CN108912096A - A kind of leptospira structure imines iron complex - Google Patents
A kind of leptospira structure imines iron complex Download PDFInfo
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- CN108912096A CN108912096A CN201810684208.8A CN201810684208A CN108912096A CN 108912096 A CN108912096 A CN 108912096A CN 201810684208 A CN201810684208 A CN 201810684208A CN 108912096 A CN108912096 A CN 108912096A
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- Prior art keywords
- complex
- pyridine
- leptospira structure
- iron complex
- leptospira
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- 241000589902 Leptospira Species 0.000 title claims abstract description 10
- -1 imines iron complex Chemical class 0.000 title claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- COIXVMRSSZXQKF-UHFFFAOYSA-N 4-phenyl-1,3,5-triazin-2-amine Chemical compound NC1=NC=NC(C=2C=CC=CC=2)=N1 COIXVMRSSZXQKF-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000001338 self-assembly Methods 0.000 claims abstract description 6
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims abstract description 5
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 claims abstract description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 229910021645 metal ion Inorganic materials 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000013110 organic ligand Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- YBAZINRZQSAIAY-UHFFFAOYSA-N 4-aminobenzonitrile Chemical compound NC1=CC=C(C#N)C=C1 YBAZINRZQSAIAY-UHFFFAOYSA-N 0.000 description 1
- 244000061458 Solanum melongena Species 0.000 description 1
- WEVYAHXRMPXWCK-FIBGUPNXSA-N acetonitrile-d3 Chemical compound [2H]C([2H])([2H])C#N WEVYAHXRMPXWCK-FIBGUPNXSA-N 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 238000001506 fluorescence spectroscopy Methods 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- BGOFCVIGEYGEOF-UJPOAAIJSA-N helicin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=CC=C1C=O BGOFCVIGEYGEOF-UJPOAAIJSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 150000001455 metallic ions Chemical class 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 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
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C09K2211/187—Metal complexes of the iron group metals, i.e. Fe, Co or Ni
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
A kind of leptospira structure imines iron complex (I), chemical formula is as follows：
Description
One, technical field
The invention belongs to metal organic complex fields, and in particular to a kind of preparation of leptospira structure imines iron complex and
The research of its fluorescence property.
Two, background technique
During most of leptospira structure complex appears in self assembly tetrahedral structure cage coordination compound.
This kind of complexs can be by C3The organic molecule of symmetry is obtained with metal ion self assembly, can also be by linear axes pair
Claim ligand molecular to obtain with metal ion self assembly, mainly by N → M coordinate bond and is matched by upper and lower two metal ions
Dynamic C=N covalent bond is formed as node in body molecule, constructs stable spiral shell while forming these stable chemical bonds
Revolve body complex.Since in a complex molecule, only there are two metallic ion coordinations, therefore do not have in organic ligand molecule
The one end for forming coordination will expose, and form similar to spiral helicine complex.The metal ion of synthetic compound has
Fe2+, Zn2+, Co2+, Ni2+, Cu2+/Cu1+, Pt2+Deng, and the design of organic ligand is more prone to the high molecule of those symmetry
Such as linear type, plane trigonometry type molecule.It selects different amine and aldehydes as secondary component, can design to obtain different symmetry
With coordination the number of teeth ligand, the coordination of bind metal ion, can permutation and combination form different geometry topological structures.These geometry
It is high to construct symmetry, is easy to structural characterization, and there are significant internal cavities can accommodate some guest molecules, therefore can make
For cell reservoirs, reactor, inductor.Using the recognition effect between host-guest, stereoeffect, molecular recognition with exchange,
The fields such as selective catalysis, chiral separation, luminescence probe and molecule machine and molecular device have potential application.
Such complex will provide a kind of good approach for the innovative research of functional material.
Summary of the invention
It is an object of the present invention to provide a kind of leptospira structure imines iron 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 leptospira structure imines iron complex structure is as shown in logical formula (I)：
The synthetic method of complex (I) according to claim 1.It is raw material in trifluoro methylsulphur using p-aminophenyl formonitrile HCN
Three p-aminophenyl s-triazine are synthesized under acid catalysis；With three p-aminophenyl s-triazine, trifluoromethanesulfonic acid ferrous iron and pyridine -2- first
Aldehyde passes through self assembly title complex.Its reaction process is as follows：
Reaction (2) in condition be：The optional acetonitrile of reaction dissolvent, methanol, pyridine, dioxane, preferably acetonitrile；Reaction
Temperature is chosen as 30~75 DEG C, preferably 45~60 DEG C.The self assembling process of synthesizing that the present invention uses, single step reaction obtain target production
Object, post-processing are simple.
