ADT type [ferric-ferric] hydrogenase model complex and synthesis method thereof

A synthesis method and technology of model substances, which are applied in the fields of iron organic compounds, chemical instruments and methods, organic compounds/hydrides/coordination complex catalysts, etc., can solve the problems of low synthesis efficiency and low catalytic hydrogen release performance, and achieve The effect of simple operation, simple synthesis method and high yield

Inactive Publication Date: 2019-02-15
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 problems of low synthesis efficiency and low catalytic hydrogen desorption performance of the existing ADT [iron-iron] hydrogenase act

Method used

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  • ADT type [ferric-ferric] hydrogenase model complex and synthesis method thereof
  • ADT type [ferric-ferric] hydrogenase model complex and synthesis method thereof
  • ADT type [ferric-ferric] hydrogenase model complex and synthesis method thereof

Examples

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Effect test

Embodiment 1

[0035] A method for synthesizing an ADT class [iron iron] hydrogenase active center model substance 1 containing a monophosphine ligand, the chemical formula of the model substance 1 being Fe 2 [(μ-SCH 2 ) 2 NH](CO) 5 [P(C 6 h 4 -4-CH 3 ) 3 ], its chemical synthesis process is as follows:

[0036]

[0037] Concrete synthetic steps are as follows:

[0038] Under the protection condition of inert 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 dark 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 15min Afterwards, add 0.16mL trifluoroacetic acid (2mmol), after continuing to react for 15min, add 304mg of P(C 6 h 4 -4-CH 3 ) 3 (1.0mmol), stirred at room temperature for 3h. Under the condition of inert gas protection, add 570 mg o...

Embodiment 2

[0043] A synthetic method of an ADT class [iron iron] hydrogenase active center model substance 2 containing a phosphine ligand, the chemical formula of the model substance 2 is Fe 2 [(μ-SCH 2 ) 2 NH](CO) 5 [PPh 2 (OCH 2 CH 3 )], its chemical synthesis process is as follows:

[0044]

[0045] Concrete synthetic steps are as follows:

[0046] Under the protection condition of inert gas, add 344mg Fe in the flask equipped with stirring magnet 2 S 2 (CO) 6 (1mmol) and 15-30mL of tetrahydrofuran solvent to obtain a deep red solution, the resulting solution was cooled to -78°C with a liquid nitrogen bath, and 2mL lithium triethylborohydride (1M in THF) solution was slowly added under stirring conditions, After reacting for 15min, add 0.18mL trifluoroacetic acid (2.2mmol), continue reacting for 15min, add 250mg of PPh 2 (OCH 2 CH 3 ) (1.1mmol), stirred at room temperature for 3h. Under inert gas protection conditions, add ground 570mg (NH 4 ) 2 CO 3 (6mmol) and 51...

Embodiment 3

[0050] A method for synthesizing an ADT class [iron iron] hydrogenase active center model substance 3 containing a monophosphine ligand, the chemical formula of the model substance 3 being Fe 2 [(μ-SCH 2 ) 2 NH](CO) 5 [P(2-C 4 h 3 O) 3 ], its chemical synthesis process is as follows:

[0051]

[0052] Concrete synthetic steps are as follows:

[0053] Under the protection condition of inert gas, add 344mg Fe in the flask equipped with stirring magnet 2 S 2 (CO) 6 (1mmol) and 15-30mL of tetrahydrofuran solvent to obtain a deep red solution, the resulting solution was cooled to -78°C with a liquid nitrogen bath, and 2mL lithium triethylborohydride (1M in THF) solution was slowly added under stirring conditions, After reacting for 15min, 0.18mL trifluoroacetic acid (2mmol) was added, and after continuing the reaction for 15min, 232mg of P(2-C 4 h 3 O) 3 (1mmol), stirred at room temperature for 3 h. Under the condition of inert gas protection, add 570 mg of finely g...

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Abstract

The invention provides an ADT type [ferric-ferric] hydrogenase model complex containing mono-phosphorus ligand, and belongs to the technical field of the synthesis. The model complex molecular formulais Fe2[(mu-SCH2)2NH](CO)5L, an the chemical structural formula is as shown in description, wherein L is mono-phosphorus ligand P(C6H4-4-CH3)3, PPh2(OCH2CH3), P(2-C4H3O)3, P(C6H4-3-CH3)3, and P(C6H4-4-F)3. The invention further provides a synthesis method of the ADT type [ferric-ferric] hydrogenase active center model complex containing the mono-phosphorus ligand. The synthesis method provided bythe invention adopts a one-pot synthesis method, the operation process is simple, the reaction condition is mild, the product yield is high, and the method can be suitable for the synthesis of multiple ADT type [ferric-ferric] hydrogenase active center model complex Fe2[(muon-SCH2)2NH](CO)5L containing the mono-phosphorus ligand. The hydrogenase active center model complex prepared by the invention has good catalytic hydrogen production capacity and potential industrial application value.

Description

technical field [0001] The invention belongs to the technical field of synthesis, in particular to an ADT-type [iron-iron] hydrogenase active center model substance Fe containing a monophosphine ligand 2 [(μ-SCH 2 ) 2 NH](CO) 5 L and its synthesis method. Background technique [0002] Since [iron-iron] hydrogenase has the ability to efficiently catalyze the reduction of protons to generate hydrogen in nature, and hydrogen is an efficient, pollution-free and clean energy source, the simulation of the active center structure of [iron-iron] hydrogenase has received extensive attention. This has also become a development frontier in the field of biometallic organic chemistry. In-depth study of its active center and catalytic mechanism can provide a simple way for a new type of cheap and efficient hydrogen production, and it also has important application prospects in solving new energy problems. [0003] Through research, it has been found that there are only a few cases of...

Claims

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Application Information

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IPC IPC(8): B01J31/24C07F15/02
CPCB01J31/24B01J31/2404B01J2531/842C07F15/02
Inventor 李玉龙赵培华何娇王正王铮母超李千利刘旭锋蒋金吴威平
Owner SICHUAN UNIVERSITY OF SCIENCE AND ENGINEERING
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