Composition and synthesis of aggregation-induced emission materials

A technology of synthesis and luminescence, which is applied in the direction of luminescent materials, compounds of group 5/15 elements of the periodic table, analytical materials, etc., and can solve the problem of confinement effects, fluorescence quenching, and difficult detection of low-abundance molecular species in biological systems, etc. question

Active Publication Date: 2016-04-13
THE HONG KONG UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

When luminophore molecules are dispersed in aqueous media or combined with biomolecules, they tend to aggregate, which usually quenches their fluorescence, thus greatly limiting their usefulness as bioprobes
The ACQ effect can also ma

Method used

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  • Composition and synthesis of aggregation-induced emission materials
  • Composition and synthesis of aggregation-induced emission materials
  • Composition and synthesis of aggregation-induced emission materials

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[0206] In addition, the subject matter of the present application also discloses a method for synthesizing TPE derivatives with activated luminophores showing aggregation-induced luminescence, comprising the steps of: (a) adding benzoyl chloride to DBT or DBF; (b) refluxing the reaction mixture to obtain an intermediate compound; (c) subjecting the intermediate compound to a McMurry coupling reaction to obtain a TPE derivative. In some embodiments, the intermediate compound is dibenzo[b,d]thiophen-2-yl(phenyl)methanone or dibenzo[b,d]furan-2-yl(phenyl)methanone. In another embodiment, aluminum chloride or dichloromethane is added to step (a) of the synthesis process of the TPE derivative.

[0207] In one embodiment, when DBT is used in step (a), the E-isomer of STPE is formed in DCM and methanol solution, wherein in step (a) DBT is dissolved in DCM solution, methanol is gradually Dropwise into this solution. In another embodiment, when DBT is used in step (a), the Z-isomer i...

Embodiment

[0299] Preparation of TPE and its derivatives

[0300] Benzophenone, palladium activated carbon (Pd / C), zinc powder, dibenzosubrone and all benzophenone derivatives were purchased from Aldrich and used without further purification. Tetrahydrofuran (THF) was freshly distilled from sodium benzophenoneketyl under nitrogen atmosphere and used immediately.

[0301] Measured on a Bruker AV300 spectrometer using tetramethylsilane (TMS; δ=0) as internal standard in deuterated chloroform 1 H and13 CNMR spectrum. Absorption spectra were measured on a MiltonRoy Spectronic3000 array spectrophotometer. Photoluminescence was recorded on a Perkin-Elmer LS55 spectrofluorometer. High resolution mass spectra (HRMS) were recorded on a GCTpremierCAB048 mass spectrometer operated in MALDI-TOF mode. Single crystal X-ray diffraction intensity data were collected at 100K on a Bruker-Nonices SmartApex CCD diffractometer with graphite monochromatized MoKα radiation. The intensity data were proce...

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Abstract

The present subject matter relates to compositions containing and synthesis of fluorescent materials e made from tetraphenylethylene (TPE) derivative compounds exhibiting aggregation induced emission (AIE) properties. Further contemplated herein are applications for TPE derivative compounds such as electroluminescent devices since they have a high efficiency, low turn on voltage, and excellent brightness. Additionally, application of TPE derivatives exhibiting AIE properties in various fields such as OLEDs, fingerprinting and forensic technology, and various other biological and industrial sectors are discussed.

Description

[0001] related application [0002] This patent application claims priority to Provisional Patent Application No. 61 / 958,743, filed August 5, 2013 by the inventors of this application, which is hereby incorporated by reference in its entirety. technical field [0003] The subject matter of this application relates to the composition and synthesis of fluorescent materials prepared from tetraphenylethylene (TPE) derivatives exhibiting aggregation-induced emission (AIE) properties. Further considered here are applications of TPE derivatives, such as electroluminescent devices, due to their high efficiency, low turn-on voltage, and excellent brightness. Furthermore, the applications of TPE derivatives showing AIE properties in various fields such as OLEDs, forensics, latent fingerprint detection, and various other biological and industrial sectors are discussed. Background technique [0004] Electroluminescence refers to the energy absorbed by molecules subjected to an electric...

Claims

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Application Information

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IPC IPC(8): G01N21/64C09B62/343C07D207/448
CPCC07D407/06C07D409/06C09B23/105C09B23/148C09B57/00C09B57/008C07F9/58C07D307/91C07D333/76C09K11/06C09K11/07G01N33/4833H10K85/371H10K85/60H10K85/626H10K85/636H10K85/6574H10K85/6576H10K50/11C07C13/54C07C15/18C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1088C09K2211/1092C09K2211/188
Inventor 唐本忠谢你林荣业
Owner THE HONG KONG UNIV OF SCI & TECH
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