CN109705168B - Binuclear nickel coordination compound and preparation method and application thereof - Google Patents
Binuclear nickel coordination compound and preparation method and application thereof Download PDFInfo
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- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 title claims abstract description 66
- 150000001875 compounds Chemical class 0.000 title claims abstract description 28
- 229910052759 nickel Inorganic materials 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 60
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000013078 crystal Substances 0.000 claims abstract description 17
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims abstract description 16
- NBPGPQJFYXNFKN-UHFFFAOYSA-N 4-methyl-2-(4-methylpyridin-2-yl)pyridine Chemical group CC1=CC=NC(C=2N=CC=C(C)C=2)=C1 NBPGPQJFYXNFKN-UHFFFAOYSA-N 0.000 claims abstract description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000002244 precipitate Substances 0.000 claims abstract description 14
- 239000011259 mixed solution Substances 0.000 claims abstract description 13
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 12
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 10
- 239000000460 chlorine Substances 0.000 claims abstract description 10
- 239000011941 photocatalyst Substances 0.000 claims abstract description 10
- MJFCDPLEATUOPF-UHFFFAOYSA-L dichloronickel;triphenylphosphane Chemical compound Cl[Ni]Cl.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 MJFCDPLEATUOPF-UHFFFAOYSA-L 0.000 claims abstract description 8
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 5
- 239000007789 gas Substances 0.000 claims abstract description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 10
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 8
- 229910052786 argon Inorganic materials 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 239000003446 ligand Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910001453 nickel ion Inorganic materials 0.000 abstract description 5
- 239000000047 product Substances 0.000 abstract description 5
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical group [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 abstract description 4
- 230000001699 photocatalysis Effects 0.000 abstract description 3
- 239000000243 solution Substances 0.000 abstract description 2
- 238000001704 evaporation Methods 0.000 abstract 1
- 239000005431 greenhouse gas Substances 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 230000009467 reduction Effects 0.000 description 5
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- 238000012937 correction Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 241000239290 Araneae Species 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 238000002447 crystallographic data Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000002803 fossil fuel Substances 0.000 description 2
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- 239000013110 organic ligand Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000282414 Homo sapiens Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- -1 chlorine ions Chemical class 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000002484 cyclic voltammetry Methods 0.000 description 1
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- 229910002804 graphite Inorganic materials 0.000 description 1
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- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910000765 intermetallic Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- ZBRJXVVKPBZPAN-UHFFFAOYSA-L nickel(2+);triphenylphosphane;dichloride Chemical compound [Cl-].[Cl-].[Ni+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 ZBRJXVVKPBZPAN-UHFFFAOYSA-L 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
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Abstract
本发明公开了一种双核镍配位化合物及其制备方法与应用。配位化合物为[(dmbpy)2Ni2Cl4(H2O)2]，分子结构式为C24H28Cl4N4Ni2O2，其中dmbpy为4,4'‑二甲基‑2,2'‑联吡啶，Ni为二价镍离子，形态为固态晶体。该配位化合物的晶体属于三斜晶系，P‑1空间群。4,4'‑二甲基‑2,2'‑联吡啶与镍离子通过氯桥键形成双核分子结构。制备方法为：将二氯化三苯基膦镍[NiCl2(PPh3)2]与4,4'‑二甲基‑2,2'‑联吡啶在乙腈溶液中反应得到绿色沉淀，然后把沉淀溶解在乙腈和乙醇的混合溶液中，通过缓慢挥发溶剂得到绿色晶体。本发明可作为一种光催化剂，把温室气体二氧化碳转变为具有高附加值的甲烷气体和CO。本发明制备工艺简单，易实施，产物纯度和产率均较高，在二氧化碳的光催化转化领域具有良好的应用前景。
The invention discloses a dual-nuclear nickel coordination compound and a preparation method and application thereof. The coordination compound is [(dmbpy) 2 Ni 2 Cl 4 (H 2 O) 2 ], the molecular structural formula is C 24 H 28 Cl 4 N 4 Ni 2 O 2 , wherein dmbpy is 4,4'-dimethyl-2 ,2'-bipyridine, Ni is a divalent nickel ion, and the form is a solid crystal. The crystal of the coordination compound belongs to the triclinic system, P-1 space group. 4,4'-dimethyl-2,2'-bipyridine and nickel ions form a binuclear molecular structure through chlorine bridge bonds. The preparation method is as follows: reacting triphenylphosphine nickel dichloride [NiCl 2 (PPh 3 ) 2 ] with 4,4'-dimethyl-2,2'-bipyridine in an acetonitrile solution to obtain a green precipitate, and then adding The precipitate was dissolved in a mixed solution of acetonitrile and ethanol, and green crystals were obtained by slowly evaporating the solvent. The invention can be used as a photocatalyst to convert the greenhouse gas carbon dioxide into methane gas and CO with high added value. The preparation process of the invention is simple, easy to implement, high in product purity and yield, and has good application prospects in the field of photocatalytic conversion of carbon dioxide.
