CN110041308A - A kind of high symmetry sandwich structure imines Zn complex - Google Patents
A kind of high symmetry sandwich structure imines Zn complex Download PDFInfo
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- CN110041308A CN110041308A CN201810057001.8A CN201810057001A CN110041308A CN 110041308 A CN110041308 A CN 110041308A CN 201810057001 A CN201810057001 A CN 201810057001A CN 110041308 A CN110041308 A CN 110041308A
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- 150000002466 imines Chemical class 0.000 title claims abstract description 12
- 239000011701 zinc Substances 0.000 claims abstract description 12
- 238000002360 preparation method Methods 0.000 claims abstract description 10
- 238000001338 self-assembly Methods 0.000 claims abstract description 8
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims abstract description 7
- -1 m-aminophenyl Chemical group 0.000 claims abstract description 6
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 claims abstract description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 3
- UFITZXXHLWZPNO-UHFFFAOYSA-N perchloric acid;hexahydrate Chemical compound O.O.O.O.O.O.OCl(=O)(=O)=O UFITZXXHLWZPNO-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 16
- 239000013078 crystal Substances 0.000 claims description 11
- 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- NJXPYZHXZZCTNI-UHFFFAOYSA-N 3-aminobenzonitrile Chemical compound NC1=CC=CC(C#N)=C1 NJXPYZHXZZCTNI-UHFFFAOYSA-N 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- 238000002447 crystallographic data Methods 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- WEVYAHXRMPXWCK-FIBGUPNXSA-N acetonitrile-d3 Chemical compound [2H]C([2H])([2H])C#N WEVYAHXRMPXWCK-FIBGUPNXSA-N 0.000 description 2
- 150000001412 amines Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000013110 organic ligand Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 230000005260 alpha ray Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000001506 fluorescence spectroscopy Methods 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000013517 stratification Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- RJFSDTDWWBECIL-UHFFFAOYSA-N trifluoro(methyl)-$l^{4}-sulfane Chemical compound CS(F)(F)F RJFSDTDWWBECIL-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- PADPILQDYPIHQQ-UHFFFAOYSA-L zinc;diperchlorate;hexahydrate Chemical compound O.O.O.O.O.O.[Zn+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O PADPILQDYPIHQQ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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
-
- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
-
- 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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
Abstract
A kind of high symmetry sandwich structure imines Zn complex (I), chemical formula is as follows:
Description
Technical field
The present invention relates to a kind of high symmetry sandwich structure imines Zn complexes and preparation method thereof, in particular to containing Asia
Metal organic complex of amine structure and preparation method thereof is exactly a kind of high symmetric metal organic coordination compound and its preparation
Method.
Background technique
Super molecular compound containing imine structure is one kind that metal ion and imines organic ligand are formed by coordinate bond
Complex.It is structurally characterized in that inside has certain space, can accommodate some guest molecules, therefore can be used as molecule appearance
Device, reactor, inductor.Using the recognition effect between host-guest, stereoeffect, molecular recognition with exchange, selectivity is urged
The fields such as change, chiral separation, luminescence probe and molecule machine and molecular device have potential application.In recent years, if
Count and construct the high great interest that people are caused to the super molecular complex of property.And the design of organic ligand is more prone to height
Symmetrical structure such as linear type, plane trigonometry type molecule.The amine and aldehydes for selecting different high symmetry as secondary component,
The pre-designed symmetrical ligand of height can be obtained, with metal cations Fe2+, Zn2+, Co2+, Ni2+, Cu2+/Cu1+, Pt2+Coordination, can arrange group
Conjunction forms different geometry topological structures, and symmetry is high, and there is certain cavity in inside.These super molecular compounds can construct
At macrocyclic structure, helical structure, tetrahedral structure, octahedral structure, prism structure, cube structure etc..It is super containing imine structure
Molecular complex can form dynamic C=N covalent bond during self assembly, it have good dynamics invertibity and
Preferable bond strength forms single thermodynamic advantages product so that Coordinate self-assembly direction according to expectation and mode carry out.
