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Aie compounds with fluorescence, photoacoustic, and raman properties

A compound and conjugation technology, applied in organic chemistry, color-changing fluorescent materials, luminescent materials, etc., can solve problems such as difficult to propose molecular criteria and difficult to obtain organic reagents

Active Publication Date: 2021-09-10
THE HONG KONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, one-for-all organic reagents capable of fluorescence, PA, and Raman imaging are elusive due to the difficulty in proposing molecular guidelines that can maximize each optical imaging property

Method used

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  • Aie compounds with fluorescence, photoacoustic, and raman properties
  • Aie compounds with fluorescence, photoacoustic, and raman properties
  • Aie compounds with fluorescence, photoacoustic, and raman properties

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0241] Synthesis and characterization of OTPA-TQ

[0242] Synthesis of 1-iodo-4-(octyloxy)benzene (2): 1-bromooctane (4.24g, 22mmol), 4-iodophenol (4.4g, 20mmol) and K 2 CO 3 (8.3 g, 60 mmol) was added to a 250 mL two necked round bottom flask and the flask was evacuated and purged 3 times with dry nitrogen. Anhydrous DMF (120 mL) was then added, and the mixture was heated to reflux and stirred for 24 hours. After cooling to room temperature, water was added, and the mixture was washed 3 times with dichloromethane. Combine the organic phases with MgSO 4 Dry, and evaporate the solvent under reduced pressure. The crude product was purified by column chromatography on silica gel using dichloromethane / hexane (v / v 1:10) as eluent to afford 1-iodo-4-(octyloxy)benzene as a colorless oil (yield 83%). 1 H NMR (400MHz, CDCl 3 ):δ7.53(d,2H),6.86(d,2H),3.90(t,2H),1.82-1.70(m,2H),1.48-1.39(m,2H),1.39-1.21(m,8H ),0.89(t,3H). 13 CNMR (100MHz, CDCl 3 ): δ159.02, 138.14, 116.94, 82...

Embodiment 2

[0244] Synthesis of 4-bromo-N,N-bis(4-(octyloxy)phenyl)aniline (4)

[0245] 4-bromoaniline (1.03g, 6mmol), 1-iodo-4-(octyloxy)benzene (4.98g, 15mmol), 1,10-phenanthroline (0.18g, 1mmol), CuI (2.12g, 0.19 mmol) and KOH (5.04 g, 90 mmol) were added to a 250 mL two necked round bottom flask. Dry toluene (50 mL) was added to the flask under nitrogen atmosphere. The flask was then evacuated and purged three times with dry nitrogen, and the mixture was heated to reflux and stirred for 24 hours. After cooling to room temperature, water was added, and the mixture was washed 3 times with dichloromethane. Combine the organic phases with MgSO 4 Dry, and evaporate the solvent under reduced pressure. The crude product was purified by column chromatography on silica gel using dichloromethane / hexane (v / v 1:6) as eluent to afford 4-bromo-N,N-bis(4-(octyloxy) as a viscous oil ) phenyl) aniline (yield 76%). 1 H NMR (400MHz, CDCl 3 ):δ7.22(d,2H),7.00(d,4H),6.79(t,6H),3.92(t,4H),1.81-1.7...

Embodiment 3

[0247] Synthesis of 4-(octyloxy)-N-(4-(octyloxy)phenyl)-N-(4-(tributylstannyl)phenyl)aniline (5)

[0248] 4-Bromo-N,N-bis(4-(octyloxy)phenyl)aniline (2.32 g, 4 mmol) was added to a 100 mL two necked round bottom flask. The flask was then evacuated and flushed three times with dry nitrogen, and anhydrous THF (50 mL) was added. The mixture was then cooled to −78° C. with a dry ice-acetone mixture and kept at this temperature for 15 minutes before adding n-butyllithium ( n BuLi, 2.5M in hexane, 1.6 mL, 4 mmol). After stirring at this temperature for 2 hours, tri-n-butyltin chloride (1.1 mL, 4 mmol) was added, and the mixture was slowly warmed to room temperature and stirred overnight. After that, water was added to quench the reaction, and the mixture was extracted three times with dichloromethane. Combine the organic phases with MgSO 4 Dry, and evaporate the solvent under reduced pressure. The crude product was used without further purification.

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Abstract

The present subject matter relates to fluorescent compounds that have aggregation-induced emission (AIE) characteristics. The compounds exhibit boosted fluorescence, photoacoustic (PA) properties, and Raman properties. The compounds, in nanoparticle form, can generate high fluorescence, PA, and Raman signals in aqueous environments. The compounds can be used to identify tumors at different surgical stages and improve cancer surgery outcomes.

Description

[0001] cross reference [0002] This application claims priority to the present inventors' Provisional U.S. Patent Application No. 62 / 919,427, filed March 13, 2019, which is hereby incorporated by reference in its entirety. technical field [0003] The subject matter of the present application generally relates to a series of fluorescent compounds with aggregation-induced luminescent properties and near-infrared absorption and their use in bioimaging. Background technique [0004] Molecular motion plays a very important role in many fundamental physical and chemical processes, and it has great potential to promote the development of biomedical fields. The controllability and availability of dynamic molecular motions enable precise tunability of functional / smart materials, which is especially beneficial for precision medicine and personalized diagnosis and treatment. In particular, according to the Jablonski energy level diagram, the intramolecular motions of chromophores in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/24C07D487/02C09K11/00H01L51/50
CPCC09K11/06C09K9/02C07D513/04
Inventor 唐本忠丁丹齐迹
Owner THE HONG KONG UNIV OF SCI & TECH
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