Description
Technical Field
The invention relates to the technical field of coordination compound materials, in particular to a binuclear metal coordination compound and a preparation method and application thereof, and more particularly relates to a binuclear nickel coordination compound and a preparation method and application thereof.
Background
At present, most of energy used by human beings comes from fossil fuels, such as petroleum, coal and the like. Release of large amounts of CO due to combustion of fossil fuels2It poses a serious challenge to the global environmental problem. Introducing CO2The idea of reduction to a chemical fuel with high added value is one of the effective methods for solving this problem. To achieve this, the CO can be catalytically reduced using visible light2And new fuels such as CO, methane and the like are obtained. The efficient photocatalyst is sought to solve CO2The key to the reduction is. The traditional photocatalyst generally adopts noble metal compounds, such as Ru, Ir, Pt and Pd complexes. Due to high price and harsh synthesis conditions, the compound is not easy to realize large-scale industrial production. However, reports on the reduction of carbon dioxide by using cheap metallic nickel as a photocatalyst are rare, and particularly reports on the conversion of the cheap metallic compound into methane by using carbon dioxide are extremely rare. The compound is selected as the photocatalyst, has the great advantage of low cost and has extremely high potential value.
Disclosure of Invention
In view of this, the object of the invention is to use 4,4 '-dimethyl-2, 2' -bipyridine ligand and triphenylphosphine nickel dichloride [ NiCl ]2(PPh3)2]The binuclear nickel coordination compound is used as a catalyst and applied to the reduction of photocatalytic carbon dioxide to obtain methane gas and CO with high added values.
In order to solve the technical problems, the invention adopts the following technical scheme:
(I) providing a photocatalyst material
The catalyst material was [ (dmbpy)2Ni2Cl4(H2O)2]Wherein dmbpy represents an organic ligand 4,4 '-dimethyl-2, 2' -bipyridine, Ni is divalent nickel ion, the nickel ion of the catalyst material and the organic ligand 4,4 '-dimethyl-2, 2' -bipyridine form a binuclear nickel coordination compound through a chlorine bridge bond, and the structural formula is as follows.
(II) method for preparing dinuclear nickel coordination compound
The preparation method comprises the following steps:
s1, mixing 4,4 '-dimethyl-2, 2' -bipyridyl and [ NiCl ]2(PPh3)2]Mixing evenly in acetonitrile solution;
s2, introducing argon into the mixed liquid obtained in the step S1, and reacting for 6-24 hours under stirring. After the reaction is finished, green precipitate is obtained;
and S3, dissolving the green precipitate obtained in the step S2 by using a mixed solution of acetonitrile and ethanol, and slowly volatilizing to obtain a green needle crystal.
Further, in the step S1, 4 '-dimethyl-2, 2' -bipyridine and [ NiCl2(PPh3)2]The molar ratio of (A) to (B) is 1:0.5 to 1: 1.
Further, the reaction temperature in the step S2 is 50 to 80 ℃.
Further, the volume ratio of acetonitrile in the mixed solution of the step S3 is 20-80%.
Application of (tri) binuclear nickel coordination compound
The binuclear nickel coordination compound is used as a catalyst and applied to the photocatalytic reduction of carbon dioxide to convert the carbon dioxide into methane gas and CO.
