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Double-substituted [iron-iron]-hydrogenase mimetic and its preparation method and application

A double-substitution and simulant technology is applied in the direction of iron-organic compounds, chemical instruments and methods, organic compounds/hydrides/coordination complex catalysts, etc. It can solve the problems of low hydrogen production capacity and achieve moderate product yields. The effect of simple and convenient operation and cheap and easy-to-obtain raw materials

Active Publication Date: 2019-08-23
ZHONGBEI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The present invention is aimed at the above technical analysis, and provides a chelated Double-substituted [iron-iron]-hydrogenase mimics or bridged P / N ligands and their preparation methods and applications

Method used

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  • Double-substituted [iron-iron]-hydrogenase mimetic and its preparation method and application
  • Double-substituted [iron-iron]-hydrogenase mimetic and its preparation method and application
  • Double-substituted [iron-iron]-hydrogenase mimetic and its preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0041] Preparation method of disubstituted [iron iron]-hydrogenase mimic 1 containing chelating P / N ligand, the chemical formula of which is Fe 2 (μ-SCH 2 CH 2 CH 2 S-μ)(CO) 4 {k 2 -Ph 2 PN(CH 2 CH 2 CH 2 Si(OEt) 3 )PPh 2 }, the preparation process is as follows:

[0042]

[0043] The specific preparation steps are as follows:

[0044] In a nitrogen atmosphere, 0.194g (0.50mmol) Fe 2 (μ-SCH 2 CH 2 CH 2 S-μ)(CO) 6 , 0.061g (0.55mmol) Me 3 NO·2H 2 O and 0.354g (0.60mmol) (Ph 2 P) 2 N(CH 2 CH 2 CH 2 Si(OEt) 3 Add the mixture of) to a Schlenk bottle with a stirring magnet, inject 20 mL of acetonitrile and stir to dissolve to obtain a red solution, react at room temperature for 0.5 h, the red solution turns into a black-red solution, stop the reaction, and remove the acetonitrile solvent by rotary evaporation and reduced pressure. The residue was extracted with dichloromethane, and the developing solvent was petroleum ether: ethyl acetate (v:v=10:1) for preparative thin-layer chromatogra...

Embodiment 2

[0047] Preparation method of double substituted [iron iron]-hydrogenase mimic 2 containing chelating P / N ligand, the chemical formula of which is Fe 2 (μ-SCH 2 CH 2 CH 2 S-μ)(CO) 4 {k 2 -Ph 2 PN(CH 2 CH 2 CH 2 NMe 2 )PPh 2 }, the preparation process is as follows:

[0048]

[0049] The specific preparation steps are as follows:

[0050] In a nitrogen atmosphere, 0.194g (0.50mmol) Fe 2 (μ-SCH 2 CH 2 CH 2 S-μ)(CO) 6 , 0.061g (0.55mmol) Me 3 NO·2H 2 O and 0.282g (0.60mmol) (Ph 2 P) 2 N(CH 2 CH 2 CH 2 NMe 2 Add the mixture of) into a Schlenk bottle with a stirring magnet, inject 20 mL of acetonitrile and stir to dissolve to obtain a red solution, react at room temperature for 1 hour, the red solution turns into a black-red solution, stop the reaction, and remove the acetonitrile solvent by rotary evaporation under reduced pressure. The residue was extracted with dichloromethane, and the eluent was dichloromethane: methanol (v:v=20:1) for silica gel flash chromatography, and the black-re...

Embodiment 3

[0053] Preparation method of double substituted [iron iron]-hydrogenase mimic 3 containing chelating P / N ligand, the chemical formula of which is Fe 2 (μ-SCH 2 CH 2 CH 2 S-μ)(CO) 4 {k 2 -Ph 2 PN(Bu n )PPh 2 }, the preparation process is as follows:

[0054]

[0055] The specific preparation steps are as follows:

[0056] In a nitrogen atmosphere, 0.194g (0.50mmol) Fe 2 (μ-SCH 2 CH 2 CH 2 S-μ)(CO) 6 , 0.061g (0.55mmol) Me 3 NO·2H 2 O and 0.266g (0.60mmol) (Ph 2 P) 2 NBu n Add the mixture to a Schlenk bottle with a stirring magnet, inject 20 mL of acetonitrile and stir to dissolve to obtain a red solution. React at room temperature for 15 minutes. The red solution turns into a black-red solution. Stop the reaction. The residue was extracted with methyl chloride, and the eluent was petroleum ether: dichloromethane (v:v=2:1) ​​for neutral alumina flash column chromatography to collect the red-brown main color band to obtain a red-brown solid. It is the target simulant 3 (0.250g, the yi...

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PUM

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Abstract

The invention relates to the field of biological enzyme biomimetic chemistry and novel energy materials, in particular to a disubstituted[iron iron]-hydrogenase stimulant comprising chelated or bridged P / N ligand as well as a preparation method and application thereof. The P / N ligand in the stimulant is coordinated at a same iron atom in a chelating manner or coordinated at two iron atoms in a bridging manner, and a chemical formula of the stimulant is Fe2(mu-SCH2CH2CH2S-mu)(CO)4{Ph2PN(R)PPh2}. Nitrogen atoms of the P / N ligand in the stimulant prepared by the invention can rapidly capture or transfer protons to efficiently generate hydrogen due to the alkalinity; and a series of novel disubstituted [iron iron]-hydrogenase stimulant comprising the chelated or bridged P / N ligand has potential excellent catalytic hydrogen generation capacity.

Description

Technical field [0001] The invention relates to the fields of bioenzyme biomimetic chemistry and new energy materials, in particular to a double-substituted [iron-iron]-hydrogenase mimic containing chelating or bridging P / N ligands, and a preparation method and application thereof. Background technique [0002] At present, natural [iron-iron]-hydrogenase is a type of metalloenzyme found in nature that can catalytically reduce protons to hydrogen with the highest catalytic efficiency. Although hydrogen is a clean new energy material with the advantages of high combustion heat, renewability, and no pollution after combustion, today's industrialized hydrogen production is mainly realized by electrolyzing water with high-cost, high-energy precious metal platinum catalysts. Based on this, many scientific researchers are actively trying to prepare a class of biomimetic enzyme catalysts based on cheap metals and efficient hydrogen production through in-depth research on natural [iron ir...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/02B01J31/22C01B3/02
Inventor 赵培华荆兴斌胡梦媛李玉龙马钟义
Owner ZHONGBEI UNIV
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