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Polyethylene terephthalate (PET) type Fe<3+> fluorescent probe and preparation method and application thereof

A fluorescent probe, ethoxy technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve problems such as poor solubility, achieve low cost, good solubility, and increase solubility

Inactive Publication Date: 2013-04-17
FUZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the existing peryleneimide compounds have the problem of poor solubility

Method used

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  • Polyethylene terephthalate (PET) type Fe&lt;3+&gt; fluorescent probe and preparation method and application thereof
  • Polyethylene terephthalate (PET) type Fe&lt;3+&gt; fluorescent probe and preparation method and application thereof
  • Polyethylene terephthalate (PET) type Fe&lt;3+&gt; fluorescent probe and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] 1) Synthesis of 1-(tert-butoxycarbonyl)ethylenediamine: Dissolve 10.0 g (166.7 mmol) ethylenediamine and 6.1 g (28 mmol) di-tert-butyl dicarbonate in 400 ml dichloromethane at 0~25 The reaction was carried out at ℃ for 19 hours. After the reaction was completed, the solvent was distilled off, and the crude product was extracted with dichloromethane, and then petroleum ether-ethyl acetate (5: 1, v / v) was used as the eluent to separate the product by silica gel column chromatography. Product 4.1 g, yield rate is 90%.

[0053] 2) Synthesis of N, N ’ -Dipropargyl carbamate: Mix 11.3 g (82 mmol) of anhydrous potassium carbonate, 3.2 ml (36.2 mmol) of propyne bromide and 2.6 g (16.4 mmol) of 1-(tert-butoxycarbonyl)ethylenediamine React in 50 ml of dichloromethane at 0~25°C for 8 hours, distill off the solvent after the reaction, extract the crude product with dichloromethane, and then use petroleum ether-ethyl acetate (6: 1, v / v) as The eluent was separated by silica gel c...

Embodiment 2

[0057] The preparation method is the same as that of Example 1. In the process of (1), ethylenediamine and di-tert-butyl dicarbonate are reacted in a dichloromethane system at 0°C for 12 hours in a molar ratio of 2:1, and the other operations are the same. The yield of 1-(tert-butoxycarbonyl)ethylenediamine was 25%. In the process of (2), anhydrous potassium carbonate, bromopropyne, and 1-(tert-butoxycarbonyl)ethylenediamine are reacted in dichloromethane at 25°C for 12 hours in a molar ratio of 3:2:1. After the reaction, the solvent was distilled off, the crude product was extracted with dichloromethane, and then methanol-dichloromethane was used as the eluent to obtain the described product through silica gel column chromatography with a yield of 40%. In the process of (3), the N, N ’ - Dipropargyl carbamate, 1-azido-3, 6, 9-trioxydecane, copper sulfate pentahydrate and sodium ascorbate in a molar ratio of 1: 10: 0.1: 0.2 in tert-butyl Reaction was carried out at 25° C. fo...

Embodiment 3

[0059] The preparation method is the same as Example 1. In the process of (1), ethylenediamine and di-tert-butyl dicarbonate are reacted in a dichloromethane system for 16 hours in a molar ratio of 10:1, and the other operations are the same. 1-(tert-butyl Butoxycarbonyl) ethylenediamine yield was 60%. In the process of (2), anhydrous potassium carbonate, bromopropyne, and 1-(tert-butoxycarbonyl)ethylenediamine are reacted at a molar ratio of 10:2.5:1 in dichloromethane at 25°C for 12 hours After the reaction, the solvent was distilled off, the crude product was extracted with dichloromethane, and then methanol-dichloromethane was used as the eluent to obtain the described product through silica gel column chromatography with a yield of 45% to 50%. In the process of (3), the N, N ’ - Dipropargyl carbamate, 1-azido-3, 6, 9-trioxydecane, copper sulfate pentahydrate and sodium ascorbate in a molar ratio of 1: 2: 0.2: 0.4 in tert-butyl Reaction was carried out at 25° C. for 24 h...

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Abstract

The invention discloses a polyethylene terephthalate (PET) type Fe<3+> fluorescent probe and a preparation method and application thereof. The fluorescent probe comprises a compound which is N,N'-di(N,N'-{di{(1-(2-(2-(2-methoxy-oxethyl)oxethyl)oxethyl)ethyl)-1H-1,2,3-triazole-4-yl)methyl}azyl}-1,2-diamine)-3,4:9,10-perylene bisimide. According to the preparation method, a triethylene glycol monomethyl ether chain with an alcoxyl long chain is introduced to the periphery of a perylene tetracarboxylic acid imide large ring, so that the amphipathy and biocompatibility of the PET type Fe<3+> fluorescent probe are increased, and the application range of the PET type Fe<3+> fluorescent probe is promoted. The compound of the probe is non-toxic and harmless, has a good application prospect, is single in structure and does not have isomers, so that the product is easy to purify; and a synthetic method is relatively simple, less in side reaction, higher in yield, low in cost and favorable for industrial production, and raw materials are easy to obtain.

Description

technical field [0001] The invention belongs to the field of synthesis of organic and metal coordination compounds, in particular to a PET type Fe 3+ Fluorescent probes and their preparation methods and applications. Background technique [0002] Fe 3+ Ions play a crucial role in cell biology. It is not only a very important transition metal element in the cell system, but also an important component element of some enzymes and proteins in the human body. 3+ Ions all play an important role, and it is an indispensable element for the human body. In addition, Fe in cells 3+ Changes in ion content are criteria for judging some diseases, including certain cancers and inactivation of physiological organs. Fe 3+ Ions are also an indispensable and important constituent element in the living environment. Synthetically design an Fe that can be applied to the environment or cells 3+ Fluorescent probes are used to monitor Fe 3+ A convenient means of ions. Perylene imide compo...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D471/06G01N21/64
Inventor 刘见永陈博刘晓琼
Owner FUZHOU UNIVERSITY
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