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Peripheral Modified Aggregation-Induced Luminescent Enhanced Dendrimer with Chromophore and Its Preparation Method and Application

A technology of aggregation-induced luminescence and chromophore, which is applied in the field of dendrimers and their preparation, can solve the problems of enhancing non-radiative decay process and restricting applications, and achieves the effect of suppressing non-radiative decay

Active Publication Date: 2016-05-25
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, when most organic light-emitting compounds are in high concentration or solid state, the non-radiative decay process is enhanced due to the strong interaction between molecules, resulting in an order of magnitude decrease in the luminous efficiency of the solid-state or aggregated state compared with the dilute solution, which is to a large extent limit their applications in light-emitting devices and fluorescent sensors

Method used

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  • Peripheral Modified Aggregation-Induced Luminescent Enhanced Dendrimer with Chromophore and Its Preparation Method and Application
  • Peripheral Modified Aggregation-Induced Luminescent Enhanced Dendrimer with Chromophore and Its Preparation Method and Application
  • Peripheral Modified Aggregation-Induced Luminescent Enhanced Dendrimer with Chromophore and Its Preparation Method and Application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Preparation of 0-generation tetraphenylbutadiene (hereinafter referred to as: TPBD) chromophore-modified dendrimer (D0-C12-TPBD) with dodecyldiamine as the core

[0033]

[0034] Add 3mmol of tetraphenylbutadiene (TPBD) carboxylic acid derivative TPBD-COOH and 15mL of DMSO into a 50mL two-necked flask, and then add 4.2mmol of 1-ethyl-(3-dimethylaminopropyl)carbonyl Diimine hydrochloride, 3mmol 1-hydroxybenzotriazole (HOBT). Stir the reaction at room temperature under nitrogen protection for 2h, and slowly add 20mL of 0-generation solution with dodecyldiamine as the nucleus to the reaction system dropwise. The DMSO solution of polyamide-amine dendrimer (G0-C12), the ratio of the amount of TPBD chromophore to the peripheral amine group of G0-C12 is 1.4:1, continue to stir and react for 72h, and pour the reaction solution slowly into 300mL of water, filter and wash the solid with 30mL of water, and dry the crude product in a vacuum oven at 40°C. Dissolve the solid with...

Embodiment 2

[0037] Preparation of 1-generation benzofuran naphthyridine (hereinafter referred to as: BAN) chromophore-modified dendrimer (D1-Cyclohexane-BAN) with 1,4-cyclohexanediamine as the core

[0038]

[0039] Add 3mmol of benzofurannaphthyridine (BAN) carboxylic acid derivative BAN-COOH and 15mL of DMSO into a 50mL two-neck flask, and then add 4.2mmol of 1-ethyl-(3-dimethylaminopropyl)carbonyl dicarboxylate after the solid is dissolved. Imine hydrochloride, 3 mmol 1-hydroxybenzotriazole (HOBT). Stir the reaction at room temperature under nitrogen protection for 2 hours, and slowly add 20 mL of 1-generation polyamide with cyclohexanediamine as the core in 20 mL dropwise to the reaction system - DMSO solution of amine dendrimer (G1-Cyclohexane), the ratio of the amount of BAN chromophore to the peripheral amine group of G1-Cyclohexane is 1:1, continue to stir and react for 96h, and slowly pour the reaction solution into 300mL water, filter and wash the solid with 30mL of water, an...

Embodiment 3

[0041] Preparation of 2-generation silacyclopentadiene chromophore-modified dendrimer (D2-Ph-Silole) with p-phenylenediamine as the core

[0042]

[0043] Add 3mmol of silole (Silole) carboxylic acid derivative Silole-COOH and 15mL of DMSO into a 50mL two-necked flask, and then add 4.2mmol of 1-ethyl-(3-dimethylaminopropyl)carbonyl Diimine hydrochloride, 3 mmol 1-hydroxybenzotriazole (HOBT). Stir the reaction at room temperature under nitrogen protection for 2 hours, slowly add 20 mL of 2-generation polyamide with 0.135 mmol p-phenylenediamine as the core to the reaction system dropwise - DMSO solution of amine dendrimer (G2-Ph), the ratio of Silole chromophore to G2-Ph peripheral amine group is 2:1, continue to stir and react for 96h, and slowly pour the reaction solution into 300mL water, filter and wash the solid with 30mL of water, and dry the crude product in a vacuum oven at 40°C. Dissolve the solid with 20 mL of chloroform, precipitate once in ether, filter and wash...

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Abstract

The invention discloses a dendrimer externally modified with an aggregation-induced emission enhanced chromophore as well as well as a preparation method and application thereof. The dendrimer externally modified with the aggregation-induced emission enhanced chromophore has a structure as shown in formula (I) in the specification, wherein n is an integer of 0-4; X is selected from C2-20 linear chain alkyl, C2-20 branched chain alkyl, C2-20 cyclic saturated alkyl, O(CH2CH2O)m with m not less than 2 or aryl with 6-30 carbon atoms. The functional dendrimer molecular framework of the dendrimer disclosed by the invention has biocompatibility, and can emit fluorescent light under a liquor state. The spectral properties of the functional dendrimer can change with environmental changes, so that detecting and image-forming purposes can be achieved. The invention provides a novel thought for researching and developing the novel light-function dendrimer, and promoting the application of the dendrimer in an organic light-emitting material, bio-labeling, and the like.

Description

technical field [0001] The invention relates to the technical field of organic light-emitting materials, in particular to a dendritic polymer modified by aggregation-induced emission-enhancing chromophores and a preparation method and application thereof. Background technique [0002] Organic light-emitting compounds have a wide range of applications in the fields of organic light-emitting materials, cell imaging, and biomarkers. However, when most organic light-emitting compounds are in high concentration or solid state, the non-radiative decay process is enhanced due to the strong interaction between molecules, resulting in an order of magnitude decrease in the luminous efficiency of the solid-state or aggregated state compared with the dilute solution, which is to a large extent This limits their application in light-emitting devices and fluorescence sensors. It is generally believed that the luminescence quenching phenomenon caused by the increase of concentration is cl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G83/00C09K11/06
Inventor 李嫕李鹏曾毅陈金平于天君李迎迎
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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