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A model substance of iron-iron hydrogenase containing [2p2n]cu(i) photosensitizer and its preparation method

A technology of iron-iron hydrogenase and model substance, which is applied in the fields of metal organic and energy sciences, and achieves the effects of mild reaction conditions, high yield, and cheap and easy-to-obtain raw materials

Inactive Publication Date: 2017-11-03
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, a light-driven iron-iron hydrogenase model containing [2P2N]Cu(I) photosensitizer has not been synthesized yet.

Method used

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  • A model substance of iron-iron hydrogenase containing [2p2n]cu(i) photosensitizer and its preparation method
  • A model substance of iron-iron hydrogenase containing [2p2n]cu(i) photosensitizer and its preparation method
  • A model substance of iron-iron hydrogenase containing [2p2n]cu(i) photosensitizer and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] A preparation method containing [2P2N]Cu(I) photosensitizer iron-iron hydrogenase model substance 1, the chemical formula of the model substance is [Fe 2 (PDT)(CO) 5 CNC 6 h 4 -C≡C(bpy)Cu(I)dppp] (1), wherein dppp is 1,3-bis(diphenylphosphine)propane, and the specific preparation steps are as follows:

[0024] Firstly, the [2N] ligand containing the [2Fe2S] catalytic center needs to be prepared. The preparation process and structural reaction formula are as follows:

[0025]

[0026] 1) Under the protection of high-purity argon, add 117 mg (0.2 mmol) of compound A, 40 mg (0.2 mmol) of 5-ethynyl-2,2' - bipyridine, 25mg (catalytic amount) Pd (PPh 3 ) 4 and 8 mg (catalytic amount) of CuI.

[0027] 2) Subsequent gas replacement is performed on the system at room temperature to replace the oxygen in the system with argon as much as possible. Subsequently, 20 mL of tetrahydrofuran / triethylamine mixed system (v / v=5:1) was added as the reaction solvent, and the reacti...

Embodiment 2

[0036] A preparation method of an iron-iron hydrogenase model substance 2 containing [2P2N]Cu(I) photosensitizer, the chemical formula of the model substance is [Fe 2 (PDT)(CO) 5 CNC 6 h 4 C≡C(bpy)Cu(I)dppv](2), wherein dppv is cis-1,2-bis(diphenylphosphine)ethylene, the preparation process and reaction formula are as follows:

[0037]

[0038] The specific preparation steps are basically the same as in Example 2, except that the bisphosphine ligand added in step 4) was changed to 20 mg (0.05 mmol) cis-1,2-bis(diphenylphosphine)ethylene (dppv), 54mg of orange-red solid product was obtained, yield 91%. The product structure data is characterized as follows: IR(KBr disk):ν N≡C :2123(vs);ν C≡O :2039(vs),1996(vs),1970(s)cm -1 . 1 H NMR (400MHz, CDCl 3 ):1.83-2.18(m,6H),7.07-8.72(m,33H)ppm. 13 C NMR (100MHz, CDCl 3 ):23.5(s),30.5(s),87.1(s),94.1(s),122.0-151.7(m),171.6(s),209.4(s),210.8(s)ppm. 31 P NMR (161.9MHz, CDCl 3 ):-2.32(s)ppm. 19 F NMR (376MHz, CDCl 3 ):-15...

Embodiment 3

[0040] A preparation method of an iron-iron hydrogenase model substance 3 containing [2P2N]Cu(I) photosensitizer, the chemical formula of the model substance is [Fe 2 (PDT)(CO) 5 CNC 6 h 4 C≡C(bpy)Cu(I)POP] (3), wherein POP is two (2-bisphenylphosphophenyl) ethers, and the preparation process and reaction formula are as follows:

[0041]

[0042] The specific preparation steps are basically the same as in Example 2, except that the bisphosphine ligand added in step 4) is changed to 27mg (0.05mmol) bis(2-bisphenylphosphophenyl) ether (POP) to obtain 60mg Orange-red solid, yield 90%.

[0043] The product structure data is characterized as follows: IR(KBr disk):ν N≡C :2122(vs);ν C≡O :2040(vs),1998(vs),1970(vs)cm -1 . 1 H NMR (400MHz, CDCl 3 ):1.81-2.17(m,6H),6.78-8.57(m,39H)ppm. 13 CNMR (100MHz, CDCl 3 ):23.5(s),30.5(s),87.3(s),93.8(s),120.4-158.2(m),171.5(s),209.5(s),210.8(s)ppm. 31 P NMR (161.9MHz, CDCl 3 ):-10.92(s)ppm. 19 F NMR (376MHz, CDCl 3 ):-153.4(s)ppm....

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Abstract

A model substance of iron-iron hydrogenase containing [2P2N]Cu(I) photosensitizer, which contains [2Fe2S] catalytic center and [2P2N]Cu(I) photosensitizer, both of which are passed through an isocyanide and bipyridine ligand linked by conjugated bridges. This type of model substance has a chemical structural formula as shown below: the bisphosphine ligand in the structural formula includes 1,3-bis(diphenylphosphine) propane (dppp); cis-1,2-bis(diphenylphosphine)ethylene (dppv); bis(2‑diphenylphosphophenyl) ether (POP); 1,1'‑bis(diphenylphosphine)ferrocene (dppf); 1,2‑bis(diphenylphosphine) Benzene (dppb). The beneficial effects of the present invention are: the preparation process is simple, the raw materials are cheap and easy to obtain, the reaction conditions are mild, and the yield is high; various iron-iron hydrogenases containing [2P2N]Cu(I) photosensitizers can be prepared by changing the bisphosphine ligand model objects.

Description

technical field [0001] The invention belongs to the field of organometallic and energy sciences, in particular to an iron-iron hydrogenase model substance containing a [2P2N]Cu(I) photosensitizer and a preparation method thereof Background technique [0002] In the context of increasingly prominent contemporary energy and environmental problems, it has become an important task that people are eager to solve to find a renewable green energy as a fuel to replace fossil fuels such as oil and coal that have limited resources and can cause serious environmental pollution. Iron-iron hydrogenase is a metalloenzyme that exists in microorganisms and can efficiently catalyze the reduction of protons to hydrogen. In recent years, people have conducted extensive and in-depth research on it and its biomimetic chemistry, trying to synthesize a cheap and efficient "artificial enzyme" catalyst by simulating its active center structure, so that it can catalyze water in water under the action...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F19/00B01J31/24
Inventor 宋礼成谷振超牛政邢续康
Owner NANKAI UNIV
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