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Luminogens for biological applications

A compound and donor technology, applied in the field of red fluorescent AIE light-emitting materials, can solve the problems of weakening the performance and quenching of conventional red light-emitting bodies

Active Publication Date: 2019-10-08
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, these designed molecules are susceptible to the aggregation-induced quenching (ACQ) effect in the aggregated state, which severely impairs the performance of conventional red emitters in related applications.

Method used

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  • Luminogens for biological applications
  • Luminogens for biological applications
  • Luminogens for biological applications

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0216] Preparation of AIE quantum dots

[0217] Typically, 1 mg AIEgen and 5 mg DSPE-PEG-Biotin are dissolved in 1 mL chloroform. Subsequently, 9 mL of Milli-Q water was added to the chloroform solution and sonicated for 10 minutes at room temperature using a microtip probe sonicator (XL2000, Misonix Incorp, USA) with an output power of 18 W. The mixture was stirred overnight under nitrogen flow until complete evaporation of chloroform. A clear solution was obtained and filtered through a 0.45 μm microfilter to form AIE quantum dots.

[0218] Cell Culture and Staining

[0219] Cell culture: in 5% CO 2 HeLa cells were cultured in MEM containing 10% FBS and antibiotics (100 units / mL penicillin and 100 μg / mL streptomycin) in a humidity incubator at 37°C. All media were supplemented with 10% heat-inactivated FBS, 100 units / mL penicillin and 100 μg / mL streptomycin. Cells were pre-cultured until confluence prior to experimentation.

[0220] Cell Imaging: HeLa cells were grown ...

Embodiment

[0253] Synthesis of MTPE-TP

[0254] The synthesis of MTPE-TP is shown in Scheme 1 below.

[0255] Scheme 1: Synthetic route of MTPE-TP

[0256]

[0257] 4,4'-Dimethoxybenzophenone (20 mmol, 4.84 g), 4-bromobenzophenone (24 mmol, 6.26 g) and zinc powder (80 mmol, 5.2 g) were added to a 500 mL round bottom flask middle. The flask was then evacuated under vacuum and flushed three times with dry nitrogen. After adding 250 mL of anhydrous THF, the mixture was cooled to −10 °C and TiCl was added dropwise4 (7.7 mL, 70 mmol) was stirred for 30 minutes. The mixture was heated to reflux and stirred for 12 hours. After cooling to room temperature, the reaction was quenched with 1M HCl solution, 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 residue was purified by silica gel column chromatography using dichloromethane / hexane (v / v 1:5) as eluent to give 4,4'-(2-(4-...

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Abstract

A compound comprises a donor and an acceptor, wherein at least one donor ( "D" ) and at least one acceptor ( "A" ) may be arranged in an order of D-A; D-A-D; A-D-A; D-D-A-D-D; A-A-D-A-A; D-A-D-A-D; and A-D-A-D-A. The compound may be selected from the group consisting of: MTPE-TP, MTPE-TT, TPE-TPA-TT, PTZ-BT-TPA, NPB-TQ, TPE-TQ-A, MTPE-BTSe, DCDPP-2TPA, DCDPP-2TPA4M, DCDP-2TPA, DCDP-2TPA4M, TTS, ROpen-DTE-TPECM, and RClosed-DTE-TPECM. The compound may be used as a probe and may be functionalized with special targeted groups to image biological species. As non-limiting examples, the compound maybe used in cellular cytoplasms or tissue imaging, blood vessel imaging, in vivo fluorescence imaging, brain vascular imaging, sentinel lymph node mapping, and tumor imaging, and the compound may be used as a photoacoustic agent.

Description

[0001] Cross References to Related Applications [0002] This patent application claims U.S. Provisional Patent Application No. 62 / 498,093, filed December 15, 2016, U.S. Provisional Patent Application No. 62 / 602,531, filed April 27, 2017, U.S. Provisional Patent Application No. 62 / 602,531, filed September 6, 2017 Priority to Patent Application No. 62 / 605,977; all applications filed by the present inventors and incorporated herein by reference in their entirety. technical field [0003] The subject matter of the present invention relates primarily to organic chemistry, photophysics and biology. In particular, the subject of the present invention relates to design strategies and applications for the development of luminescent materials and aggregation-induced emission (AIE) luminescent materials (AIEgens) for biological applications. In particular, the subject of the present invention relates to red fluorescent AIE luminescent materials with high brightness, large Stokes shift,...

Claims

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Application Information

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IPC IPC(8): C07D241/24C07D487/02C07D513/02C07D515/02C07D517/02C09K11/00H01L51/50
CPCC07D241/24C07D417/14C07D487/02C07D495/04C07D513/02C07D285/14C07D517/02C09K11/06A61K49/0023
Inventor 唐本忠齐迹陈明秦玮张鹏飞
Owner THE HONG KONG UNIV OF SCI & TECH
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