked round-bottomed flasks, 8g carbazole (47.84mmol) are dissolved in 120ml redistilled tetrahydrofuran solution and Add it to the flask, stir for about half an hour, then add 10.54 mL (98%, 71.77 mmol) of phthaloyl chloride reagent dropwise. The reaction was carried out overnight at room temperature, and the progress of the reaction was monitored by silica gel chromatography (TLC). After the reaction was completed, distilled water was added to the flask to quench, and the liquid was extracted and separated with dichloromethane / saturated brine. The organic layer was dried over anhydrous sodium sulfate, filtered with suction, and the organic solvent was removed by rotary evaporation. The crude product was separated and purified by silica gel column chromatography (volume ratio...

Embodiment 3

[0054] Preparation of compound m-PBCM

[0055]

[0056] Add 2.39g of sodium hydride (59.80mmol, 60% dispersed in kerosene) in a 500ml two-necked round bottom flask, dissolve 5g of carbazole (29.90mmol) in 120ml of redistilled tetrahydrofuran solution and add it to the flask, after stirring for about half an hour , 9.11g (44.85mmol) of isophthaloyl chloride was dissolved in 70ml of redistilled tetrahydrofuran solution and added dropwise to the reaction system. The reaction was carried out overnight at room temperature, and the progress of the reaction was monitored by silica gel chromatography (TLC). After the reaction was completed, distilled water was added to the flask to quench, and the liquid was extracted and separated with dichloromethane / saturated brine. The organic layer was dried over anhydrous sodium sulfate, filtered with suction, and the organic solvent was removed by rotary evaporation. The crude product was separated and purified by silica gel column chromato...

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Abstract

The invention relates to a bisamide type ultra-long-life room-temperature phosphorescent compound and a preparation method and application thereof. Four pure organic room-temperature phosphorescent molecules with ultra-long service life are prepared by one-step reaction of N acylation of carbazole and acyl chloride, and thus four compounds, namely, DCED, o-PBCM, m-PBCM and p-PBCM are obtained, andsingle crystals of three compounds DCED, o-PBCM and p-PBCM and floccules of m-PBCM after recrystallization are obtained by using a recrystallization method in an ethanol solution. Compared with the prior art, the four substances obtained by the preparation method have ultra-long service life and room-temperature phosphorescent properties, and particularly, the phosphorescent service life of the compound m-PBCM obtained by the preparation method at room temperature is up to 710.6 ms. When the compound m-PBCM is applied to the field of biology, an m-PBCM nanoparticle solution is injected to theright back of a nude mouse for afterglow imaging, and the signal-to-noise ratio of the m-PBCM nanoparticle solution reaches up to 428; after being injected into a forepaw of a nude mouse, the m-PBCMnanoparticle solution can also be used as an effective afterglow contrast agent to accurately illuminate axillary lymph nodes with excellent sensitivity and signal-to-noise ratio.

Description

technical field [0001] The invention relates to a developing molecule, in particular to a method for preparing bisamide compounds from carbazole and diacyl chloride compounds and its application in anti-counterfeiting, confidentiality and biological imaging. Background technique [0002] Due to its unique properties such as ultra-long lifespan, room-temperature phosphorescent materials can be used in organic light-emitting diodes (OLEDs), biological imaging, chemical sensors, optics, and anti-counterfeiting technology. For example, when applied to biological imaging, due to its long-lived nature, there is still a certain degree of afterglow after the ultraviolet light is turned off, which can eliminate the need for illumination and avoid the interference of nanosecond-level tissue autofluorescence. Higher noise ratio, clearer and more reliable biological imaging. At present, most ultra-long-lived room temperature phosphorescent materials are mainly limited to inorganic comp...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C09K11/06B42D25/378B42D25/387G01N21/64
Inventor 袁望章贺紫晗张永明丁丹高贺麒
Owner SHANGHAI JIAO TONG UNIV
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