CN107337688A - A kind of europium organic backbone complex and preparation method thereof - Google Patents
A kind of europium organic backbone complex and preparation method thereof Download PDFInfo
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- CN107337688A CN107337688A CN201710564099.1A CN201710564099A CN107337688A CN 107337688 A CN107337688 A CN 107337688A CN 201710564099 A CN201710564099 A CN 201710564099A CN 107337688 A CN107337688 A CN 107337688A
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- 229910052693 Europium Inorganic materials 0.000 title claims abstract description 26
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 238000010668 complexation reaction Methods 0.000 title abstract description 3
- 239000013078 crystal Substances 0.000 claims abstract description 17
- 239000000463 material Substances 0.000 claims abstract description 9
- 230000003287 optical effect Effects 0.000 claims abstract description 7
- 238000001291 vacuum drying Methods 0.000 claims abstract description 6
- 229910016644 EuCl3 Inorganic materials 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims abstract description 3
- 229910001220 stainless steel Inorganic materials 0.000 claims description 6
- 239000010935 stainless steel Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 2
- 238000010792 warming Methods 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract description 26
- VNVRVVMDBBKLJQ-UHFFFAOYSA-N C(C=1C(C(=O)OCCCCCCCC)=CC=CC1)(=O)OCCCCCCCC.CC1=C(O)C=CC=C1O Chemical compound C(C=1C(C(=O)OCCCCCCCC)=CC=CC1)(=O)OCCCCCCCC.CC1=C(O)C=CC=C1O VNVRVVMDBBKLJQ-UHFFFAOYSA-N 0.000 abstract description 5
- 238000000034 method Methods 0.000 abstract description 5
- 238000006862 quantum yield reaction Methods 0.000 abstract description 4
- VPMPLMMWRGPERB-UHFFFAOYSA-N [O].C(=O)O.C1=CC=CC=C1 Chemical compound [O].C(=O)O.C1=CC=CC=C1 VPMPLMMWRGPERB-UHFFFAOYSA-N 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 229910052761 rare earth metal Inorganic materials 0.000 description 8
- 150000002500 ions Chemical class 0.000 description 7
- YAVVGPBYBUYPSR-UHFFFAOYSA-N benzene;oxygen Chemical compound [O].C1=CC=CC=C1 YAVVGPBYBUYPSR-UHFFFAOYSA-N 0.000 description 6
- -1 rare earth ion Chemical class 0.000 description 6
- 230000007704 transition Effects 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 150000002910 rare earth metals Chemical class 0.000 description 4
- 230000005284 excitation Effects 0.000 description 3
- 238000002189 fluorescence spectrum Methods 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 238000000634 powder X-ray diffraction Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- ZTMADXFOCUXMJE-UHFFFAOYSA-N 2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC=C1O ZTMADXFOCUXMJE-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000001857 fluorescence decay curve Methods 0.000 description 2
- ASHGTJPOSUFTGB-UHFFFAOYSA-N methyl resorcinol Natural products COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 238000002447 crystallographic data Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- LNBHUCHAFZUEGJ-UHFFFAOYSA-N europium(3+) Chemical compound [Eu+3] LNBHUCHAFZUEGJ-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910001428 transition metal ion Inorganic materials 0.000 description 1
Classifications
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/003—Compounds containing elements of Groups 3 or 13 of the Periodic Table without C-Metal linkages
-
- 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
- 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
-
- 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
- C09K2211/182—Metal complexes of the rare earth metals, i.e. Sc, Y or lanthanide
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
Abstract
The invention discloses a kind of europium organic backbone complex and preparation method thereof, the chemical formula of complex is：[Eu(L)(DMF)2]n, wherein H3L is 5 (4 ' formic acid benzene oxygen) methylresorcinol dioctyl phthalate, DMF N, N ' dimethylformamides.The complex can be made by the hot method of dimethylformamide：The ratio between amount by material is 1:1.5 H3L parts and EuCl3Add in the DMF of certain volume, after being stirred at room temperature 30 minutes, 120 DEG C of reaction 72h of keeping temperature in closed reactor.Room temperature cools down, and obtains colourless bulk crystals, washs, vacuum drying, yield 76%.Complex of the present invention can send out stronger feature feux rouges when being excited with the light of 395nm wavelength, and CIE chromaticity coordinates is (0.5859,0.3178), its fluorescence lifetime is 2.535ns, and quantum yield is up to 93.0%, therefore the complex can be used as potential optical material.
