CN110343137B - Trinuclear ruthenium complex and preparation method and application thereof - Google Patents
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- 239000012327 Ruthenium complex Substances 0.000 title claims abstract description 78
- 238000002360 preparation method Methods 0.000 title abstract description 10
- 239000013078 crystal Substances 0.000 claims abstract description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 claims description 22
- 239000000243 solution Substances 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
- 230000005855 radiation Effects 0.000 claims description 14
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cis-cyclohexene Natural products C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 11
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 claims description 11
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 150000003303 ruthenium Chemical class 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002889 diamagnetic material Substances 0.000 claims description 5
- 230000001476 alcoholic effect Effects 0.000 claims description 4
- 239000002178 crystalline material Substances 0.000 claims description 3
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims 1
- YAYGSLOSTXKUBW-UHFFFAOYSA-N ruthenium(2+) Chemical class [Ru+2] YAYGSLOSTXKUBW-UHFFFAOYSA-N 0.000 claims 1
- -1 triphenylruthenium (0) unit Chemical group 0.000 abstract description 7
- 230000005292 diamagnetic effect Effects 0.000 abstract description 4
- 230000005298 paramagnetic effect Effects 0.000 abstract description 4
- YEAYAPUZMIAOIY-UHFFFAOYSA-N ClC1=C(C(=C(C=C1)[Ru+2])Cl)Cl Chemical group ClC1=C(C(=C(C=C1)[Ru+2])Cl)Cl YEAYAPUZMIAOIY-UHFFFAOYSA-N 0.000 abstract description 3
- ZMSMGZKFZAFITD-UHFFFAOYSA-N c1ccc(cc1)[Ru](c1ccccc1)c1ccccc1 Chemical compound c1ccc(cc1)[Ru](c1ccccc1)c1ccccc1 ZMSMGZKFZAFITD-UHFFFAOYSA-N 0.000 abstract description 3
- 230000005496 eutectics Effects 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- 230000005291 magnetic effect Effects 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000010586 diagram Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000013110 organic ligand Substances 0.000 description 5
- GZPPANJXLZUWHT-UHFFFAOYSA-N 1h-naphtho[2,1-e]benzimidazole Chemical class C1=CC2=CC=CC=C2C2=C1C(N=CN1)=C1C=C2 GZPPANJXLZUWHT-UHFFFAOYSA-N 0.000 description 4
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 229910052707 ruthenium Inorganic materials 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000005034 decoration Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000005389 magnetism Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0046—Ruthenium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
- C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic Table
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01F—MAGNETS; INDUCTANCES; TRANSFORMERS; SELECTION OF MATERIALS FOR THEIR MAGNETIC PROPERTIES
- H01F1/00—Magnets or magnetic bodies characterised by the magnetic materials therefor; Selection of materials for their magnetic properties
- H01F1/0018—Diamagnetic or paramagnetic materials, i.e. materials with low susceptibility and no hysteresis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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Abstract
The invention provides a trinuclear ruthenium complex and a preparation method and application thereof, belonging to the field of crystal materials. The trinuclear ruthenium complex provided by the invention has a structure shown in formula I, the complex is formed into a eutectic by combining a triphenylruthenium (0) unit and two trichloro-monophenyl ruthenium (III) units, the molecule is a P-1 point group, and the triphenylruthenium (0) unit in the molecule is D6hThe point group and the molecular overall structure are highly symmetrical systems taking triphenyl ruthenium as a symmetrical center, and the trinuclear ruthenium complex provided by the invention is paramagnetic under the low-field condition and diamagnetic under the high-field condition.
Description
Technical Field
The invention relates to the field of crystal materials, in particular to a trinuclear ruthenium complex and a preparation method and application thereof.
Background
The ruthenium complex has wide application in the fields of biomedicine, materials, photosensitizers, catalysis and the like. The arene ruthenium compound is a complex obtained by forming a coordination bond between an aromatic benzene ring or pi electrons on a substituted arene benzene ring and ruthenium. However, to date, there have been no reports in the prior art relating to trinuclear ruthenium complexes.
Disclosure of Invention
The trinuclear ruthenium complex provided by the invention has better magnetism and better application prospect in diamagnetic materials.
The invention provides a trinuclear ruthenium complex which has a structure shown in a formula I:
preferably, the trinuclear ruthenium complex is a crystalline material, and the crystal size of the trinuclear ruthenium complex is 0.18mm × 0.16mm × 0.14 mm.
Preferably, the trinuclear ruthenium complex has unit cell parameters of:
α＝95.530°，β＝112.366°，γ＝93.826°。
preferably, the space group of the trinuclear ruthenium complex is P-1.
