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Preparation method of electrochemiluminescent material based on zinc porphyrin

A technology of electrochemistry and luminescent materials, applied in luminescent materials, chemical instruments and methods, organic chemistry, etc., can solve the problems of poor water solubility, poor biocompatibility, and unsuitable biological applications, and achieve high water solubility and biocompatibility The effect of high stability and stable ECL signal

Inactive Publication Date: 2017-07-25
NANJING UNIV OF SCI & TECH
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  • Abstract
  • Description
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Problems solved by technology

[0004] Aiming at the shortcomings of existing porphyrin-based electrochemiluminescent materials, such as poor water solubility, unstable luminescence, poor biocompatibility, and unsuitability for biological applications, the present invention provides an electrochemiluminescent material based on zinc porphyrin The preparation method, the method forms a dimer through β-cyclodextrin and 3,5-dichloromethylpyridine, and then coordinates with zinc porphyrin to form a host-guest package through axial coordination, and prepares a light-emitting stable, high-intensity High, biocompatible, water-soluble ECL luminescent material

Method used

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  • Preparation method of electrochemiluminescent material based on zinc porphyrin
  • Preparation method of electrochemiluminescent material based on zinc porphyrin
  • Preparation method of electrochemiluminescent material based on zinc porphyrin

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Experimental program
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Effect test

Embodiment 1

[0024] ECL signal detection of zinc porphyrins.

[0025] 1. The meta-tetraphenylsulfonic acid base zinc porphyrin (a), 2,4-diethylene glycol hypo zinc porphyrin (b), hypo zinc porphyrin (c) and meta-tetrakis (N- Methyl-4-pyridyl) zinc porphyrin (d) and meta-tetrapyridine zinc porphyrin (e) were uniformly prepared into a 0.5 mM aqueous solution, and ultrasonicated at room temperature for 30 min.

[0026] 2. Polish the glassy carbon electrode with a diameter of 5mm on the chamois leather of 0.3μm and 0.05μm alumina respectively for 3 minutes, rinse the alumina adsorbed on the surface of the electrode with ultrapure water each time, and then wash it with acetone, ethanol, deionized Ultrasonic in water, dry with nitrogen gas for later use.

[0027] 3. Add 15 μL of different porphyrin solutions dropwise to the surface of the treated glassy carbon electrode, and dry it in a thermostat at 37° C. for 1 hour to obtain a working electrode.

[0028] 4. With pH 7.4 HEPES solution as the...

Embodiment 2

[0031] The synthesis of seven-(2,6-methoxy)-β-cyclodextrin dimer, the synthetic route is as follows image 3 As shown, the specific steps are:

[0032] 1. Weigh 5g of hepta-(2,6-methoxy)β-cyclodextrin (DMe-β-CD) and dissolve it in 80mL of anhydrous tetrahydrofuran to form a white translucent solution, continue stirring, then slowly add 1g containing 60 % sodium hydride in mineral oil (the mass ratio of DMe-β-CD is 5:1), and the mixture was refluxed for 1 h.

[0033] 2. Weigh 0.2g of 3,5-dichloromethylpyridine (the molar ratio of DMe-β-CD is 1:2) and dissolve it in 20mL of dry N,N-dimethylformamide, and use a constant pressure funnel Add it dropwise to the above reaction system over 1 hour, continue to stir the reaction, and reflux overnight.

[0034] 3. After the reaction was completed, methanol was slowly added under ice-bath conditions until the mixture became transparent, and distillation under reduced pressure was carried out. The residue obtained was dissolved in 40 mL ...

Embodiment 3

[0039] The synthesis of seven-(2,6-methoxy)-β-cyclodextrin dimer, the synthetic route is as follows image 3 As shown, the specific steps are:

[0040] 1. Weigh 5 g of seven-(2,6-methoxy) β-cyclodextrin (DMe-β-CD) and dissolve it in 80 mL of anhydrous tetrahydrofuran to form a white translucent solution, continue stirring, and then slowly add 0.5 g containing 60% sodium hydride in mineral oil (3:1 with DMe-β-CD), the mixture was refluxed for 1h.

[0041] 2. Weigh 0.09g of 3,5-dichloromethylpyridine (the ratio of DMe-β-CD is 1:5) and dissolve it in 20mL of dry N,N-dimethylformamide (DMF), and use constant The pressure funnel was added dropwise to the above reaction system over 1 hour, and the stirring reaction was continued, and the mixture was refluxed overnight.

[0042] 3. After the above reaction was completed, methanol was slowly added under ice-bath conditions until the mixture became transparent, and distillation under reduced pressure was carried out. The resulting re...

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Abstract

The invention discloses a preparation method of an electrochemiluminescent material based on zinc porphyrin. The electrochemiluminescent material is synthesized through chemical modification by using beta-cyclodextrin and m-tetraphenylsulfonic zinc porphyrin. The preparation method comprises the steps: first, using sodium hydride to restore 7-(2,6- methoxyl) beta-cyclodextrin, adding 3,5-dichloromethyl pyridine to conduct a substitution reaction to form beta-cyclodextrin dimer, adding the m-tetraphenylsulfonic zinc porphyrin, and using a manner of axial coordination to form the electrochemiluminescent material. The electrochemiluminescent material prepared by the invention is high in biocompatibility, stable in ECL signal, high in water solubility, close to an actual detection system, and capable of being applied to efficient and sensitive analysis and detection.

Description

technical field [0001] The invention belongs to the field of biotechnology, and relates to a preparation method of an electrochemiluminescence material based on zinc porphyrin. Background technique [0002] Visualized ECL technology has shown significant advantages in the field of image signal transduction. Traditional ECL luminophores mainly include ruthenium bipyridyl and its derivatives or complexes which depend on the positive potential response. Although many organic dyes, polycyclic aromatic hydrocarbons, heterocyclic compounds, and ionic liquid crystals, including the boron-dipyrromethene (BODIPY) series, have shown their outstanding potential in ECL color development or electrochromism, However, there are problems such as poor water solubility, instability of reaction transition state and free radical intermediate, and narrow potential window of working electrode in aqueous solution (Sheehan, S.W. et al. A Molecular Catalyst for Water Oxidation that Binds to Metal O...

Claims

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Application Information

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IPC IPC(8): C07D487/22C09K11/06
CPCC07D487/22C09K11/06C09K2211/188
Inventor 邓盛元郑晨昱马科锋杨阳崔宏达
Owner NANJING UNIV OF SCI & TECH
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