Compared with the prior art, the invention has the following beneficial effects:
firstly, the characteristic of the multi-coordination site of 4,4 '-dimethyl-2, 2' -bipyridine is utilized to achieve the purpose of forming a coordination compound with nickel ions. The chlorine bridge bond is led to obtain the coordination structure of binuclear nickel.
The binuclear nickel coordination compound has a plurality of chloride ions and water molecules coordinated with the nickel ions, and has the characteristic of easy removal in catalytic ligand substitution.
Secondly, the nickel coordination compound is adopted, and the characteristic that the metal nickel is cheap and easy to obtain is utilized.
Thirdly, the photocatalyst material of the invention has simple preparation, good reproducibility, high yield and high product purity.
Fourthly, the photocatalyst of the invention has stable structure and high thermal stability.
Drawings
FIG. 1 is a molecular structure diagram of a binuclear nickel complex.
FIG. 2 is a graph showing simulated powder diffraction contrast of a single crystal sample and a single crystal of binuclear nickel complex. The figure demonstrates that the single crystal sample synthesized is consistent with the diffraction peak of the simulated powder diffraction, indicating that the synthesized sample is high in purity and is the target product.
FIG. 3 is a schematic diagram showing the coordination structure of a binuclear nickel complex. The figure shows that nickel ions form a binuclear coordination compound through a chlorine bridge bond, two water molecules participate in coordination, and the coordination of the chlorine ions and the water molecules provides a catalytic reaction site for a catalytic process.
FIG. 4 is a cyclic voltammogram of a binuclear nickel complex. The figure shows that the synthesized binuclear nickel coordination compound has large oxidation-reduction potential and shows high catalytic activity.
FIG. 5 is a gas chromatographic detection of a product using a binuclear nickel complex as a photocatalyst. The figure shows that when using binuclear nickel complex as a catalyst, it is possible to reduce carbon dioxide to methane and carbon monoxide.
FIG. 6 is a mass spectrum of the product obtained by isotope tracing. Isotope tracking experiments show that methane and carbon monoxide come from the added carbon dioxide sample, further proving the effectiveness of the catalyst.
Detailed Description
The present invention will be described in further detail with reference to specific examples.
(I) preparation of binuclear nickel coordination compound material
Example 1
36.65mg (0.2mmol) of 4,4 '-dimethyl-2, 2' -bipyridine and 131.24mg (0.2mmol) of triphenylphosphine nickel dichloride are added into 50mL of acetonitrile and mixed uniformly; introducing argon into the obtained mixed solution, and stirring and reacting at 50 ℃ for 20 hours to obtain green precipitate; the precipitate was dissolved with a mixed solution of acetonitrile and ethanol, wherein the volume of acetonitrile was 50%. Slowly volatilizing for 2 weeks to obtain a green single crystal sample.
Example 2
36.65mg (0.2mmol) of 4,4 '-dimethyl-2, 2' -bipyridine and 65.62mg (0.1mmol) of triphenylphosphine nickel dichloride are added to 40mL of acetonitrile and mixed uniformly; introducing argon into the obtained mixed solution, and stirring and reacting for 15 hours at the temperature of 60 ℃ to obtain green precipitate; the precipitate was dissolved with a mixed solution of acetonitrile and ethanol, wherein the volume of acetonitrile was 50%. Slowly volatilizing for 2 weeks to obtain a green single crystal sample.
Example 3
36.65mg (0.2mmol) of 4,4 '-dimethyl-2, 2' -bipyridine and 98.28mg (0.15mmol) of triphenylphosphine nickel dichloride are added into 60mL of acetonitrile and mixed uniformly; introducing argon into the obtained mixed solution, and stirring and reacting for 15 hours at 70 ℃ to obtain green precipitate; the precipitate was dissolved with a mixed solution of acetonitrile and ethanol, wherein the volume of acetonitrile was 60%. Slowly volatilizing for 2 weeks to obtain a green single crystal sample.
Example 4
36.65mg (0.2mmol) of 4,4 '-dimethyl-2, 2' -bipyridine and 65.62mg (0.1mmol) of triphenylphosphine nickel dichloride are added to 40mL of acetonitrile and mixed uniformly; introducing argon into the obtained mixed solution, and stirring and reacting for 10 hours at 70 ℃ to obtain green precipitate; the precipitate was dissolved with a mixed solution of acetonitrile and ethanol, wherein the volume of acetonitrile was 70%. Slowly volatilizing for 2 weeks to obtain a green single crystal sample.
