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Fe-Fe hydrogenase model compound containing oxa-trimethylene ditelluride bridge and preparation method of model compound

A technology of iron hydrogenase and model substance, which is applied in the fields of iron organic compounds, chemical instruments and methods, organic compounds/hydrides/coordination complex catalysts, etc. problem, to achieve the effect of convenient post-processing, high yield and mild reaction conditions

Inactive Publication Date: 2017-05-10
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, so far, there have been few studies on hydrogenase model substances containing diiron-ditellurium butterfly-like skeletons, mainly because tellurium has strong metallicity compared to its congeners sulfur and selenium, but its coordination ability with metals is weak.
Therefore, it is very difficult to synthesize such model substances containing tellurium atoms, especially the iron-iron hydrogenase model substances containing oxapropylene ditellurium bridges have not been reported in the literature so far.

Method used

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  • Fe-Fe hydrogenase model compound containing oxa-trimethylene ditelluride bridge and preparation method of model compound
  • Fe-Fe hydrogenase model compound containing oxa-trimethylene ditelluride bridge and preparation method of model compound
  • Fe-Fe hydrogenase model compound containing oxa-trimethylene ditelluride bridge and preparation method of model compound

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Embodiment 1

[0018] A method for preparing an iron-iron hydrogenase model substance 1 containing an oxapropylene ditellurium bridge, the chemical formula of the model substance 1 is [(μ-TeCH 2 ) 2 O]Fe 2 (CO) 6 , the preparation process is as follows:

[0019]

[0020] Concrete preparation steps are as follows:

[0021] 1) Under nitrogen protection, add 30mL tetrahydrofuran into a 100mL round-bottomed Schlenk flask equipped with a stirring magnet, cool to -78°C with a liquid nitrogen-acetone bath, and add 0.5mmol (μ-Te) 2 Fe 2 (CO) 6 Petroleum ether solution (20mL) was added in the reaction flask and stirred evenly;

[0022] 2) Add 1mL LiEt to the above system 3 BH (1mol / L in THF), naturally warming up to room temperature;

[0023] 3) Add 90 μL of dichlorodimethyl ether, raise the temperature to 60°C, and react for 12 hours;

[0024] 4) The solvent was removed under reduced pressure, and the product was separated by thin-layer chromatography, using dichloromethane / petroleum eth...

Embodiment 2

[0027] A method for preparing an iron-iron hydrogenase model substance 2 containing an oxapropylene ditellurium bridge, the chemical formula of the model substance 2 is [(μ-TeCH2 ) 2 O]Fe 2 (CO) 5 (L 1 )[L 1 =1,3-bis(2,4,6-trimethylphenyl)imidazole-2-carbene], the preparation process is as follows:

[0028]

[0029] Concrete preparation steps are as follows:

[0030] 1) Under nitrogen protection, add 269mg (0.79mmol) 1,3-bis(2,4,6-trimethylphenyl)imidazole hydrochloride and 20mL tetrahydrofuran to a 100mL round-bottomed Schlenk flask equipped with a stirring magnet ;

[0031] 2) Add 155 mg (1.38 mmol) potassium tert-butoxide to the above suspension and stir evenly. After reacting at room temperature for 2 hours, the reaction solution changes from white turbidity to yellow clarification;

[0032] 3) Add 94 mg (0.16 mmol) of the model substance to it, and react for 2 hours at room temperature;

[0033] 4) filter with a sand core funnel filled with silica gel and wash s...

Embodiment 3

[0036] A method for preparing an iron-iron hydrogenase model substance 3 containing an oxapropylene ditellurium bridge, the chemical formula of the model substance 3 is [(μ-TeCH 2 ) 2 O]Fe 2 (CO) 5 (L 2 )[L 2 =1-2,4,6-trimethylphenyl-3-methylimidazole-2-carbene], the preparation process is as follows:

[0037]

[0038] Concrete preparation steps are as follows:

[0039] 1) Under nitrogen protection, add 262mg (0.8mmol) 1-2,4,6-trimethylphenyl-3-methylimidazole iodide and 15mL tetrahydrofuran into a 50mL round-bottomed Schlenk flask equipped with a stirring magnet;

[0040] 2) Add 1 mL (1.6 mmol) of n-butyllithium in n-hexane dropwise to the above suspension, and the reaction solution turns from white turbidity to yellow clarification;

[0041] 3) Add 58 mg (0.1 mmol) of the model substance to it, and react at room temperature for 1.5 h;

[0042] 4) filter with a sand core funnel filled with silica gel and wash several times with dichloromethane to remove inorganic sa...

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PUM

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Abstract

The invention discloses a Fe-Fe hydrogenase model compound containing an oxa-trimethylene ditelluride bridge. The chemical structural formula is shown in the specification, wherein L is carbonyl, 1,3-bis(2,4,6-trimethylphenyl) imidazole-2-carbene, 1,2,4,6-trimethylphenyl-3-methylimidazole-2-carbene or 1,3-dimethylimidazole-2-carbene. The invention has the beneficial effects that the Fe-Fe hydrogenase model compound containing the oxa-trimethylene ditelluride bridge is prepared by utilizing the method, the method is mild in reaction conditions, convenient in after-treatment, high in yield and suitable for preparation of multiple Fe-Fe hydrogenase model compounds containing the oxa-trimethylene ditelluride bridge, and the model compounds have excellent potential catalytic hydrogen production capacity.

Description

technical field [0001] The invention belongs to the field of metal organic, energy and material sciences, in particular to an iron-iron hydrogenase model substance containing an oxapropylene ditellurium bridge and a preparation method thereof. Background technique [0002] Hydrogenase is a class of metal-containing biological enzymes that exist in a variety of microorganisms, and has the ability to reversibly catalyze the conversion of protons into hydrogen under mild conditions. Due to the high-efficiency catalytic hydrogen production performance of this kind of biological enzymes and its great theoretical significance and potential application value in bio-enzyme biomimetic chemistry and material science, it has attracted widespread attention of scientific researchers. According to the structure and function of the active center of hydrogenase, hydrogenase can be divided into three categories: iron-iron hydrogenase, nickel-iron hydrogenase and iron hydrogenase. Among them,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/02B01J31/22C01B3/02
CPCB01J31/2213B01J31/2273B01J2531/0241B01J2531/842C01B3/02C07F15/02
Inventor 宋礼成江烽贾国君陈锦森
Owner NANKAI UNIV
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