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Oxa-trimethylene (FeFe) hydrogenase active center model compound containing monophosphine ligand and synthesizing method thereof

A technology of hydrogenase activity and synthesis method is applied in the field of oxiliene [iron iron] hydrogenase active center model substances and the synthesis field thereof, which can solve the problems of low catalytic hydrogen release performance and the like, and achieves simple, easy to operate, mild conditions

Active Publication Date: 2017-05-17
SICHUAN UNIVERSITY OF SCIENCE AND ENGINEERING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The object of the present invention is to: aim at the problem that the existing [iron-iron] hydrogenase active center model substance has lower catalytic hydrogen desorption performance, provide a kind of oxapropylene class (ODT) class [iron-iron] containing monophosphine ligand ] Hydrogenase active center model and its synthesis method, the model has a good electron-donating phosphine ligand in the structure, can improve catalytic activity and has potential industrial application value

Method used

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  • Oxa-trimethylene (FeFe) hydrogenase active center model compound containing monophosphine ligand and synthesizing method thereof
  • Oxa-trimethylene (FeFe) hydrogenase active center model compound containing monophosphine ligand and synthesizing method thereof
  • Oxa-trimethylene (FeFe) hydrogenase active center model compound containing monophosphine ligand and synthesizing method thereof

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Embodiment 1

[0034] A kind of synthetic method of oxirane (ODT) type [iron iron] hydrogenase active center model object 1 containing monophosphine ligand, the chemical formula of described model object 1 is Fe 2 [(SCH 2 ) 2 O](CO) 5 [P(C 6 h 4 -4-CH 3 ) 3 ], its chemical synthesis process is as follows:

[0035]

[0036] Concrete synthetic steps are as follows:

[0037] Under nitrogen protection conditions, add 344mg Fe 2 S 2 (CO) 6 (1mmol) and 15mL of tetrahydrofuran solvent to obtain a deep red solution, the resulting solution was cooled to -75°C with a liquid nitrogen bath, and 2mL of lithium triethylborohydride (1Min THF) solution was slowly added under stirring conditions, and after 15min of reaction , add 0.18mL trifluoroacetic acid (2mmol), continue to react after 15min, add 0.2mL formaldehyde solution (37%wt), the reaction system is raised to room temperature, after stirring for 2h, add 304mg of P(C 6 h 4 -4-CH 3 ) 3 (1mmol), after stirring at room temperature for ...

Embodiment 2

[0042] A kind of synthetic method of oxirane (ODT) class [iron iron] hydrogenase active center model object 2 containing monophosphine ligand, the chemical formula of described model object 2 is Fe 2 [(SCH 2 ) 2 O](CO) 5 [P(C 6 h 4 -4-F) 3 ], its chemical synthesis process is as follows:

[0043]

[0044] Concrete synthetic steps are as follows:

[0045] Under the protection condition of argon gas, add 344mg Fe in the flask equipped with stirring magnet 2 S 2 (CO) 6 (1mmol) and 15mL of tetrahydrofuran solvent to obtain a deep red solution, the resulting solution was cooled to -78°C with a liquid nitrogen bath, and 2mL of lithium triethylborohydride (1M in THF) solution was slowly added under stirring conditions, and reacted for 10min Afterwards, 0.18 mL of trifluoroacetic acid was added, and after continuing the reaction for 15 min, 0.18 mL of formaldehyde solution (37% wt) was added, the reaction system was raised to room temperature, and 320 mg of P(C 6 h 4 -4-...

Embodiment 3

[0050] A method for synthesizing an oxapropylene class [iron iron] hydrogenase active center model substance 3 containing a monophosphine ligand, the chemical formula of the model substance 3 being Fe 2 [(SCH 2 ) 2 O](CO) 5 (Ph 2 PCH 2 CH 3 ), and its chemical synthesis process is as follows:

[0051]

[0052] Concrete synthetic steps are as follows:

[0053] Under the condition of nitrogen gas protection, add 344mg Fe in the flask equipped with stirring magnet 2 S 2 (CO) 6 (1mmol) and 20mL of tetrahydrofuran solvent to obtain a deep red solution, the resulting solution was cooled to -80°C with a liquid nitrogen bath, and 2.2mL of lithium triethylborohydride (1M in THF) solution was slowly added under stirring conditions, and the reaction After 15 minutes, add 0.2 mL of trifluoroacetic acid, continue the reaction for 10 minutes, add 0.2 mL of formaldehyde solution (37% wt), raise the reaction system to room temperature, stir for 2 hours, then add 235 mg of Ph 2 PC...

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Abstract

The invention provides an oxa-trimethylene (FeFe) hydrogenase active center model compound containing monophosphine ligand and belongs to the technical field of synthesis. The center model compound is Fe2((SCH2)2O)(CO)5(PR3), and a chemical structural formula of the center model ompound is shown in the description, wherein the PR3 is P(C6H4-4-CH3)3, P(C6H4-4-F)3, and Ph2PCH2CH3. The invention further provides a synthesizing method of the oxa-trimethylene (FeFe) hydrogenase active center model ompound containing the monophosphine ligand. The synthesizing method of the invention has the advantages of having simple operation process and moderate reaction condition and being suitable for synthesizing varieties of oxa-trimethylene (FeFe) hydrogenase active center model ompounds containing the monophosphine ligand. The oxa-trimethylene (FeFe) hydrogenase active center model ompound, containing monophosphine ligand, prepared through the synthesizing method has advantages of good electro-catalysis hydrogen generation capacity and potential industrial application value.

Description

technical field [0001] The invention belongs to the technical field of synthesis, in particular to an oxapropylene type [iron-iron] hydrogenase active center model substance containing a monophosphine ligand and a synthesis method thereof. Background technique [0002] In order to maintain the rapid growth of my country's economy and solve the problems of energy shortage and greenhouse effect that are common in the world, the country clearly proposes to further promote the energy revolution, focus on promoting the transformation of energy production and utilization methods, optimize the energy structure, improve energy utilization efficiency, and build A clean, low-carbon, safe and efficient modern energy system. Compared with other chemical fuels, hydrogen has a higher combustion calorific value, and the product of combustion is only water, which will not cause any pollution to the environment. It is regarded as the clean energy with the most development potential in the 21s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/02B01J31/24
CPCC07F15/02B01J31/24B01J35/39
Inventor 李玉龙邹立科母超邓成龙吴宇赵培华谢斌罗强
Owner SICHUAN UNIVERSITY OF SCIENCE AND ENGINEERING
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