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

An ultra-long-life, room-temperature phosphorescence technology, used in security and biological imaging applications, anti-counterfeiting, preparation of bisamide compounds from carbazole and diacyl chloride compounds, can solve problems such as limited applications, and achieve easy post-processing , the effect of high quantum efficiency and long phosphorescence lifetime

Active Publication Date: 2022-08-05
SHANGHAI JIAOTONG 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 and preparation method and application thereof
  • Bisamide type ultra-long-life room temperature phosphorescent compound and preparation method and application thereof
  • Bisamide type ultra-long-life room temperature phosphorescent compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Preparation of compound DCED

[0041]

[0042] 3.83g of sodium hydride (95.59mmol, 60% dispersed in kerosene) was added to a 250ml two-necked round bottom flask, 8g of carbazole (47.84mmol) was dissolved in 120ml of redistilled tetrahydrofuran solution and added to the flask, stirred for about half an hour , 6.07ml (71.77mmol) of oxalyl chloride reagent was added 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, distilled water was added to the flask to quench, and the mixture was extracted with dichloromethane / saturated brine, and the organic layer was dried over anhydrous sodium sulfate overnight, filtered with suction, and the organic solvent was removed by rotary evaporation. The crude product was separated and purified by silica gel column chromatography (the volume ratio of the eluent was DCM / PE=1:10-1:2) to obtain 3.95 g of white solid po...

Embodiment 2

[0047] Preparation of compound o-PBCM

[0048]

[0049] The specific synthesis steps are similar to the DCED synthesis steps. In a 250ml two-necked round-bottomed flask, 3.83g of sodium hydride (95.59mmol, 60% dispersed in kerosene) was added, 8g of carbazole (47.84mmol) was dissolved in 120ml of redistilled tetrahydrofuran solution and the Added to the flask, and after stirring for about half an hour, 10.54 mL (98%, 71.77 mmol) of phthaloyl chloride reagent was added 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, distilled water was added to the flask to quench, and the mixture was extracted with dichloromethane / saturated brine, and the organic layer was dried over anhydrous sodium sulfate overnight, filtered with suction, and the organic solvent was removed by rotary evaporation. The crude product was separated and purified by silica gel column ch...

Embodiment 3

[0054] Preparation of compound m-PBCM

[0055]

[0056] 2.39g of sodium hydride (59.80mmol, 60% dispersed in kerosene) was added to a 500ml two-necked round-bottomed flask, 5g of carbazole (29.90mmol) was dissolved in 120ml of redistilled tetrahydrofuran solution and added to the flask, stirred for about half an hour , 9.11 g (44.85 mmol) of isophthaloyl chloride was dissolved in 70 ml 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, distilled water was added to the flask to quench, and the mixture was extracted with dichloromethane / saturated brine, and the organic layer was dried over anhydrous sodium sulfate overnight, filtered with suction, and the organic solvent was removed by rotary evaporation. The crude product was separated and purified by silica gel column chromatograph...

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Abstract

The invention relates to bisamide ultra-long-life room-temperature phosphorescent compounds and a preparation method and application thereof. The provided four ultra-long-life pure organic room temperature phosphorescent molecules are all prepared by N acylation of carbazole and acid chloride in one step, and DCED, o Four compounds, ‑PBCM, m‑PBCM and p‑PBCM, were recrystallized in ethanol solution to obtain single crystals of DCED, o‑PBCM and p‑PBCM, as well as the flocculent after recrystallization of m‑PBCM thing. Compared with the prior art, the four substances obtained by the present invention all have the property of ultra-long-life room temperature phosphorescence, especially the compound m-PBCM obtained by the present invention has a phosphorescence life of 710.6 ms at room temperature. Applied in the biological field, the m‑PBCM nanoparticle solution was injected into the right back of nude mice for afterglow imaging, and its signal-to-noise ratio was as high as 428; the injection into the forepaw of nude mice can also be used as an effective afterglow contrast agent, with excellent sensitivity and The signal-to-noise ratio precisely illuminates its axillary lymph nodes.

Description

technical field [0001] The invention relates to a developing molecule, in particular to a preparation method for preparing bisamide compounds from carbazole and diacid chloride compounds and their application in anti-counterfeiting, security and biological imaging. Background technique [0002] Due to their unique properties such as ultra-long lifetime, room temperature phosphorescent materials can be used in the fields of organic light-emitting diodes (OLEDs), biological imaging, chemical sensors, optics and anti-counterfeiting technologies. For example, when applied to biological imaging, due to its long-life nature, there is still a certain degree of afterglow after turning off the UV light, which can eliminate the need for illumination and avoid the interference of nanosecond tissue autofluorescence. Clearer and more reliable biological imaging with high noise ratio. Most of the current ultra-long-life room temperature phosphorescent materials are mainly limited to inor...

Claims

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Application Information

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Patent Type & Authority Patents(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 JIAOTONG UNIV
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