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) fluorescence spectrum
Specific embodiment
Embodiment 1
This example illustrates the preparation of three p-aminophenyl s-triazine
P-aminophenyl formonitrile HCN 1.18g (10mmol) is added to 50mL four-hole boiling flask, and 25mL dichloromethane is added under magnetic agitation
Alkane is dissolved, and 4mL (45mmol) trifluoromethanesulfonic acid is slowly added dropwise under ice bath, finishes N2 protection reaction for 24 hours.Reaction terminates
Afterwards, liquid separation takes lower layer's yellow oil reservoir, adds and is adjusted to pH with 50% sodium hydroxide solution as 9-11 after 20mL water, pale yellow colored solid is precipitated
Body is filtered, is washed, drying obtains product 993mg, yield 85.0%.Fusing point：300 DEG C of >.1H NMR (400MHz, DMSO)：
8.38 (d, J=2.1Hz, 6H, Benzene-H), 6.71 (d, J=8.5Hz, 6H, Benzene-H), 5.90 (s, 6H, NH2).Member
Element analysis data：C21H18N6, theoretical value：C, 71.17；H, 5.12；N, 23.71.Actual value：C, 71.15；H, 5.13；N,
23.72.IR(KBr)：3321,3214,3030,1637,1604,813cm-1。
Embodiment 2
This example illustrates preparation and the fluorescence property of leptospira structure imines iron complex
(1) prepared by complex
Three p-aminophenyl s-triazine of 106.3mg (0.3mmol), 70.8mg are sequentially added in 25mL flask
(0.2mmol) trifluoromethanesulfonic acid ferrous iron, 64.2mg pyridine-2-formaldehyde (0.6mmol) and 10mL acetonitrile, N2Protect 55 DEG C of reactions
12h.Reaction is finished, and adds 15mL ether that solid is precipitated, and aubergine solid product is obtained after centrifuge separation, and ether washing, drying obtain
Product 98mg.Yield is 57.3%, 300 DEG C of fusing point >.Nuclear magnetic data1H NMR (400MHz, CD3CN)：9.00 (s, imine-
H), 8.71 (d, J=6.5Hz, Ph-H), 8.65 (d, J=6.4Hz, pyridine-H), 8.51 (m, Ph-H&pyridine-H),
7.85 (s, pyridine-H), 7.47 (d, J=4.5Hz, pyridine-H), 6.80 (d, J=7.9Hz, Ph-H), 6.03 (d, J
=6.4Hz, Ph-H), 5.03 (s, 1H, amine), 4.70 (d, J=7.5Hz, Ph-H).Mass spectrometric data (ESI-MS)：m/z
427.58。
(2) complex fluorescent performance measurement
Attached drawing 1 is seen with the fluorescence data with object (I).As seen from the figure, the complex is under the excitation of ultraviolet light, in wave
Stronger fluorescence is had issued at a length of 296nm and 583nm, is shown this and is matched with object (I) with good fluorescent characteristic.
Claims (3)
1. a kind of leptospira structure imines iron complex, structure is as shown in logical formula (I)：
2. a kind of preparation method of formula (I) compound logical as described in claim 1.With three p-aminophenyl s-triazine, fluoroform
Sulfonic acid ferrous iron and pyridine-2-formaldehyde pass through self assembly title complex.Its reaction process is as follows：
3. preparation method according to claim 2, wherein：React (1) in reaction dissolvent be selected from acetonitrile, methanol, pyridine,
Dioxane, preferably acetonitrile；Reacting the reaction temperature in (1) is 30~75 DEG C, preferably 45~60 DEG C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810684208.8A CN108912096A (en) | 2018-06-22 | 2018-06-22 | A kind of leptospira structure imines iron complex |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810684208.8A CN108912096A (en) | 2018-06-22 | 2018-06-22 | A kind of leptospira structure imines iron complex |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN108912096A true CN108912096A (en) | 2018-11-30 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810684208.8A Pending CN108912096A (en) | 2018-06-22 | 2018-06-22 | A kind of leptospira structure imines iron complex |
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| Country | Link |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114656399A (en) * | 2022-03-15 | 2022-06-24 | 南京工业大学 | Cavity spirochete imine silver complex |
-
2018
- 2018-06-22 CN CN201810684208.8A patent/CN108912096A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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: 20181130 |