CN103694266A - Hydrogen-bonded rare-earth metal europium complex fluorescent material and preparation method thereof - Google Patents

Hydrogen-bonded rare-earth metal europium complex fluorescent material and preparation method thereof Download PDF

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CN103694266A
CN103694266A CN201410001045.0A CN201410001045A CN103694266A CN 103694266 A CN103694266 A CN 103694266A CN 201410001045 A CN201410001045 A CN 201410001045A CN 103694266 A CN103694266 A CN 103694266A
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earth metal
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pyridine
europium
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陈建定
高勰
蔡梦军
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East China University of Science and Technology
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Abstract

The invention discloses a hydrogen-bonded rare-earth metal europium complex fluorescent material and a preparation method thereof. The hydrogen-bonded rare-earth metal europium complex is prepared from a proton transfer compound formed by a rare earth metal element europium and 2,6-diamido-pyridine and pyridine-2,6-dioctyl phthalate in a hydrogen bond coordination manner. The hydrogen-bonded rare-earth metal europium complex fluorescent material has the characteristics of narrow fluorescence emission peak, good monochromaticity, strong fluorescence intensity, good thermal stability and the like, and is an ideal red fluorescent material.

Description

A kind of hydrogen bond type rare-earth metal europium complex fluorescent material and preparation method thereof
Technical field
The present invention relates to a kind of hydrogen bond type rare-earth metal complexes and preparation method thereof, relate in particular to complex fluorescent material of a kind of Rare Earth Europium and preparation method thereof, belong to Rare Earth Functional Materials technical field.
Background technology
Rare earth luminescent material is especially noticeable in Rare Earth Functional Materials, the novel material of focus development during Ye Shi China " 12 ".It is good that the rare earth metal complex that adopts rare earth metal and the part with high specific absorbance to form has fluorescence monochromaticity, and luminous intensity high, is subject to people's attention day by day.
On the other hand, take molecule or ion as template, by hydrogen bond, molecule or ionic group being dressed up to the molecule aggregates with one or more dimensions structure is the important research content of the association areas such as supramolecular chemistry and crystal engineering.When rare earth ion and the self-assembly of hydrogen bond type supramolecule part, due to the synergy of hydrogen bond and part, can prepare the Rare Earth Functional Materials that performance is more excellent.
Chinese patent CN1618788A, CN101723962A, CN103254337A, CN102584871A, CN102633823A philosophy disclose with dinicotinic acid, 1,10-phenanthroline, dipyridyl, beta-diketon, Schiff's base are Rare Earth Functional Materials prepared by single part or mixed ligand, but in the molecular designing of rare earth compounding, do not relate to the self-assembly of hydrogen bond supramolecule.
Chinese patent CN101456875A discloses a class hydrogen bond type rare-earth metal complexes anti-biotic material, but does not provide structural information and the application in fluorescent material field of rare earth metal complex.