The invention also provides a preparation method of the trinuclear ruthenium complex, which comprises the following steps:
mixing ruthenium trichloride, 1, 3-cyclohexadiene and an alcohol solution, and performing microwave radiation to obtain a trinuclear ruthenium complex; the temperature of the microwave radiation is 60-150 ℃.
Preferably, the molar ratio of the ruthenium trichloride to the 1, 3-cyclohexadiene is 1: 1-4.
Preferably, the alcohol solution comprises an aqueous methanol solution or an aqueous ethanol solution; the volume ratio of methanol to water in the methanol aqueous solution is 9: 1-1: 9; the volume ratio of ethanol to water in the ethanol water solution is 9: 1-1: 9.
Preferably, the dosage ratio of the ruthenium trichloride to the alcoholic solution is 6.3mmol (5-20 mL).
The invention also provides application of the trinuclear ruthenium complex in the technical scheme as a diamagnetic material.
The invention also provides the application of the trinuclear ruthenium complex in the technical scheme in the preparation of the ruthenium complex.
The trinuclear ruthenium complex provided by the invention has a structure shown in a formula I, one triphenylruthenium (0) unit and two trichloro-monophenyl ruthenium (III) units are combined to form a eutectic, the molecule is P1 point group, and the triphenylruthenium (0) unit in the molecule is D6hThe dot group and the molecular overall structure are highly stacked systems taking triphenyl ruthenium as a symmetric center, so that the trinuclear ruthenium complex provided by the invention is paramagnetic under a low-field condition and diamagnetic under a high-field condition. The results of the examples show that the trinuclear ruthenium complex provided by the invention is prepared under the low-field condition (<700Oe), the magnitude of the magnetic moment increases with increasing strength of the magnetic field, under high field conditions (c) ((m)>700Oe) the magnetic moment decreases with increasing magnetic field strength.
Drawings
FIG. 1 is a diagram of the coordination environment of the trinuclear ruthenium complex prepared in example 1;
FIG. 2 is a space-stacking diagram of the trinuclear ruthenium complex prepared in example 1;
FIG. 3 is a space-stacking diagram of the trinuclear ruthenium complex prepared in example 1;
FIG. 4 is a space-stacking diagram of the trinuclear ruthenium complex prepared in example 1;
FIG. 5 is a graph showing the change in magnetic properties of the trinuclear ruthenium complex prepared in example 1 depending on the intensity of magnetic field.
Detailed Description
The invention provides a trinuclear ruthenium complex which has a structure shown in a formula I:
the trinuclear ruthenium complex provided by the invention is preferably a crystalline material, and the crystal size of the trinuclear ruthenium complex is preferably 0.18mm multiplied by 0.16mm multiplied by 0.14 mm.
In the present invention, the unit cell parameters of the trinuclear ruthenium complex are preferably:
95.530 ° α, 112.366 ° β, 93.826 ° γ; the space group of the trinuclear ruthenium complex is preferably P-1.
The complex provided by the invention is formed by combining a triphenylruthenium (0) unit and two trichloro-monophenyl ruthenium (III) units to form a eutectic, the molecule is a P-1 space group, and the triphenylruthenium (0) unit in the molecule is D6hThe dot group and the molecular overall structure are highly stacked systems taking triphenyl ruthenium as a symmetric center, so that the trinuclear ruthenium complex provided by the invention is paramagnetic under a low-field condition and diamagnetic under a high-field condition.
The invention also provides a preparation method of the trinuclear ruthenium complex, which comprises the following steps:
mixing ruthenium chloride, 1, 3-cyclohexadiene and an alcohol solution, and performing microwave radiation to obtain a trinuclear ruthenium complex; the microwave heating temperature is 60-150 ℃.
In the invention, the preparation process of the trinuclear ruthenium complex is shown as formula II:
the invention mixes ruthenium chloride, 1, 3-cyclohexadiene and alcohol solution. In the invention, the molar ratio of the ruthenium trichloride to the 1, 3-cyclohexadiene is preferably 1: 1-4, and more preferably 1: 2-3. In the present invention, the alcohol solution preferably includes an aqueous methanol solution or an aqueous ethanol solution; the volume ratio of methanol to water in the methanol aqueous solution is preferably 9: 1-1: 9, more preferably 8: 1-1: 8, and even more preferably 5: 1-1: 5; the volume ratio of the ethanol to the water in the ethanol aqueous solution is preferably 9: 1-1: 9, more preferably 8: 1-1: 8, and even more preferably 5: 1-1: 5. In the invention, the dosage ratio of the ruthenium trichloride to the alcoholic solution is preferably 6.3mmol: 5-20 mL, and more preferably 6.3mmol: 10-15 mL. The mixing mode of the ruthenium trichloride, the 1, 3-cyclohexadiene and the alcoholic solution is not particularly required in the invention, and the mixing mode known by the technicians in the field can be adopted.
