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Asymmetrically substituted iron-iron hydrogenase mimetic and its photochemical synthesis and application

A technology for photochemical synthesis and iron hydrogenase, which is applied in the fields of iron-organic compounds, chemical instruments and methods, organic compounds/hydrides/coordination complex catalysts, etc., to achieve the effects of moderate yield, single product, and easy preparation and operation.

Active Publication Date: 2019-08-16
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 solves the defects in the process of using the above two synthetic methods and more comprehensively chemically simulates three types of diiron disulfides containing different propene groups in natural iron-iron hydrogenase from the structure and function Catalytic active center, so this application adopts simple, mild and efficient general "photochemical synthesis method" to provide three types of amino bisphosphine chelating substituted iron-iron hydrogenase mimics containing different disulfide bridge groups, using electrochemical cyclic voltaic ANFA investigated their application in the electrocatalytic reduction of acetic acid protons to generate hydrogen

Method used

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  • Asymmetrically substituted iron-iron hydrogenase mimetic and its photochemical synthesis and application
  • Asymmetrically substituted iron-iron hydrogenase mimetic and its photochemical synthesis and application
  • Asymmetrically substituted iron-iron hydrogenase mimetic and its photochemical synthesis and application

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Experimental program
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Effect test

Embodiment 1

[0037] Photochemical synthesis of aminobisphosphine chelated substituted iron-iron hydrogenase mimic 1 containing azapropylene group, whose chemical formula is Fe 2 (μ-SCH 2 N(Ph)CH 2 S-μ)(CO) 4 {k 2 -(Ph 2 P) 2 N(CH 2 ) 3 NMe 2}, and its preparation process is as follows:

[0038]

[0039] Its concrete preparation steps are as follows:

[0040] 0.070g (0.15mmol) Fe 2 {μ-SCH 2 N(Ph)CH 2 S-μ}(CO) 6 and 0.085g (0.18mmol, 1.2 equivalents) (Ph 2 P) 2 N(CH 2 CH 2 CH 2 NMe 2 ) mixture was added to a long Schlenk bottle with a stirring magnet, and after the nitrogen was replaced 3 times, 90mL of toluene was injected and stirred to dissolve to obtain a light red solution; under the condition of avoiding light, the power was 20W and the wavelength was 365nm The above-mentioned mixed solution was irradiated vertically with a special LED lamp, and irradiated at room temperature for 2 hours. The red solution turned into a black-red solution. TLC monitored the disappe...

Embodiment 2

[0047] Photochemical synthesis of ethylene-containing aminobisphosphine chelated substituted iron-iron hydrogenase mimetic 2 with the chemical formula Fe 2 (μ-SCH 2 CH 2 S-μ)(CO) 4 {k 2 -(Ph 2 P) 2 N(CH 2 ) 3 NMe 2}, and its preparation process is as follows:

[0048]

[0049] Its concrete preparation steps are as follows:

[0050] 0.930g (0.25mmol) Fe 2 {μ-SCH 2 CH 2 S-μ}(CO) 6 and 0.142g (0.30mmol, 1.2 equivalents) (Ph 2 P) 2 N(CH 2 CH 2 CH 2 NMe 2 ) was added to a long-shaped Schlenk bottle with a stirring magnet, and after the nitrogen gas was replaced 3 times, 100 mL of toluene was injected and stirred to dissolve to obtain a light red solution; under the condition of avoiding light, the power was 20W and the wavelength was 365nm The above-mentioned mixed solution was irradiated vertically by a special LED lamp, and irradiated at room temperature for 3 hours. The red solution turned into a black-red solution. TLC monitored the disappearance of the re...

Embodiment 3

[0057] Photochemical synthesis of oxapropylene group-containing aminobisphosphine chelated substituted iron-iron hydrogenase mimic 3, whose chemical formula is Fe 2 (μ-SCH 2 OCH 2 S-μ)(CO) 4 {k 2 -(Ph 2 P) 2 N(CH 2 ) 3 NMe 2}, and its preparation process is as follows:

[0058]

[0059] Its concrete preparation steps are as follows:

[0060] 0.059g (0.15mmol) Fe 2 {μ-SCH 2 OCH 2 S-μ}(CO) 6 and 0.085g (0.18mmol, 1.2 equivalents) (Ph 2 P) 2 N(CH 2 CH 2 CH 2 NMe 2 ) mixture was added to a long Schlenk bottle with a stirring magnet, and after the nitrogen was replaced 3 times, 90mL of toluene was injected and stirred to dissolve to obtain a light red solution; under the condition of avoiding light, the power was 20W and the wavelength was 365nm The above-mentioned mixed solution was irradiated vertically with a special LED lamp, and irradiated at room temperature for 2 hours. The red solution turned into a black-red solution. TLC monitored that the reaction r...

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Abstract

The invention relates to the field of biological enzyme biomimetic chemistry and new energy materials, specifically to amido bisphosphine chelate-substituted Fe-Fe hydrogenase mimics, a photochemicalsynthesis method and application thereof. The mimics chemically simulate three kinds of basic structures containing different propylene-containing diiron disulfide butterfly-shaped skeletons of the natural Fe-Fe hydrogenase enzyme catalytic activity center and catalytic functions more comprehensively. Compared with the conventional oxidative decarbonylation method and heating reflux method, the photochemical synthesis method provided by the invention has the advantages of simple preparation and operation, mild reaction conditions, high reaction rate, single product and moderate yield. The photochemical synthesis method is suitable for preparation of various bidentate ligand asymmetrically substituted Fe-Fe hydrogenase mimics.

Description

technical field [0001] The invention relates to the fields of biological enzyme biomimetic chemistry and new energy materials, in particular to an amino bisphosphine chelating substituted iron-iron hydrogenase simulant containing different disulfide bridge groups and its photochemical synthesis method and catalytic application. Background technique [0002] Hydrogen is the best fuel for the next generation of clean and renewable energy. Existing hydrogen production technologies include chemical catalytic cracking, photo / electrochemical catalytic water splitting, etc. Among them, electrochemical technology has the advantages of high conversion efficiency and environmental protection, so it is widely used. At present, precious metal platinum is the best catalyst for industrial electrolysis of water to produce hydrogen. However, its price is expensive and resources are scarce. Therefore, it is the research field of new energy materials to find non-precious metal catalysts with ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/02B01J31/24C25B11/06C25B1/02
CPCB01J31/2409B01J35/0033B01J2531/0208B01J2531/0219B01J2531/842C07F15/025C25B1/02C25B11/075
Inventor 赵培华胡梦媛李建荣马钟义荆兴斌
Owner ZHONGBEI UNIV
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