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A kind of tetraphenylene isomer with aggregation-induced luminescence and supramolecular polymerization properties, preparation method and application thereof

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

Active Publication Date: 2021-11-16
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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  • A kind of tetraphenylene isomer with aggregation-induced luminescence and supramolecular polymerization properties, preparation method and application thereof
  • A kind of tetraphenylene isomer with aggregation-induced luminescence and supramolecular polymerization properties, preparation method and application thereof
  • A kind of tetraphenylene isomer with aggregation-induced luminescence and supramolecular polymerization properties, preparation method and application thereof

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preparation example Construction

[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 tetraphenylethylene isomer with aggregation-induced luminescence and supramolecular polymerization properties and its preparation method and application. )-1,2-stilbene is added to the dichloromethane solution of 2-ureido-4[1H]-pyrimidinone precursor. The present invention successfully synthesizes uracil-modified cis-trans isomers (Z)-TPE-UPy and (E)-TPE-UPy, and the isomers still retain the aggregation-induced luminescent properties of tetraphenylethylene and the uracil group Supramolecular polymerization ability, through the study of its spatial configuration, it is shown that the uracil structure forms a hole containing a heteroatom on the same side of (Z)-TPE-UPy, so that the Z-isomer can specifically detect mercury(II) ions, so (Z)‑TPE‑UPy can be widely applied to Hg 2+ Among the probes, (E)‑TPE‑UPy has excellent supramolecular polymerization ability and can be used to construct bright fluorescent fibers or photolithographic 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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Patent Type & Authority Patents(China)
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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