Determination of Structure of (Di) binuclear Nickel Complex
Table 1: parameter table of binuclear nickel coordination compound crystal
Selecting single crystal with proper size under microscope, and monochromating with graphite monochromator on Rigaku R-AXIS SPIDER diffractometer at T293 (2) K
To be provided with
The diffraction data is collected. Absorption correction was performed by the ABSCOR program. The structure was resolved and refined using the SHELXTL program using the direct method. Firstly, determining all non-hydrogen atom coordinates by a difference function method and a least square method, carrying out full matrix least square method correction on the non-hydrogen atom coordinates and anisotropic parameters, then obtaining the hydrogen atom position of a main body framework by a theoretical hydrogenation method, and then carrying out fine correction on the crystal structure by the least square method. Some of the parameters for crystallographic diffraction point data collection and structure refinement are shown in table 1 above.
Powder diffraction data collection was done on a Rigaku D-MAX 2200VPC diffractometer.
Single crystal diffraction was performed on a Rigaku R-AXIS SPIDER diffractometer.
Gas chromatography detection was done in SHIMADZU GC-2014C.
It should be understood that the above-described embodiments of the present invention are merely examples for clearly illustrating the present invention, and are not intended to limit the embodiments of the present invention. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. Any modification, equivalent replacement, and improvement made within the spirit and principle of the present invention should be included in the protection scope of the claims of the present invention.
Claims (7)
1. A binuclear nickel complex characterized in that said complex has the chemical formula of [ (dmbpy)2Ni2Cl4(H2O)2]Wherein dmbpy is 4,4 '-dimethyl-2, 2' -bipyridine, and the coordination compound forms a binuclear nickel coordination structure through a chlorine bridge bond; the structural formula of the coordination compound is
2. The binuclear nickel complex compound according to claim 1, wherein the crystals of said complex compound belong to the triclinic system, the space group is P-1, and the unit cell parameters are:a = 6.8592(9) Å、b = 10.1220(10)Å、c = 10.8673(10) Å，V = 657.32(13) Å3。
3. a process for preparing the binuclear nickel complex compound of claim 1 comprising the steps of:
s1 preparation of 4,4 '-dimethyl-2, 2' -bipyridine and triphenylphosphine nickel dichloride [ NiCl ]2(PPh3)2]Mixing evenly in acetonitrile;
s2, introducing argon into the mixed liquid obtained in the step S1, and reacting for 6-24 hours under stirring to obtain green precipitates;
s3, dissolving the green precipitate obtained in the step S2 in a mixed solution of acetonitrile and ethanol, and slowly volatilizing to obtain green needle crystals.
4. The method of claim 3, wherein the 4,4 '-dimethyl-2, 2' -bipyridine ligand and triphenylphosphine nickel dichloride [ NiCl ] in the step S12(PPh3)2]The molar ratio of (A) to (B) is 1:0.5 to 1: 1.
5. The preparation method of claim 3, wherein the reaction temperature of the step S2 is 50-80 ℃.
6. The preparation method according to claim 3, wherein the volume ratio of acetonitrile in the mixed solution of step S3 is 20-80%.
7. The dinuclear nickel complex compound according to claim 1 as a photocatalyst for converting carbon dioxide into methane gas and CO.
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| CN110787838B (en) * | 2019-10-09 | 2021-10-29 | 江苏医药职业学院 | A kind of binuclear complex and its preparation method and application |
| CN110818744A (en) * | 2019-11-04 | 2020-02-21 | 中国科学院昆明植物研究所 | A kind of mononuclear nickel coordination compound and its preparation method and application |
| CN112341501B (en) * | 2020-11-12 | 2023-06-20 | 云南师范大学 | A tetranuclear nickel-based complex with tetramethylphenanthroline as a ligand, its synthesis method and photocatalytic application |
| JP7291165B2 (en) * | 2021-02-25 | 2023-06-14 | 株式会社豊田中央研究所 | Carbon dioxide reduction catalyst, carbon dioxide reducer, and artificial photosynthesis device |
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