CN111039964A - Tetrahedral cage-like structure complex and preparation method thereof - Google Patents
Tetrahedral cage-like structure complex and preparation method thereof Download PDFInfo
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- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 238000010668 complexation reaction Methods 0.000 title description 2
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000001338 self-assembly Methods 0.000 claims abstract description 7
- JDYVLWWFVYNMTN-UHFFFAOYSA-N 3-methylpyridine-2-carbaldehyde Chemical compound CC1=CC=CN=C1C=O JDYVLWWFVYNMTN-UHFFFAOYSA-N 0.000 claims abstract description 5
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims abstract description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims abstract description 4
- ZMLPZCGHASSGEA-UHFFFAOYSA-M zinc trifluoromethanesulfonate Chemical compound [Zn+2].[O-]S(=O)(=O)C(F)(F)F ZMLPZCGHASSGEA-UHFFFAOYSA-M 0.000 claims abstract description 4
- CITILBVTAYEWKR-UHFFFAOYSA-L zinc trifluoromethanesulfonate Substances [Zn+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F CITILBVTAYEWKR-UHFFFAOYSA-L 0.000 claims abstract description 4
- 150000002466 imines Chemical class 0.000 claims abstract 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- 239000007810 chemical reaction solvent Substances 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- WEVYAHXRMPXWCK-FIBGUPNXSA-N acetonitrile-d3 Chemical compound [2H]C([2H])([2H])C#N WEVYAHXRMPXWCK-FIBGUPNXSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000002189 fluorescence spectrum Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 101001018064 Homo sapiens Lysosomal-trafficking regulator Proteins 0.000 description 1
- 102100033472 Lysosomal-trafficking regulator Human genes 0.000 description 1
- 235000010703 Modiola caroliniana Nutrition 0.000 description 1
- 244000038561 Modiola caroliniana Species 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/06—Zinc compounds
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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
- C07F15/02—Iron compounds
- C07F15/025—Iron compounds without a metal-carbon linkage
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/187—Metal complexes of the iron group metals, i.e. Fe, Co or Ni
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
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- Materials Engineering (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
A tetrahedral cage structure complex (I) has the following chemical formula:
Description
Technical Field
The invention belongs to the field of supermolecule metal complexes, and particularly relates to preparation and performance characterization of a tetrahedral cage complex.
Background
The supermolecule metal cage complex is a complex formed by metal ions and secondary components through molecular engineering. The structure of various coordinated supermolecules constructed by molecular engineering is characterized in that a certain space is arranged in the supermolecules, and guest molecules can be accommodated in the supermolecules, so that the supermolecules can be used as molecular containers, reactors and inductors. The method has important application value in the fields of molecular recognition and exchange, selective catalysis, chiral separation, luminescent probes, molecular machines, molecular devices and the like by utilizing the recognition effect and the three-dimensional effect between a host and an object. At present, the ligand molecule design of the cage-shaped complex is biased to novel organic macromolecules with high structural symmetry, so that the complex with a structure easy to detect and a large internal cavity volume is constructed. The cage-shaped complex provides a good way for the creation research of functional materials. In recent years, various designable, predictable and controllable precise and ingenious coordination self-assembly strategies emerge, and ideas and application examples are provided for the self-assembly of the coordination supermolecules directionally synthesized into different structures. Based on the development of the self-assembly supermolecule coordination compound, the synthesis method, the characterization technology and the application prospect of the modern supermolecule chemistry are promoted and enriched.
Disclosure of Invention
The invention aims to provide a tetrahedral cage structure complex.
Another object of the present invention is to provide a process for the preparation of the above complexes.
The technical scheme of the invention comprises the following steps:
a tetrahedral cage structure complex is shown as a general formula (I):
a process for the synthesis of the complex (I) according to claim 1. Taking p-nitrophenol as a raw material, carrying out nucleophilic substitution reaction on the p-nitrophenol and cyanuric chloride to obtain tri-p-nitrophenoxy s-triazine, and reducing the tri-p-nitrophenoxy s-triazine by iron powder to obtain tri-p-aminophenoxy s-triazine; synthesizing a target complex by using tri-p-aminophenoxy s-triazine, ferrous trifluoromethanesulfonate or zinc trifluoromethanesulfonate and 3-methylpyridine-2-formaldehyde through self-assembly. The reaction process is as follows:
the conditions in reaction (2) were: the reaction solvent can be selected from acetonitrile, methanol, pyridine and dioxane, and is preferably acetonitrile; the reaction temperature can be selected from 30-75 ℃, and preferably 30-55 ℃. The self-assembly synthesis method adopted by the invention can obtain the target product by one-step reaction, and is simple and easy to implement.
The complex (I) has stronger fluorescence property under the excitation of ultraviolet light, so that the complex can become a potential high-quality luminescent material.
Drawings
Fig. 1 shows the fluorescence spectrum of complex (I) (M ═ Fe); fig. 2 shows the fluorescence spectrum of complex (I) (M ═ Zn).