The development of coordination supramolecule chemistry is largely dependent upon the development of coordination supramolecule self-assembling method.Wherein, based on chelating
The substep self assembly strategy of guiding role, steric hindrance limitation and hsab theory, which becomes, constructs the cooperation of metal caged supermolecule
A kind of usability methods of object.It is various in recent years design, can be predicted, it is regulatable that precisely cleverly Coordinate self-assembly strategy gushes
Existing, the self assembly for the coordination supramolecule of controlled syntheses different structure provides thinking and application example.The hair of supramolecular chemistry
Exhibition has reached unprecedented level, greatly promotes and enrich modern supramolecular chemistry synthetic method and technology.
Summary of the invention
It is an object of the present invention to provide a kind of high symmetry sandwich structure imines Zn complexes.
It is a further object of the present invention to provide the preparation methods of above-mentioned complex.
Purpose of the present invention technical solution is as follows:
A kind of high symmetry sandwich structure imines Zn complex, structure is as shown in logical formula (I):
Complex (I) according to claim 1, at 25 DEG C on Bruker Apex II CCD single crystal diffractometer,
With MoK alpha ray (λ=0.71073) with ω-θ scanning mode collection diffraction data, it is characterised in that: crystal category monoclinic crystal
System, space group P-1 (#2).Cell parameter: a=21.280 (12)B=26.727 (15)C=35.29 (2)α=
90.00 (2) °, β=90.00 (2) °, γ=90.00 (2) °.
The synthetic method of complex (I) according to claim 1.It is raw material through trifluoro methylsulphur using m-aminophenyl formonitrile HCN
Acid catalysis synthesizes three m-aminophenyl base s-triazine；It is logical with three m-aminophenyl base s-triazine, perchlorate hexahydrate's zinc and pyridine-2-formaldehyde
Cross self assembly title complex.Its reaction process is as follows:
React the condition in (2) are as follows: the optional acetonitrile of reaction dissolvent, tetrahydrofuran, pyridine, dioxane, preferably acetonitrile；
Reaction temperature is 20~75 DEG C, preferably 20~30 DEG C.The self assembling process of synthesizing that the present invention uses, simple process, one-step synthesis
Target product, it is easy to operate.
Complex (I) issues stronger fluorescence under the excitation of ultraviolet light, has become a kind of potential high-quality luminous
Material.
Detailed description of the invention
Fig. 1 be with object (I) molecular structure ellipsoid figure
Fig. 2 be with object (I) structure cell accumulation graph
Fig. 3 be with object (I) fluorescence spectrum
Specific embodiment
Embodiment 1
This example illustrates the preparation of three m-aminophenyl base s-triazine
25mL four-hole boiling flask is added after m-aminophenyl formonitrile HCN 2.835g (0.024mol) plus the dissolution of 15mL methylene chloride.Magnetic force
Under stirring, the trifluoromethanesulfonic acid of 10mL (0.113mol) is slowly added dropwise into four-hole boiling flask with constant pressure funnel, N2 protection
Reaction is for 24 hours.Stratification separates supernatant liquor, leaves and takes lower layer.The sodium hydroxide solution of 2mol/L is added dropwise in lower liquid
It is 9-11 to pH value of solution, light yellow solid is precipitated, filtering, recrystallization, drying obtains product 1.73g, yield 60.1%.Fusing point:
300 DEG C of >.1H NMR (400MHz, CD3CN): 8.06 (m, 3H, Ph-H), 8.03 (m, 3H, Ph-H), 7.32 (dd, J=9.8,
5.8Hz, 3H, Ph-H), 6.93 (ddd, J=7.9,2.4,0.9Hz, 3H, Ph-H), 4.43 (s, 6H, amine-H).Elemental analysis
Data: C21H18N6, theoretical value: C, 71.17；H, 5.12；N, 23.71.Actual value: C, 71.07；H, 5.20；N, 23.68.IR
(cm-1): 3339.50,1607.90,1518.68,1453.68,1358.02.
Embodiment 2
This example illustrates the preparation and crystal culture of high symmetry sandwich structure imines Zn complex
Tri- m-aminophenyl base s-triazine (70.8mg) of 0.2mmol is put into 25mL flask, addition 10mL anhydrous acetonitrile,
0.3mmol perchlorate hexahydrate zinc (111.7mg) and 0.6mmol pyridine-2-formaldehyde (64.2mg) react 15 hours at 25 DEG C.
20mL ether is added in end of reaction, and solid is precipitated, filtering, ether washs, drying obtains white complex solid.Yield is
90%, fusing point is greater than 300 DEG C.Elemental analysis data C78H78Zn3N18O36C16, theoretical value: C 41.59；H:3.49；N:11.20.
