Organelle-targeted aggregation-induced emission material and preparation method thereof

A technology of aggregation-induced luminescence and organelles, which is applied in luminescence materials, chemical instruments and methods, and material analysis through optical means, can solve the problems of poor luminescence performance in the aggregated state, achieve good specific imaging performance, low preparation cost, The effect of simple synthesis and purification process

Active Publication Date: 2020-01-10
XI AN JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to solve the problem of poor luminescent performance of traditional organic fluorescent materials in the aggregated state, and to achieve specific targeted imaging in cells, the purpose of the present invention is to provide a class of organelle-targeted aggregation-induced luminescent materials and a preparation method thereof; In the solution state, the constructed aggregation-induced luminescent materials show more excellent fluorescence emission properties after forming aggregates; at the same time, this type of material also has better biocompatibility, and can be better applied to lipid droplets and mitochondria, etc. The specific targeted imaging of organelles provides a reliable method and approach for further dynamic observation of cell states and understanding of interactions between intracellular organelles, etc.

Method used

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  • Organelle-targeted aggregation-induced emission material and preparation method thereof
  • Organelle-targeted aggregation-induced emission material and preparation method thereof
  • Organelle-targeted aggregation-induced emission material and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The organelle-targeted aggregation-induced luminescent material of this embodiment has the following structural formula (I):

[0034]

[0035] The preparation method of the aggregation-induced luminescent material of this embodiment includes the following steps:

[0036] Step 1: Using 4-boronate triphenylamine and 2,5-dibromopyridine as raw materials, fully dissolved in toluene solution, adding potassium carbonate solution and ethanol solvent, and using tetrakistriphenylphosphine palladium as the reaction catalyst, After reacting for 20 hours under nitrogen protection at 90°C, the target compound (I) was obtained after quenching with water, extraction with organic solution, washing, solvent removal and column chromatography purification.

[0037] The molar ratio between the 4-boronate triphenylamine and 2,5-dibromopyridine is 2.5:1, the molar ratio of potassium carbonate to 2,5-dibromopyridine is 6:1, tetratriphenyl The molar ratio of phosphine palladium to 2,5-dibr...

Embodiment 2

[0044] The organelle-targeted aggregation-induced luminescent material of this embodiment has the following structural formula (II):

[0045]

[0046] The preparation method of the aggregation-induced luminescent material of this embodiment includes the following steps:

[0047] Step 1: Using 4-boronate-4',4'-dimethoxytriphenylamine and 4,7-dibromo-2,1,3-benzothiadiazole as raw materials, fully dissolve in toluene solution Afterwards, potassium carbonate solution and ethanol solvent were added, and tetrakistriphenylphosphine palladium was used as the reaction catalyst. After reacting for 24 hours under nitrogen protection conditions at 85°C, it was quenched by adding water, extracted with organic solution, washed, removed solvent and column chromatography After purification, the target compound (II) is obtained.

[0048] The molar ratio between the 4-boronate-4',4'-dimethoxytriphenylamine and 4,7-dibromo-2,1,3-benzothiadiazole is 2.5:1, The molar ratio of potassium carbon...

Embodiment 3

[0055] The organelle-targeted aggregation-induced luminescent material of this embodiment has the following structural formula (III):

[0056]

[0057] The preparation method of the aggregation-induced luminescent material of this embodiment includes the following steps:

[0058] Using the product of Example 1 and methyl iodide as raw materials, add toluene to fully dissolve it, and heat at 88°C for 18 hours. After removing the toluene solvent, sodium hexafluorophosphate was added and fully dissolved in acetonitrile. After stirring at room temperature for 18 hours, washing with water, removing the solvent under reduced pressure and recrystallization, the target fluorescent product (III) was obtained.

[0059] The molar ratio between the product in Example 1 and methyl iodide is 1:2.5; the molar ratio between the product in Example 1 and sodium hexafluorophosphate is 1:10.

[0060] The reaction formula is:

[0061]

[0062] The specific operation is: add the product of...

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Abstract

The invention discloses an organelle-targeted aggregation-induced emission material and a preparation method thereof. The method comprises the following steps: 1) taking a triphenylamine borate and anaryl bromide compound as raw materials, fully and completely dissolving in a toluene solution, adding a potassium carbonate solution and ethanol solvent, taking tetrakis (triphenylphosphine) palladium as a reaction catalyst, carrying out nitrogen reaction, adding extraction, washing, removing of solvent, and carrying out column chromatography purification to obtain a target material; wherein whenthe aryl bromide compound in the step 1 is 2,5-dibromopyridine and 2, 5-dibromopyrazine, a product obtained in the step 1 and methyl iodide are taken as raw materials and are dissolved in toluene,heating reaction is carried out, toluene solvent is removed, then sodium hexafluorophosphate and acetonitrile are added to be fully dissolved, stirring is carried out for 12-24 hours at the room temperature, and a target fluorescent product can also be obtained after water washing, solvent removal under reduced pressure and recrystallization. The preparation and purification cost is low; the producthas excellent fluorescence emission performance, and can realize specific targeting imaging performance research of a plurality of organelles in cells.

Description

technical field [0001] The invention relates to the technical field of organic fluorescent materials and biological imaging thereof, in particular to a class of cell organelle-targeted aggregation-induced luminescent materials and a preparation method thereof. Background technique [0002] Compared with inorganic fluorescent materials, organic fluorescent materials usually have excellent luminescent properties and biocompatibility, and have shown good application prospects in biomedical fields such as cell imaging. At the same time, the good structural tunability of organic fluorescent materials can also provide the possibility to further meet their in-depth applications in the field of bioimaging. However, it is worth noting that for traditional organic fluorescent materials, although they can show good luminous efficiency and brightness in a single molecular state such as a solution, their luminous brightness usually falls short in an aggregated state such as a solid state...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/38C07D285/14C09K11/06G01N21/64
CPCC07D213/38C07D285/14C09K11/06C09K2211/1014C09K2211/1029C09K2211/1051G01N21/6428G01N21/6486
Inventor 党东锋胥艳子王直申起飞赵博孟令杰
Owner XI AN JIAOTONG UNIV
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