CN109438420A - A kind of imines zinc s-triazine complex - Google Patents
A kind of imines zinc s-triazine complex Download PDFInfo
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- CN109438420A CN109438420A CN201811342524.3A CN201811342524A CN109438420A CN 109438420 A CN109438420 A CN 109438420A CN 201811342524 A CN201811342524 A CN 201811342524A CN 109438420 A CN109438420 A CN 109438420A
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- triazine
- complex
- zinc
- imines
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- 150000002466 imines Chemical class 0.000 title claims abstract description 8
- SWFCGZUVPAQCAK-UHFFFAOYSA-N 1,3,5-triazine zinc Chemical compound [Zn].C1=NC=NC=N1 SWFCGZUVPAQCAK-UHFFFAOYSA-N 0.000 title claims abstract description 7
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims abstract description 5
- 230000000694 effects Effects 0.000 claims abstract description 5
- -1 hexafluorophosphoric acid sodium Chemical compound 0.000 claims abstract description 4
- NGOCMUBXJDDBLB-UHFFFAOYSA-N trifluoromethanesulfonic acid;zinc Chemical compound [Zn].OS(=O)(=O)C(F)(F)F NGOCMUBXJDDBLB-UHFFFAOYSA-N 0.000 claims abstract description 4
- AHISYUZBWDSPQL-UHFFFAOYSA-N 6-methylpyridine-2-carbaldehyde Chemical compound CC1=CC=CC(C=O)=N1 AHISYUZBWDSPQL-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000001338 self-assembly Methods 0.000 claims abstract description 3
- 229910001415 sodium ion Inorganic materials 0.000 claims abstract description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 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
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 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 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WEVYAHXRMPXWCK-FIBGUPNXSA-N acetonitrile-d3 Chemical compound [2H]C([2H])([2H])C#N WEVYAHXRMPXWCK-FIBGUPNXSA-N 0.000 description 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- YXVLPSYQESBKQE-UHFFFAOYSA-N N1=CN=CN=C1.[O].NC1=CC=CC=C1 Chemical compound N1=CN=CN=C1.[O].NC1=CC=CC=C1 YXVLPSYQESBKQE-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000011365 complex material Substances 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001506 fluorescence spectroscopy Methods 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 230000005389 magnetism Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- C09K2211/18—Metal complexes
- C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
Abstract
A kind of imines zinc s-triazine complex (I), chemical formula is as follows:
Description
Technical field
The present invention relates to a kind of organometallic complex and preparation method thereof, in particular to nitrogenous s-triazine metal
Organic coordination compound and preparation method thereof is exactly a kind of imines zinc s-triazine complex and its synthetic method.
Background technique
The development of metal organic coordination super molecular compound is advanced by leaps and bounds, and more and more structure novels, function are unique
Organometallic complex is able to discovery and synthesis.Metal organic complex is that metal ion and organic secondary component pass through molecule work
A kind of complex that journey is formed.Self-assembling technique in molecular engineering combines coordinate bond, the orientation of covalent bond and strength advantage,
And flexible, reversible, the dynamic, synergistic effect of intermolecular linkages and the non-covalent bond such as hydrogen bond, π-π interaction；This fit on
The assembling and steric configuration that can also influence complex in journey using itself binding property of some anion and diameter degree, by yin from
The template effect of sub- driving structure conversion, forms the stable complex structure of specificity, enriches the conjunction of metal organic complex
At method and type.Metal organic complex is with its novel structure in catalysis, electrochemistry, absorption, ion exchange and magnetism etc.
Aspect has potential application prospect；Furthermore metal organic complex material has the high-luminous-efficiency and inorganic matter of organic matter concurrently
The features such as stability is good, thus be considered as a kind of luminescent material for most having application prospect.In recent years, various Luminescent metal complexes
Object is synthesized in succession, and is applied to electroluminescent device.
Summary of the invention
It is an object of the present invention to provide a kind of imines zinc s-triazine structure complexs.
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 imines zinc s-triazine complex, structure is as shown in logical formula (I):
The synthetic method of complex (I) according to claim 1.It is passed through by raw material and Cyanuric Chloride of p-nitrophenol
Nucleophilic substitution obtains three p-nitrophenyl oxygroup s-triazine, obtains three p-aminophenyl oxygroup s-triazine through iron powder reducing；With three pairs
Amino-benzene oxygen s-triazine, trifluoromethanesulfonic acid zinc and 6- picoline -2- formaldehyde lead under hexafluorophosphoric acid sodium ion template effect
Cross self assembly complex.Its reaction process is as follows:
React the condition in (2) are as follows: the optional acetonitrile of reaction dissolvent, methanol, pyridine, dioxane, preferably acetonitrile；Reaction
Temperature is chosen as 30~75 DEG C, preferably 70 DEG C.The self assembling process of synthesizing that the present invention uses, single step reaction obtain target product,
Post-processing is 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 is complex (I) fluorescence spectrum
Specific embodiment
Embodiment 1
This example illustrates the preparation of three p-aminophenyl oxygroup s-triazine
P-nitrophenol 3.00g (25.2mmol) and sodium hydroxide 1g (25.2mmol) are added to water containing 100mL and 20mL
The 500mL four-hole boiling flask of acetone after magnetic agitation 15min, is slowly added dropwise under ice bath dissolved with Cyanuric Chloride 1.5g (8.2mmol)
100mL acetone soln, finish reaction 2h, be filtered, washed, dry after obtain the three p-nitrophenyl oxygroup equal three of white of 3.65g
Piperazine, fusing point: 208-212 DEG C.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.