Description
Technical field
The present invention relates to rare earth metal complex, and in particular to a kind of europium organic backbone complex, particularly one kind are based on
The europium complex and its system with luminosity that europium (III) ion and 5- (4 '-formic acid benzene oxygen) methylresorcinol dioctyl phthalate are constructed
Preparation Method.
Background technology
Rare earth metal complex is due to multifrequency natures such as light, electricity, magnetic, in field tables such as luminous, catalysis, biological medicines
Reveal wide application prospect, wherein organolanthanide complexes as embedded photoluminescent material with traditional phosphor phase
Than due to rare earth ion possessed unique texture and property in itself, making it after coordinating with organic ligand, there is luminous intensity
Height, fluorescence color is pure, required excitation energy is low, fluorescence efficiency is high, is soluble in the advantages that organic media, thus is considered as most
There is a kind of luminescent material of application prospect.
Organic polycarboxylic acid part has stronger coordination ability, is widely used in preparing organolanthanide complexes.5-
(4 '-formic acid benzene oxygen) methylresorcinol dioctyl phthalate has good photo and thermal stability and hair as a kind of flexible organic carboxyl acid part
Optical property, particularly when itself and the transition metal ions with d10 electronic structures or rare earth ion are coordinated to form complex
Afterwards, there is high application value in optical material field.Up to the present, based on 5- (4 '-formic acid benzene oxygen) methylresorcinol two
The rare earth metal complex that formic acid is constructed yet there are no report.
The content of the invention
It is an object of the invention to provide it is a kind of can be as the europium organic backbone complex of optical material and its preparation side
Method.
A kind of europium organic backbone complex provided by the invention, its molecular formula are：[Eu (L) (DMF) 2] n, wherein H3L be
5- (4 '-formic acid benzene oxygen) methylresorcinol dioctyl phthalate, DMF N, N '-dimethyl formamide；Structural formula is：
The crystal of the complex belongs to monoclinic system, space group C2/c, cell parameter： α=γ=90 °, β=99.05 (6) °.The coordination mode of europium ion is matched somebody with somebody for nine in the complex
Position, each Eu (III) ions and nine oxygen are coordinated, and two of which oxygen (O1, O2) is from a chelating L3-Part, five oxygen (O4,
O5, O6, O6A, O7) come from four bridging L3-Part, the DMF molecules that two other oxygen (O8, O9) is coordinated from two end groups, i.e.,
The complex is to be connected adjacent ligand anion by coordinate bond, finally constitutes tridimensional network.Eu-O bond distance
Scope beX-ray powder diffraction confirms crystal prototype stable homogeneous.Under room temperature condition, use
395nm excitation wavelength excites the solid complexes, as a result shows, complex goes out at 592nm, 617nm, 651nm, 695nm
Existing Eu (III) ions characteristic emission peak caused by f-f transition, is attributed to Eu (III) ion respectively5D0→7F1,5D0→7F2,5D0→7F3,5D0→7F4Characteristic transition.Wherein 617nm is Eu (III) ion5D0→7F2Maximum transition emission peak, says
The energy transfer efficiency of bright part to rare earth ion is higher.By the digital photograph of ultra violet lamp, complex can be observed and show
The stronger feux rouges features of Eu (III) are shown.The europium complex of the present invention may be used as optical material.