Several prototropy compound system and metal complexes thereof that carboxylic acid constructs as proton acceptor as proton donor and the amido of take of take in foreign literature, have been reported, such title complex is a kind of supramolecular system that contains hydrogen bond, there is diversified geometric configuration and topological framework, its metal complexes has novel fluorescence, magnetic and anti-microbial property, causes domestic and international scientific research personnel's extensive concern.As pyridine-2, the prototropy compound of 6-dioctyl phthalate and guanidine and with title complex (the A. Moghimi of cadmium metal Cd (II), S.Sheshmani, A. Shokrollahi, et al. Z. Anorg. Allg. Chem., 2004, 630, 617-624), 1, 10-phenanthroline-2, 9-dioctyl phthalate and 2, the prototropy compound of 6-diamino-pyridine and with title complex (the A. Moghimi of cobalt metal Co (II), R.Alizadeh, A. Shokrollahi, et al. Inorg. Chem., 2003, 42, 1616-1624), pyridine-2, 6-dioctyl phthalate and 2, the prototropy compound of 6-diamino-pyridine and with metallic cerium Ce (III), title complex (the S.Sheshmani of bismuth Bi (III), P.D.Kheirollahi, H.Aghabozorg ,et al. Z. Anorg. Allg. Chem., 2005,631,3058-3065), but in document, only relate to the structure of hydrogen related of bonding metal complexes, do not relate to it as a kind of application and research of new function material.On the other hand, pyridine-2,6-dioctyl phthalate and 2, the prototropy compound that 6-diamino-pyridine is constructed has larger conjugated structure, its specific absorbance is higher, can by organic ligand ultraviolet-visible district excite and part transmits excitation rare-earth ion to the useful energy of rare earth ion and sends characteristic fluorescence, and luminous monochromaticity and stability better.
Summary of the invention
The object of the invention is to synthetic a kind of hydrogen bond type rare-earth metal europium complex with network topology structure, to obtaining the rare-earth luminescent material that fluorescence emission peak is narrow, monochromaticity good, intensity is high and thermal stability is good.
A kind of hydrogen bond type rare-earth metal europium complex of the present invention, its chemical constitution is:
Eu(pydaH) 2(pydc) 3·H 5O 2·2H 2O
In formula, Eu is Rare Earth Europium element; PydaH is protonated DAP; Pydc is pyridine-2, the dianion of 6-dioctyl phthalate; H 5o 2be two oxonium ions, separately can be expressed as [H (H 2o) 2] +; Its structure is Fig. 1.
The preparation method of hydrogen bond type rare-earth metal europium complex of the present invention, is characterized in that, comprises the following steps:
(1) Rare Earth Europium salt is dissolved in water, ethanol or its mixing solutions, obtains rare earth ion solution A; Wherein, in mixing solutions, the volume ratio of water and ethanol is 0:1～1:0; The ionic concn of Rare Earth Europium salt in solution is 0.01～0.2 molL -1;
Described rare-earth europium salt is selected from one or more mixtures in the muriate, oxalate, nitrate of europium, preferably europium nitrate;
(2) by DAP and pyridine-2,6-dioctyl phthalate is dissolved in water, ethanol or its mixing solutions, and wherein, in mixing solutions, the volume ratio of water and ethanol is 0:1～1:0; DAP and pyridine-2, the mol ratio of 6-dioctyl phthalate is 1:0.95～1:1.05; The volumetric molar concentration of DAP in water, ethanol or its mixing solutions is 0.02～0.2 molL -1; Above-mentioned solution, after 50～80 ℃ of reaction 12～24 h, filters, and washing, is placed in 50～70 ℃ of vacuum-drying 4～6 h by filter residue, obtains prototropy compd B;
(3) prototropy compd B is dissolved in water, ethanol or its mixing solutions, obtains prototropy compd B solution; Wherein, in mixing solutions, the volume ratio of water and ethanol is 1:0～1:5; The volumetric molar concentration of prototropy compd B in solution is 0.02～0.2 molL -1;
(4) above-mentioned prototropy compd B solution is warming up to 50～80 ℃, dropwise adds rare earth ion solution A, until the mol ratio of mixing solutions Rare Earth Metal Ions and prototropy compd B is 1:1～1:3; After stirring reaction 4～6 h, filter, filter residue is placed in to 50～70 ℃ of vacuum-drying 4～6 h, filtrate is placed in slowly crystallization under room temperature, obtains faint yellow bulk crystals, is hydrogen bond type rare-earth metal europium complex C.
