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[ferronickel]hydrogenase model compound containing dppf skeleton and O-alkyldithiophosphate ligand and preparation method thereof

A technology of alkyl dithiophosphoric acid and hydrogenase, which is applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, chemical/physical processes, etc., to achieve simple preparation methods, convenient post-processing, and reaction The effect of mild conditions

Inactive Publication Date: 2017-11-17
SICHUAN UNIVERSITY OF SCIENCE AND ENGINEERING
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the [nickel-iron] hydrogenase model substance containing dppf backbone and O-alkyl dithiophosphate ligand has not been reported yet

Method used

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  • [ferronickel]hydrogenase model compound containing dppf skeleton and O-alkyldithiophosphate ligand and preparation method thereof
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  • [ferronickel]hydrogenase model compound containing dppf skeleton and O-alkyldithiophosphate ligand and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] A [nickel-iron] hydrogenase model substance containing a dppf skeleton and an O-alkyl dithiophosphate ligand, which is composed of a dppf structural unit and an O-alkyl dithiophosphate ligand connected to a metal nickel atom A double metal complex, the chemical formula of the [nickel-iron] hydrogenase model substance is (dppf)Ni(S 2 P{O}OCH 3 ), its chemical structure is as follows:

[0025]

[0026] A method for preparing the [nickel-iron] hydrogenase model substance containing dppf skeleton and O-alkyl dithiophosphate ligand, the steps are as follows:

[0027] 1) In a round-bottomed flask equipped with a magnetic stir bar, 0.231g (CH 3 O) 2 P.S. 2 NH 2 Et 2 (1mmol), 0.342g (dppf) NiCl 2 (0.5mmol) and 25mL of methanol were mixed, stirred and reacted at 25°C for 3 hours to obtain a red solution;

[0028] 2) Rotary evaporator removes the solvent under reduced pressure, dissolves with 3ml of dichloromethane, and then uses a mixed solvent of dichloromethane and ...

Embodiment 2

[0031] The chemical formula of the [nickel-iron] hydrogenase model substance containing dppf skeleton and O-alkyl dithiophosphate ligand is (dppf)Ni(S 2 P{O}OCH 2 CH 3 ), its chemical structure is as follows:

[0032]

[0033] A method for preparing the [nickel-iron] hydrogenase model substance containing dppf skeleton and O-alkyl dithiophosphate ligand, the steps are as follows:

[0034] 1) In a round-bottomed flask equipped with a magnetic stir bar, 0.259g (CH 3 CH 2 O) 2 P.S. 2 NH 2 Et 2 (1mmol), 0.342g (dppf) NiCl 2(0.5mmol) and 25mL of chloroform were mixed, stirred and reacted at 60°C for 5 hours to obtain a red solution;

[0035] 2) Rotary evaporator removes the solvent under reduced pressure, dissolves it with 3ml of dichloromethane, and then uses a mixed solvent of dichloromethane and tetrahydrofuran with a volume ratio of 10:1 as a developing solvent for thin-layer chromatography separation, collects the red band, and after elution Obtained 0.322g, yield...

Embodiment 3

[0038] The chemical formula of the [nickel-iron] hydrogenase model substance containing dppf skeleton and O-alkyl dithiophosphate ligand is (dppf)Ni(S 2 P{O}OCH 2 Ph), its chemical structure is as follows:

[0039]

[0040] A method for preparing the [nickel-iron] hydrogenase model substance containing a dppf skeleton and an O-alkyl dithiophosphate ligand, the steps are basically the same as in Example 2, the difference is that in step 1), the raw material O, O'-diethyldithiophosphoric acid-N,N-diethylammonium was changed to 0.383g (PhCH 2 O) 2 P.S. 2 NH 2 Et 2 (1 mmol), the developer is a mixed solvent of dichloromethane and tetrahydrofuran with a volume ratio of 8:1, and 0.350 g of a red product is obtained with a yield of 84.2%.

[0041] Product characterization data are as follows: IR (KBr, cm -1 ): 1038m(P-O-(C)), 1001m((P)-O-C), 694s, 575m(PS 2 ), 635w, 546m, 515m, 494s, 462m (Fe-Cp). 1 H NMR (400.0MHz, CDCl 3 ):4.259(s,4H,Fc),4.412(s,4H,Fc),4.952(d,J=8.4H...

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Abstract

The invention provides a [ferronickel]hydrogenase model compound containing dppf skeleton and O-alkyldithiophosphate ligand. The [ferronickel]hydrogenase model compound is a bimetallic complex formed by connection of 1, 1'-bis(diphenylphosphine)ferrocene (dppf) structural unit and the O-alkyldithiophosphate ligand with metal nickel atom, and has a chemical structure shown as the specification, wherein R can be methyl, ethyl, benzyl or phenethyl. The synthesis method provided by the invention has the advantages of simple operation, mild reaction conditions, simple post-treatment and high yield, etc., is suitable for synthesis of a variety of [ferronickel]hydrogenase model compounds containing 1, 1'-bis(dialkylphosphine)ferrocene skeleton and O-alkyldithiophosphate ligand, and the model compounds have good catalytic hydrogen production performance, thus having potential industrial application value.

Description

technical field [0001] The invention relates to the fields of metal organic chemistry and hydrogen energy development, in particular to a [nickel-iron] hydrogenase model substance containing a dppf skeleton and an O-alkyl dithiophosphoric acid ligand and a preparation method thereof. Background technique [0002] Energy is the driving force of social and economic development. After the industrial revolution, the development and application of fossil energy by human beings has driven the rapid development of science and technology and economy. The development of modern society is increasingly dependent on the development and utilization of energy. However, the use of fossil energy has caused environmental pollution. For example, the carbon dioxide produced has exacerbated the greenhouse effect, and other toxic and harmful substances have affected human health. In addition, the reserves of fossil energy are limited. Therefore, the development and utilization of new energy has...

Claims

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Application Information

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IPC IPC(8): C07F17/02B01J31/22C01B3/02
CPCC07F17/02B01J31/2409B01J2531/0225B01J2531/0238B01J2531/842C01B3/02
Inventor 谢斌马枭魏健赖川邓成龙邹立科李玉龙吴宇冯建申
Owner SICHUAN UNIVERSITY OF SCIENCE AND ENGINEERING
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