Measured value: C 41.28；H:3.39；N:10.96.Nuclear magnetic data1H NMR (400MHz, CD3CN) 68.65 (s, 3H, imine-
H), 8.49 (d, J=3.7Hz, 3H, pyridine-H), 8.44 (t, J=7.7Hz, 3H, pyridine-H), 8.28 (d, J=
7.6Hz, 3H, pyridine-H), 8.20 (d, J=7.6Hz, 3H, Ph-H), 7.99 (dd, J=7.3,5.5Hz, 3H,
Pyridine-H), 7.93 (s, 3H, Ph-H), 7.72 (t, J=7.8Hz, 3H, Ph-H), 7.46 (d, J=7.3Hz, 3H, Ph-
H) mass spectrometric data (CH3CN): m/z [(I) (H2O)6]6+Peak, 258.9.
White needles complex monocrystal is obtained using ether diffusion method culture.Crystal is rinsed 3 times with petroleum ether, vacuum drying
30min is tested for crystal structure.Table 1- table 3, Fig. 1-Fig. 2 are crystal characterization data.
1 complex of table (I) crystal parameter and structural parameters
2 complex of table (I) main bond distance
The main bond angle (°) of 3 complex of table (I)
Fig. 3 is with the fluorescence data with object (I).As seen in Figure 3, the complex crystal swashing in ultraviolet light
It gives, is to have issued stronger fluorescence at 405nm in wavelength, shows this and match with object (I) with good fluorescent characteristic.
Claims (5)
1. a kind of high symmetry sandwich structure imines Zn complex, structure is as shown in logical formula (I):
2. complex (I) according to claim 1, at 25 DEG C on Bruker Apex II CCD single crystal diffractometer, use
MoK alpha rayDiffraction data is collected with ω-θ scanning mode, it is characterised in that: crystal category monoclinic system, it is empty
Between group P-1 (#2).Cell parameter:α=90.00
(2) °, β=90.00 (2) °, γ=90.00 (2) °.
3. a kind of preparation method of formula (I) compound logical as described in claim 1.It is raw material through fluoroform using m-aminophenyl formonitrile HCN
Sulfonic acid catalyzes and synthesizes three m-aminophenyl base s-triazine；With three m-aminophenyl base s-triazine, perchlorate hexahydrate's zinc and pyridine-2-formaldehyde
Pass through self assembly title complex.Its reaction process is as follows:
4. preparation method according to claim 3, in which: reaction (2) in reaction dissolvent be selected from acetonitrile, tetrahydrofuran,
Pyridine, dioxane, preferably acetonitrile.
5. preparation method according to claim 3, in which: reaction (2) in reaction temperature be 20~75 DEG C, preferably 20
~30 DEG C.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111592523A (en) * | 2020-05-07 | 2020-08-28 | 南京工业大学 | Layered structure sym-triazine imine zinc complex |
| CN114656399A (en) * | 2022-03-15 | 2022-06-24 | 南京工业大学 | Cavity spirochete imine silver complex |
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| CN105418651A (en) * | 2016-01-05 | 2016-03-23 | 天津师范大学 | Potential fluorescent material tetraphenyl ethylene tetratriazole zinc silicofluoride complex and preparing method thereof |
| CN105669715A (en) * | 2016-01-05 | 2016-06-15 | 天津师范大学 | 1,4-Di(4-(1H-1,2,4-triazole-1-yl)phenyl)piperazine zinc complex monocrystal and application thereof |
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2018
- 2018-01-16 CN CN201810057001.8A patent/CN110041308A/en active Pending
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| CN104610297A (en) * | 2015-02-26 | 2015-05-13 | 天津师范大学 | Triiodo-benzene aniline triazole zinc complex with potential fluorescent material and preparation method thereof |
| CN105418651A (en) * | 2016-01-05 | 2016-03-23 | 天津师范大学 | Potential fluorescent material tetraphenyl ethylene tetratriazole zinc silicofluoride complex and preparing method thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111592523A (en) * | 2020-05-07 | 2020-08-28 | 南京工业大学 | Layered structure sym-triazine imine zinc complex |
| CN114656399A (en) * | 2022-03-15 | 2022-06-24 | 南京工业大学 | Cavity spirochete imine silver complex |
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Application publication date: 20190723 |