The present invention provides a kind of preparation method of europium organic backbone complex, comprises the following steps：
(1) it is 1 by mol ratio:1~1.5 H3L parts and EuCl3Add the polytetrafluoroethylene (PTFE) of the DMF solvent containing certain volume
Guan Zhong, it is stirred at room temperature 20~40 minutes；
(2) this polyfluortetraethylene pipe is placed in stainless steel cauldron and sealed, be warming up to 120 DEG C of reaction 72h, drop naturally
Temperature, it is overnight to separate out colourless bulk crystals, wash, vacuum drying.
The H3L parts and EuCl3Mol ratio be preferably 1:1.5.
It is described that to be stirred at room temperature the time be preferably 30 minutes.
Advantages of the present invention and effect：
The Rare Earth Europium organic backbone complex of the present invention is to synthesize to obtain by the hot method of dimethylformamide, preparation side
Method is simple, and cost is low, and yield is high, and crystal mass is good.
Europium organic backbone complex provided by the invention is to be based on a kind of flexible ligand 5- (4 '-formic acid benzene oxygen) methylresorcinol
What dioctyl phthalate was constructed, the solid fluorescence emission spectrum of complex is shown under room temperature condition, when excitation wavelength is 395nm, is coordinated
Thing shows the stronger feux rouges features of Eu (III), and chromaticity coordinates is (0.5859,0.3178), and test shows its fluorescence quantum yield
For 93.0%, fluorescence lifetime 2.535ns.The europium organic backbone complex of the present invention may be used as optical material.
Brief description of the drawings
The crystal structure figure of europium organic backbone complex prepared by Fig. 1 embodiments 1.
X-ray powder diffraction figure (experiment and the theoretical mould of europium organic backbone complex prepared by Fig. 2 embodiments 1 in 298K
Intend figure).
Europium organic backbone complex and 5- (4 '-formic acid benzene oxygen) methylresorcinol dioctyl phthalate part prepared by Fig. 3 embodiments 1 exists
298K fluorescence spectra.
The feature feux rouges that europium organic backbone complex prepared by Fig. 4 embodiments 1 is sent under ultraviolet light.
The fluorescence decay curve of europium organic backbone complex prepared by Fig. 5 embodiments 1.
Embodiment
Embodiment 1
Weigh 0.1mmol H3L and 0.15mmolEuCl3Add in 15ml polyfluortetraethylene pipe, and add 5ml DMF,
It is stirred at room temperature 30 minutes.This polyfluortetraethylene pipe is sealed in stainless steel cauldron, controls temperature as 120 DEG C of heating 72h, from
So cooling, it is overnight to separate out colourless bulk crystals, wash, vacuum drying, the yield of gained europium organic backbone complex is 76%.
The structure determination of europium organic backbone complex：
The monocrystalline of suitable size is chosen under the microscope, by using X-ray diffraction, with Bruker Smart Apex II
Detector is 293K by the Mo-K alpha rays of graphite monochromator monochromatization, scan mode ω, the temperature for collecting data.It is all to spread out
Data are penetrated after SAINT is reduced, semiempirical absorption correction is carried out using SADABS programs.Crystal structure is direct by SHELXL-97
Method solves.Detailed axonometry data are shown in Table 1；Crystal structure is shown in Fig. 1, it is seen that each Eu (III) uses nine coordination modes,
With L3-It is coordinated using the pattern of chelating, bridging and chelating-bridging, is coordinated, be consequently formed three-dimensional netted using end group with DMF
Structure；X-ray powder diffraction as shown in Fig. 2 experimental diffraction collection of illustrative plates is consistent with the powder diffraction spectrum simulated according to crystal structure,
Show that crystal prototype thing is mutually homogeneous.
