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Tetraphenyl ethylene isomer having aggregation-induced emission and supramolecular polymerization properties and preparation method and application thereof

A technology of aggregation-induced luminescence and tetraphenylethylene, which is applied in the fields of organic chemistry methods, luminescent materials, material excitation analysis, etc., to achieve the effect of reducing application difficulty, easy synthesis, and excellent supramolecular polymerization ability.

Active Publication Date: 2019-01-15
THE HONG KONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At this stage, there are many supramolecular polymers based on tetraphenylethylene, but the supramolecular polymers and applications based on pure Z or E configuration tetraphenylethylene have not been reported yet.

Method used

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  • Tetraphenyl ethylene isomer having aggregation-induced emission and supramolecular polymerization properties and preparation method and application thereof
  • Tetraphenyl ethylene isomer having aggregation-induced emission and supramolecular polymerization properties and preparation method and application thereof
  • Tetraphenyl ethylene isomer having aggregation-induced emission and supramolecular polymerization properties and preparation method and application thereof

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[0043] The present invention also provides a method for preparing tetraphenylethylene isomers with aggregation-induced luminescence and supramolecular polymerization properties, characterized in that: the preparation method includes the following chemical reactions:

[0044]

[0045] Preferably in the present invention, R is figure 1 i.e. R is When (Z)-TPE-UPy and (E)-TPE-UPy) synthetic structure diagram, namely:

[0046]

specific Embodiment

[0048] Table 1. Generate five specific examples of (Z)-TPE-UPy and (E)-TPE-UPy

[0049]

[0050] As can be seen from the above table 1, when using Example 1, the yield is the highest, the total yield is as high as 86%, and the (Z)-TPE-UPy and (E)-TPE-UPy yields are relatively average; the excess of compound 2 is beneficial to the product yield rate increase.

[0051] The present invention also provides the raw material compound 1 that can meet the needs of the present invention, i.e. the production method of 1,2-(4-aminobenzene)-1,2-stilbene, the specific steps are as follows: under nitrogen protection, ice bath Conditions: Slowly add 1~12g of titanium tetrachloride (5.3~63.3mmol) to 0.5~5.9g of 4-aminobenzophenone (2.5~30mmol), 0.3~4.2g of zinc powder (5.3~65mmol) in tetrahydrofuran (80mL) Then remove the ice bath from the solution and heat the mixed solution to reflux for 5 h. After the reaction solution drops to room temperature, add saturated potassium carbonate soluti...

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Abstract

The invention discloses a tetraphenyl ethylene isomer having aggregation-induced emission and supramolecular polymerization properties, and preparation method and application thereof, a chemical reaction for generating a tetraphenyl ethylene isomer is performed by adding a compound 1,2-(4-aminobenzene)-1,2-diphenylethylene to a dichloromethane solution of a 2-carbamido-4[1H]-pyrimidone precursor.The present invention successfully synthesizes uracil-modified cis-trans isomers (Z)-TPE-UPy and (E)-TPE-UPy, and the isomers still keep the aggregation-inducing emission property of tetraphenyl ethylene and the supramolecular polymerization capability of a uracil group. The research of spatial configuration of the isomers shows that the uracil structure forms a hole containing heteroatoms on thesame side as (Z)-TPE-UPy, so that the Z-isomer can specifically detect mercury (II) ions, therefore (Z)-TPE-UPy can be widely used in Hg2+ probes, (E)-TPE-UPy has an excellent supramolecular polymerization capability, and can be used to construct highlighted fluorescent fibers or photoetching patterns.

Description

technical field [0001] The invention relates to a method for generating cis-trans isomers of organic compounds, in particular to a tetraphenylethylene isomer with aggregation-induced luminescence and supramolecular polymerization properties, a preparation method and application thereof. Background technique [0002] Molecular engineering provides a "bottom-up" approach, revealing how to manipulate the function of complex systems by changing the molecular structure to affect the packing of molecules. In order to construct different functional systems, chemists have synthesized a variety of molecules for use in chemical probes, bioimaging, photofunctional materials, and biopharmaceuticals. However, chemical modification is often time-consuming and labor-intensive. At the same time, changes in molecular structure may change the essential properties of molecules. Therefore, controlling the spatial configuration of molecules is a potential strategy for the development of new func...

Claims

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Application Information

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IPC IPC(8): C07D239/47C09K11/06G01N21/64G03F7/004
CPCC07B2200/09C07D239/47C09K11/06C09K2211/1007C09K2211/1044G01N21/6428G03F7/004
Inventor 唐本忠彭慧晴
Owner THE HONG KONG UNIV OF SCI & TECH
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