Detailed Description
Example 1
This example illustrates the preparation of tris-p-aminophenoxy s-triazine
Adding 3.00g (25.2mmol) of p-nitrophenol and 1g (25.2mmol) of sodium hydroxide into a 500mL four-neck flask containing 100mL of water and 20mL of acetone, magnetically stirring for 15min, slowly dropwise adding 100mL of acetone solution dissolved with 1.5g (8.2mmol) of cyanuric chloride under ice bath, reacting for 2h after the addition is finished, filtering, washing and drying to obtain 3.65g of white tri-p-nitrophenoxy-s-triazine with a melting point: 208 ℃ and 212 ℃.1H NMR(400MHz，CDCl3)：8.33(d，J＝8.76Hz，2H)，7.37(d，J＝9Hz，2H)，13C NMR(400MHz，CDCl3)：173.07，162.56，145.91，125.55，122.39。
Adding 1.78g (3.7mmol) of tris-p-nitrophenoxy s-triazine, 3g (55mmol) of ammonium chloride, 60mL of methanol and 20mL of water into a 250mL flask in sequence, stirring and heating to reflux, adding 3g (55mmol) of 100-mesh high-activity reduced iron powder for three times under stirring, filtering while hot after reacting for 2 hours, washing a filter cake with 10mL of hot methanol multiplied by 2, adjusting the pH of the obtained filtrate to 9 with sodium bicarbonate, filtering and desolventizing, recrystallizing the obtained crude product with methanol to obtain 1.12g of light yellow tris-p-aminophenoxy s-triazine, wherein the yield is 63%, and the melting point is as follows: 225 ℃ and 228 ℃.1H NMR(400MHz，CDCl3)：6.94(d，J＝8.76Hz，1H，Benzene-H)，6.65(d，J＝8.72Hz，1H，Benzene-H)，3.70(s，6H，NH2)，13C NMR(400MHz，DMSO)：174.09，146.88，142.24，122.07，114.64。
Example 2
This example illustrates the preparation of a tetrahedral cage complex and its fluorescence properties
(1) Preparation of Complex (I) (M ═ Fe)
In a 25mL flask were charged, in order, 25mg (0.062mmol) of tris-p-aminophenoxy-s-triazine, 22mg (0.062mmol) of ferrous trifluoromethanesulfonate, 22mg (0.186mmol) of 3-methylpyridine-2-carbaldehyde and 10mL of acetonitrile, N2The reaction is carried out for 12h at the temperature of 30 ℃ under protection. After the reaction is finished, 15mL of ether is added to separate out a solid, a mauve solid is obtained after centrifugal separation, and the product 33mg is obtained after ether washing and drying. The yield was 57.3%, the melting point > 300 ℃. Nuclear magnetic data1H NMR(400MHz，CD3CN): 9.03(s, 1H, imine-H), 8.14(d, J ═ 8.5Hz, 1H, pyridine-H), 7.62(t, J ═ 12.9Hz, 1H, pyridine-H), 7.48(d, J ═ 7.5Hz, 1H, pyridine-H), 7.21(d, J ═ 7.1Hz, 1H, Benzene-H), 7.04(d, J ═ 5.0Hz, 1H, Benzene-H), 5.82(d, J ═ 9.5Hz, 1H, Benzene-H), 5.21(d, J ═ 8.6Hz, 1H, Benzene-H), 2.82(s, 3H, Methyl-H), data (ESI-MS): m/z 383.6.
(2) Preparation of Complex (I) (M ═ Zn)
In a 25mL flask were charged 25mg (0.062mmol) of tris-p-aminophenoxy-s-triazine, 23mg (0.062mmol) of zinc trifluoromethanesulfonate, 22mg (0.186mmol) of 3-methylpyridine-2-carbaldehyde and 10mL of acetonitrile in this order, and reacted at 55 ℃ for 12 hours. After the reaction, 15mL of ether is added to separate out a solid, a white solid is obtained after centrifugal separation, and the product 37mg is obtained after ether washing and drying. The yield was 59.1%, the melting point > 300 ℃. Nuclear magnetic data1H NMR(400MHz，CD3CN)：8.73(s，1H，imine-H)，8.24(d，J＝7.8Hz，1H，pyridine-H)，7.77(t，J＝7.8Hz，1H，pyridine-H)，7.71(d，J＝4.2Hz，1H，pyridine-H)，7.44(d，J＝7.3Hz，2H，Benzene-H)，6.02(s，2H，Benzene-H)，2.69(s，3H，Methyl-H)，13C NMR(400MHz，CD3CN): 179.35, 156.08, 152.15, 151.71, 150.07, 149.26, 145.76, 134.80, 129.15, 127.47, 122.70, mass spectrometry data (ESI-MS): m/z 387.6.
(3) Measurement of fluorescent Property of Complex (I)
The fluorescence spectrum data of the conjugate (I) are shown in FIG. 1. As can be seen, the complex (I) (M ═ Fe) emits strong fluorescence at a wavelength of 416nm under the excitation of ultraviolet light; the complex (I) (M ═ Zn) emits strong fluorescence at the wavelength of 553nm under the excitation of ultraviolet light, and the complex (I) is proved to have good fluorescence characteristics.
Claims (3)
1. An imine complex with a tetrahedral cage structure, which has a structure shown as a general formula (I):
2. a process for the preparation of a complex of formula (I) as claimed in claim 1. Synthesizing a target complex by using tri-p-aminophenoxy s-triazine, ferrous trifluoromethanesulfonate or zinc trifluoromethanesulfonate and 3-methylpyridine-2-formaldehyde through self-assembly. The reaction process is as follows:
3. the production method according to claim 2, wherein: the reaction solvent in the reaction (1) is selected from acetonitrile, methanol, pyridine and dioxane, and is preferably acetonitrile; the reaction temperature in the reaction (1) is 30 to 75 ℃, and preferably 30 to 55 ℃.
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2018
- 2018-10-12 CN CN201811205540.8A patent/CN111039964A/en active Pending
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