By three p-nitrophenyl oxygroup s-triazine 1.78g (3.7mmol), ammonium chloride 3g (55mmol), methanol 60mL and water
20mL is sequentially added in 250mL flask, is stirred, is heated to reflux, and 100 mesh high activity reduced iron powder 3g are added in three times under stiring
(55mmol) is filtered while hot after reacting 3h, washs filter cake with hot methanol 10mL × 2, gained filtrate with sodium bicarbonate tune pH to 9,
Filtering, precipitation, obtained crude product with methanol recrystallization, obtain the faint yellow three p-aminophenyls oxygroup s-triazine of 1.12g, yield
63%, fusing point: 225-228 DEG C.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, 1H, NH2),13C NMR (400MHz, DMSO): 174.09,146.88,
142.24 122.07,114.64.
Embodiment 2
This example illustrates that the preparation of imines zinc structural coordination compound and fluorescence property measure
(1) prepared by complex
Three p-aminophenyl oxygroup s-triazine of 25mg (0.062mmol), 34mg are sequentially added in 25mL flask
(0.093mmol) trifluoromethanesulfonic acid zinc, 78mg (0.46mmol) sodium hexafluoro phosphate, 6- picoline -2- formaldehyde 22mg
(0.186mmol) and 10mL acetonitrile, 70 DEG C of reaction 12h.Reaction is finished, and is added 15mL ether that solid is precipitated, is obtained after centrifuge separation white
Color solid, ether washing, drying obtain product 39mg.Yield is 62.3%, 300 DEG C of fusing point >.Nuclear magnetic data1H NMR
(400MHz, CD3CN): 8.40 (s, 1H, imine-H), 8.35 (t, J=7.8Hz, 1H, pyridine-H), 8.10 (d, J=
7.5Hz, 1H, pyridine-H), 7.87 (d, J=7.9Hz, 1H, pyridine-H), 7.43 (s, 1H, Benzene-H), 7.13
(s, 1H, Benzene-H), 5.95 (s, 1H, Benzene-H), 5.26 (s, 1H, Benzene-H),13C NMR (400MHz,
CD3CN): 179.46,171.52,166.86,155.55,152.18,151.38,146.10,138.57,134.88,127.02.
(2) complex fluorescent performance measurement
The fluorescence data of complex (I) is shown in attached drawing 1.As seen from the figure, complex (I) is under the excitation of ultraviolet light,
Wavelength is to have issued hyperfluorescence at 537nm, shows the complex (I) with good fluorescent characteristic.
Claims (3)
1. a kind of imines zinc s-triazine 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 oxygroup s-triazine, trifluoro
Methanesulfonic acid zinc and 6- picoline -2- formaldehyde pass through self assembly complex under hexafluorophosphoric acid sodium ion template effect.Its
Reaction process is as follows:
3. preparation method according to claim 2, in which: the optional acetonitrile of reaction dissolvent, methanol, pyridine, dioxane, it is excellent
It is selected as acetonitrile；Reacting the reaction temperature in (1) is 30~75 DEG C, preferably 70 DEG C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811342524.3A CN109438420A (en) | 2018-11-08 | 2018-11-08 | A kind of imines zinc s-triazine complex |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811342524.3A CN109438420A (en) | 2018-11-08 | 2018-11-08 | A kind of imines zinc s-triazine complex |
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| Publication Number | Publication Date |
|---|---|
| CN109438420A true CN109438420A (en) | 2019-03-08 |
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|---|---|---|---|
| CN201811342524.3A Pending CN109438420A (en) | 2018-11-08 | 2018-11-08 | A kind of imines zinc s-triazine complex |
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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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| US6562973B1 (en) * | 2001-08-15 | 2003-05-13 | Equistar Chemicals, Lp | Method for making late transition metal catalysts for olefin polymerization |
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| CN103224508A (en) * | 2013-05-23 | 2013-07-31 | 哈尔滨工业大学 | Organic red-light material o-pyridyl monoimido zinc/mercury complex and preparation method thereof |
| CN107417709A (en) * | 2017-08-01 | 2017-12-01 | 合肥工业大学 | A kind of preparation of Zn complex crystal and its synthetic method |
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-
2018
- 2018-11-08 CN CN201811342524.3A patent/CN109438420A/en active Pending
Patent Citations (5)
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| US6562973B1 (en) * | 2001-08-15 | 2003-05-13 | Equistar Chemicals, Lp | Method for making late transition metal catalysts for olefin polymerization |
| CN101240168A (en) * | 2008-03-19 | 2008-08-13 | 哈尔滨工业大学 | Blue light organic luminescent material and preparation 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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