After the mixing is finished, the obtained mixture is subjected to microwave radiation to obtain the trinuclear ruthenium complex. In the invention, the temperature of the microwave radiation is preferably 60-150 ℃, and more preferably 80-120 ℃; the time of the microwave radiation is preferably 5s to 60min, more preferably 1min to 50min, and even more preferably 5 to 30 min. The invention preferably controls the temperature and time of microwave radiation within the range, which is beneficial to the full reaction between reaction raw materials to prepare the trinuclear ruthenium complex.
The invention also provides application of the trinuclear ruthenium complex in the technical scheme as a diamagnetic material. The trinuclear ruthenium complex provided by the invention is paramagnetic under the condition of a low field and diamagnetic under the condition of a high field, so that the trinuclear ruthenium complex provided by the invention can be applied as a diamagnetic material.
The invention also provides the application of the trinuclear ruthenium complex in the technical scheme in the preparation of the ruthenium complex. In the present invention, the use of the trinuclear ruthenium complex for preparing a ruthenium complex preferably includes: the trinuclear ruthenium complex disclosed by the invention is coordinated with other organic ligands to generate a new ruthenium complex, so that the application range of the ruthenium complex is expanded. In the present invention, the organic ligand preferably comprises an organic ligand of the structure shown in formula III or formula IV:
in the present invention, the reaction scheme of the trinuclear ruthenium complex and the organic ligand having the structure shown in formula III is preferably shown in formula V:
in the present invention, the reaction scheme of the trinuclear ruthenium complex and the organic ligand having the structure shown in formula IV is preferably shown in formula VI:
in the present invention, in formula V and formula VI [ (eta)6-C6H6)2Ru]·2[(η6-C6H6)Cl3Ru]Represents the trinuclear ruthenium complex in the technical scheme.
The technical solution of the present invention will be clearly and completely described below with reference to the embodiments of the present invention.
Example 1
1, 3-cyclohexadiene (6.3mmol) and RuCl were added to a microwave reaction tube3·3H2O (1.65g, 6.3mmol) and 20mL of ethanol aqueous solution with 90 percent (V: V) volume fraction react for 10min at the microwave radiation temperature of 60 ℃ to obtain the trinuclear ruthenium complex with the yield of 65 percent; and a large amount of hydrogen is generated.
Example 2
1, 3-cyclohexadiene (25.2mmol) and RuCl were added to a microwave reaction tube3·3H2O(1.65g，6.3mmol)，20mL of methanol aqueous solution with volume fraction of 90% (V: V) reacts for 15min at the microwave radiation temperature of 100 ℃ to obtain the trinuclear ruthenium complex with the yield of 73%; and a large amount of hydrogen is generated.
Example 3
1, 3-cyclohexadiene (18.9mmol) and RuCl were added to a microwave reaction tube3·3H2O (1.65g, 6.3mmol) and 20mL of methanol aqueous solution with 90 percent (V: V) volume fraction react for 5min at the microwave radiation temperature of 150 ℃ to obtain the trinuclear ruthenium complex with the yield of 90 percent; and a large amount of hydrogen is generated.
Example 4
Adding the trinuclear ruthenium complex (68.8mg, 0.1mmol) synthesized in example 1, a phenanthroimidazole derivative ligand PIP ((88.8mg,0.3mmol) and 20mL of dichloromethane solution into a microwave reaction tube, and reacting at the microwave radiation temperature of 70 ℃ for 10min to obtain a mononuclear ruthenium complex with the yield of 95%;
the structural formula of the phenanthroimidazole derivative ligand PIP is as follows:
the structural formula of the mononuclear ruthenium complex prepared in example 4 is:
example 5
Adding the trinuclear ruthenium complex (68.8mg, 0.1mmol) synthesized in example 1, phenanthroimidazole derivative ligand p-FPIP (94.2mg,0.3mmol) and 20mL of dichloromethane solution into a microwave reaction tube, and reacting at the microwave radiation temperature of 70 ℃ for 10min to obtain the mononuclear ruthenium complex with the yield of 87%;
the structural formula of the phenanthroimidazole derivative ligand p-FPIP is as follows:
the structural formula of the mononuclear ruthenium complex prepared in example 5 is:
the coordination environment of the trinuclear ruthenium complex prepared in example 1 is shown in fig. 1, and it can be seen from fig. 1 that the trinuclear ruthenium complex prepared in the present invention has the structure shown in formula I, and the crystallinity of the trinuclear ruthenium complex synthesized in the present invention is better as can be seen from the sphericity of atoms in fig. 1. In FIG. 1, the green sphere is chlorine atom, the gray sphere is carbon atom, the blue sphere is nitrogen atom, the red sphere is oxygen atom, and the light gray sphere is hydrogen atom.