The crystallographic data of the complex of table 1
The luminosity of europium organic backbone complex：
The solid fluorescence emission spectrum (Fig. 3) of ligands and complexes is determined at room temperature.It is seen that
405nm wavelength excites down, and complex Eu (III) ions occurs due to f-f transition at 592nm, 617nm, 651nm, 695nm
Caused characteristic emission peak, Eu (III) ion is attributed to respectively5D0→7F1,5D0→7F2,5D0→7F3,5D0→7F4Feature
Transition.Eu (III) ion wherein at 617nm5D0→7F2Transition emission peak maximum intensity, illustrate part to the energy of rare earth ion
It is higher to measure transmission efficiency.By ultra violet lamp, it is observed that complex shows the stronger feux rouges features of Eu (III) (figure
4), chromaticity coordinates is (0.5859,0.3178).The fluorescence quantum yield and fluorescence lifetime of complex are tested, obtain fluorescence
Quantum yield is 93.0%, and fluorescence lifetime 2.535ns, fluorescence decay curve is shown in Fig. 5.
Embodiment 2
Weigh 0.1mmol H3L and 0.15mmolEuCl3Add in 15ml polyfluortetraethylene pipe, and add 5ml H2O,
It is stirred at room temperature 30 minutes.This polyfluortetraethylene pipe is sealed in stainless steel cauldron, after heating 72h at 120 DEG C, dropped naturally
Temperature, it is overnight to fail to separate out crystal, obtain a large amount of white powders.
Embodiment 3
Weigh 0.1mmol H3L and 0.15mmolEuCl3Add in 15ml polyfluortetraethylene pipe, and add 5ml volume ratios
For 1:1 H2O and DMF mixed solvent, it is stirred at room temperature 30 minutes.This polyfluortetraethylene pipe is sealed in stainless steel cauldron
In, after heating 72h at 120 DEG C, Temperature fall is overnight to separate out colourless bulk crystals, washs, vacuum drying, gained crystal compared with
Small, profile is poor, and yield is about 14%.
Embodiment 4
Weigh 0.1mmol H3L and 0.15mmolEuCl3Add in 15ml polyfluortetraethylene pipe, and add 5ml volume ratios
For 1:4 H2O and DMF mixed solvent, it is stirred at room temperature 30 minutes.This polyfluortetraethylene pipe is sealed in stainless steel cauldron
In, after heating 72h at 120 DEG C, Temperature fall is overnight to separate out colourless bulk crystals, washs, vacuum drying, gained crystal compared with
Good, yield is about 46%.
Claims (5)
1. a kind of europium organic backbone complex, it is characterised in that structural formula is：
2. a kind of preparation method of europium organic backbone complex as claimed in claim 1, it is characterised in that including following step
Suddenly：
(1) it is 1 by mol ratio:1~1.5 H3L parts and EuCl3Add the polyfluortetraethylene pipe of the DMF solvent containing certain volume
In, it is stirred at room temperature 20~40 minutes；
(2) this polyfluortetraethylene pipe is placed in stainless steel cauldron and sealed, be warming up to 120 DEG C reaction 72h, Temperature fall, every
Night separates out colourless bulk crystals, washs, vacuum drying.
A kind of 3. preparation method of europium organic backbone complex as claimed in claim 2, it is characterised in that the H3L parts with
EuCl3Mol ratio be 1:1.5.
4. a kind of preparation method of europium organic backbone complex as claimed in claim 2, it is characterised in that described to be stirred at room temperature
Time is 30 minutes.
A kind of 5. application of europium organic backbone complex as optical material as claimed in claim 1.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108484647A (en) * | 2018-04-17 | 2018-09-04 | 山西大学 | A kind of Nd complex and its preparation method and application |
| CN108586765A (en) * | 2018-05-04 | 2018-09-28 | 山西大学 | A kind of manganese Metal organic framework material and its preparation method and application |
-
2017
- 2017-07-12 CN CN201710564099.1A patent/CN107337688B/en active Active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108484647A (en) * | 2018-04-17 | 2018-09-04 | 山西大学 | A kind of Nd complex and its preparation method and application |
| CN108586765A (en) * | 2018-05-04 | 2018-09-28 | 山西大学 | A kind of manganese Metal organic framework material and its preparation method and application |
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