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Asymmetric cobaltocene cation derivative and preparation method thereof

A cobaltocene cation and asymmetric technology, applied in the field of asymmetric cobaltocene cation derivatives and their preparation, can solve the problem of less asymmetric cobaltene cation derivatives and the like

Inactive Publication Date: 2021-05-18
NORTHWESTERN POLYTECHNICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to limitations in synthesis, there are few reports on the synthesis of asymmetric cobaltocene derivatives.

Method used

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  • Asymmetric cobaltocene cation derivative and preparation method thereof
  • Asymmetric cobaltocene cation derivative and preparation method thereof
  • Asymmetric cobaltocene cation derivative and preparation method thereof

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preparation example Construction

[0049] The present invention provides the preparation method of the asymmetric cobaltocene cation derivative described in the above technical scheme, comprising the following steps:

[0050] when R is -C 7 H 9 COO(CH 2 ) 3 or R for and R' is -C 7 H 9 COOCH(CH 2 ) 2 or R for and R" is -C 7 H 9 COOCH 2 C(CH 2 ) 3 Time:

[0051] when X is PF 6 , the preparation method of the asymmetric cobaltocene cation derivative comprises the following steps:

[0052] The azido-alcohol compound, trimethylsilylethynyl cobaltocene hexafluorophosphate, catalyst, potassium carbonate and the first solvent are mixed, and a first click reaction is carried out to obtain a click product; the azido- The alcohol compound is 3-azido-1-propanol, 1,3-diazido-2-propanol or triazido-neopentanol;

[0053] Mixing the click product, 4-dimethylaminopyridine, norbornenecarbonyl chloride and the second solvent, and performing alcoholysis reaction to obtain an asymmetric cobaltocene cation derivat...

Embodiment 1

[0098]When R=-C 7 h 9 COO(CH 2 ) 3 Time:

[0099] Add 3-bromo-1-propanol (1.112g, 8mmol) into 10mL of anhydrous N,N-dimethylformamide (DMF), stir to dissolve, add sodium azide (1.56g, 24mmol), and After the reaction was completed and cooled to room temperature, DMF was distilled off under reduced pressure; 10 mL of dichloromethane and 10 mL of deionized water were added to the distilled mixture, and after the solid was completely dissolved, it was transferred to a separatory funnel, and 20 mL of Dichloromethane, extract and separate liquid, wash the organic phase three times with deionized water, then back-extract the aqueous phase with dichloromethane, combine the organic phases; add anhydrous sodium sulfate to the obtained organic phase, filter and wash the filter cake with dichloromethane To colorless, the filtrates were combined, the solvent was removed by rotary evaporation, and dried in vacuo to obtain 3-azido-1-propanol;

[0100] Take a 100mL round bottom flask, di...

Embodiment 2

[0106] When R=-C 5 h 4 C 5 h 5 FeCOO (CH 2 ) 3 Time:

[0107] Add 3-bromo-1-propanol (1.09g, 7.83mmol) and 4-dimethylaminopyridine (0.957g, 7.83mmol) into a 100mL round bottom flask, dissolve with 20mL of anhydrous dichloromethane, and Stir for 30min, then dissolve ferrocenecarbonyl chloride (1.08g, 4.35mmol) in 15mL of anhydrous dichloromethane and transfer it to a constant pressure dropping funnel, and slowly drop it into the above-mentioned round-bottomed flask under ice-bath conditions, After the reaction was over, add 50 mL of distilled water to quench the reaction, and extract the solution with dichloromethane, then back-extract the aqueous phase three times with dichloromethane; combine the organic phases, dry with anhydrous sodium sulfate, and rotary evaporate to obtain the crude product, column chromatography Purification to obtain ferrocenecarboxylic acid-3-bromo-1-propyl ester;

[0108] Add the ferrocenecarboxylic acid-3-bromo-1-propyl ester (0.98g, 2.79mmol)...

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Abstract

The invention provides an asymmetric cobaltocene cation derivative and a preparation method thereof, and belongs to the technical field of organometallic chemistry. The asymmetric cobaltocene cation derivative contains cobaltocene cations, so that the good stability of the cobaltocene cations under strong acidic and strong alkaline conditions can be exerted, and meanwhile, the cobaltocene cations also have counter ion dependence and oxidation-reduction properties, the derivative can be applied to the fields of self-assembly, antibacterial materials, metal corrosion inhibition and fuel cell diaphragms; meanwhile, norbornene capable of realizing ring-opening metathesis polymerization or a ferrocene group capable of realizing self-assembly through subject-object and electrochemical regulation is introduced into the cobaltocene asymmetric derivative, so that a good basis is provided for subsequent ring-opening metathesis polymerization and self-assembly research of the cobaltocene asymmetric derivative; the application of the cobaltocene derivative system can be enriched.

Description

technical field [0001] The invention relates to the technical field of organometallic chemistry, in particular to an asymmetric cobaltocene cation derivative and a preparation method thereof. Background technique [0002] Cobaltocene cations can show good stability under both strong acid and strong alkaline conditions. Meanwhile, the cobaltocene cations have novel and unique properties such as counter ion dependence and redox, which make cobaltocene derivatives suitable for smart Functional materials, environmentally friendly materials and biomedical materials have broad application prospects. However, due to synthetic limitations, there are few reports on the synthesis of asymmetric cobaltocene cationic derivatives. SUMMARY OF THE INVENTION [0003] The purpose of the present invention is to provide an asymmetric cobaltocene cation derivative and a preparation method thereof, wherein the cobaltene cation derivative introduces norbornene that can realize ring-opening meta...

Claims

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Application Information

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IPC IPC(8): C07F17/00
CPCC07F17/02
Inventor 闫毅徐鹏杨薇弘刘爽
Owner NORTHWESTERN POLYTECHNICAL UNIV
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