The trinuclear ruthenium complex prepared in example 1 was subjected to a single crystal structure test, and the crystal parameters of the trinuclear ruthenium complex are shown in table 1:
TABLE 1 Crystal Structure parameters of trinuclear ruthenium complexes
The bond length data for the trinuclear ruthenium complexes prepared in example 1 are shown in Table 2:
TABLE 2 bond length data for trinuclear ruthenium complexes
The bond angle data for the trinuclear ruthenium complexes prepared in example 1 are shown in Table 3:
TABLE 3 bond Angle data for trinuclear ruthenium complexes
The spatial stacking structure of the trinuclear ruthenium complex prepared in example 1 is shown in fig. 2, 3 and 4, in which fig. 2 is a spatial stacking structure diagram in the a direction, fig. 3 is a spatial stacking structure diagram in the b direction, and fig. 4 is a spatial stacking structure diagram in the c direction. In fig. 2 to 4, the green sphere is a chlorine atom, the gray sphere is a carbon atom, the blue sphere is a nitrogen atom, the red sphere is an oxygen atom, and the light gray sphere is a hydrogen atom.
The trinuclear ruthenium complex prepared in example 1 was subjected to a magnetic test, and the results are shown in FIG. 5. As can be seen from fig. 5, in the low field condition (<700Oe), the magnetic moment of the trinuclear ruthenium complex provided by the present invention increases with the strength of the magnetic field, and in the high field condition (>700Oe), the magnetic moment decreases with the strength of the magnetic field.
The crystal structure parameters and magnetism of the trinuclear ruthenium complex prepared in the embodiments 2-3 are tested, and the test results are similar to those of the embodiment 1 and are not repeated herein.
From the embodiment 4 and the embodiment 5, the trinuclear ruthenium complex provided by the invention can be used for other preparation of ruthenium complexes, has high yield, and effectively expands the application range of ruthenium complexes.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (7)
1. A trinuclear ruthenium complex having the structure of formula I:
2. the trinuclear ruthenium complex according to claim 1, which is a crystalline material and has a crystal size of 0.18mm by 0.16mm by 0.14 mm.
3. The trinuclear ruthenium complex according to claim 1, wherein the trinuclear ruthenium complex has unit cell parameters of:
α＝95.530°，β＝112.366°，γ＝93.826°。
4. the trinuclear ruthenium complex according to claim 1, wherein the space group of the trinuclear ruthenium complex is P-1.
5. A process for preparing the trinuclear ruthenium complex according to any one of claims 1 to 4, comprising the steps of:
mixing ruthenium trichloride, 1, 3-cyclohexadiene and an alcohol solution, and then carrying out microwave radiation to obtain a trinuclear ruthenium complex; the temperature of the microwave radiation is 80-150 ℃;
the molar ratio of the ruthenium trichloride to the 1, 3-cyclohexadiene is 1: 1-4;
the alcohol solution is methanol water solution or ethanol water solution; the volume ratio of methanol to water in the methanol aqueous solution is 9: 1-1: 9; the volume ratio of ethanol to water in the ethanol water solution is 9: 1-1: 9;
the dosage ratio of the ruthenium trichloride to the alcoholic solution is 6.3mmol (5-20 mL).
6. Use of the trinuclear ruthenium complex according to any one of claims 1 to 4 as a diamagnetic material.
7. Use of the trinuclear ruthenium complexes according to any of claims 1 to 4 for preparing ruthenium (II) complexes.
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| KR20030002015A (en) * | 2001-06-30 | 2003-01-08 | 한국화학연구원 | Process for preparing ruthenium complex coordinated with a ligand containing benzene and 1, 3-cyclohexadiene |
| CN102898479A (en) * | 2012-09-13 | 2013-01-30 | 广东药学院 | Microwave-assisted synthesis method for dual-core ruthenium (II) arene compound |
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| KR20030002015A (en) * | 2001-06-30 | 2003-01-08 | 한국화학연구원 | Process for preparing ruthenium complex coordinated with a ligand containing benzene and 1, 3-cyclohexadiene |
| CN102898479A (en) * | 2012-09-13 | 2013-01-30 | 广东药学院 | Microwave-assisted synthesis method for dual-core ruthenium (II) arene compound |
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| Title |
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| Electrochemistry of organometallic halide complexes III*. Oxidation of [ C6Me6RuCl2]2;Ulrich KOlle et al.;《Inorganica Chlmica Acta》;20010417;33-39页 * |
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