The quantitative analysis of described hydrogen bond type rare-earth metal complexes C, H, N, O element adopts elemental analyser to measure.
The modular construction of described hydrogen bond type rare-earth metal europium complex and space packed structures adopt X-ray single crystal diffractometer to measure.
The solid fluorescence performance of described hydrogen bond type rare-earth metal europium complex adopts fluorescence spectrophotometer to measure.
The thermostability of described hydrogen bond type rare-earth metal europium complex adopts thermogravimetric analyzer to measure, N 2atmosphere, 10 ℃/min of heat-up rate, temperature range: room temperature to 800 ℃.
X-ray single crystal diffraction Measurement results is: the amino in DAP, protonated hydrogen, oxonium ion, water molecules, pyridine-2, the carboxyl of 6-dioctyl phthalate has been constructed title complex Eu (pydaH) jointly by hydrogen bond self-assembly effect 2(pydc) 3h 5o 22H 2the network topology structure of O crystal.
Solid fluorescence Measurement results is: the maximum excitation wavelength of hydrogen bond type rare-earth metal europium complex is 395 nm, under the exciting of maximum excitation wavelength, the characteristic fluorescence of the europium that title complex is launched at 579 nm, 590 nm, 613 nm, 649 nm, 692 nm places belongs to respectively 5d 0→ 7f j(j=0～4) transition, wherein the strongest at the fluorescence emission peak at 590 nm places and 613 nm places, be red fluorescence, and fluorescence emission peak is narrow, monochromaticity is good, intensity is high.
Thermal weight loss Measurement results is: hydrogen bond type rare-earth metal europium complex is 200 ℃ of weightlessness (weightlessness that the weightlessness before 200 ℃ is crystal water) that just start above title complex main body, and resistance toheat is good.
The present invention designs synthetic hydrogen bond type rare-earth metal europium complex by special molecular structure can launch red fluorescence under ultraviolet excitation, and emission peak is narrow, monochromaticity is good, fluorescence intensity is high, its main thermal weight loss temperature is more than 200 ℃, is a kind of thermally-stabilised, Rare Earth Functional Materials that fluorescence property is good.
Accompanying drawing explanation
Fig. 1 is title complex Eu (pydaH) 2(pydc) 3h 5o 22H 2the molecular structure ellipsoid figure of O
Fig. 2 is title complex Eu (pydaH) 2(pydc) 3h 5o 22H 2the hydrogen bond self assembled three-dimensional accumulation graph of O
Fig. 3 is title complex Eu (pydaH) 2(pydc) 3h 5o 22H 2o is along the hydrogen bond self-assembly accumulation graph of b axle
Fig. 4 is title complex Eu (pydaH) 2(pydc) 3h 5o 22H 2o is usingd 615 nm as the solid fluorescence excitation spectrum of monitoring wavelength
Fig. 5 is title complex Eu (pydaH) 2(pydc) 3h 5o 22H 2the solid fluorescence emmission spectrum that O locates at maximum excitation wavelength (395 nm)
Fig. 6 is title complex Eu (pydaH) 2(pydc) 3h 5o 22H 2the thermogravimetric curve of O.
Embodiment
Embodiment 1
Take the Eu (NO of 0.2676 g (0.6 mmol) 3) 36H 2o is dissolved in 50 mL water, obtains solution A 1; Take 0.2183 g (2 mmol) 2,6-diamino-pyridine and 0.3342g (2 mmol) pyridine-2,6-dioctyl phthalate is dissolved in respectively in 100 mL ethanolic solns, 60 ℃ of stirring and refluxing are reacted 24 h, suction filtration, use washing with alcohol three times, 60 ℃ of vacuum-drying 4 h, obtain 0.4326 g (pydaH again 2) (pydc) prototropy compound B-11, productive rate 78.3%;
Take 0.3315 g (1.2 mmol) B1 and be dissolved in 30 mL water, obtain B1 solution; Be warming up to 80 ℃, A1 solution is dropwise added in B1 solution, after stirring reaction 5 h, filter, use washing with alcohol three times, 60 ℃ of dry 4 h, obtain 0.2212 g pale solid powder, productive rate 41.4%; Filtrate is placed in to slowly crystallization under room temperature, obtains faint yellow bulk crystals C1.By a small amount of water and washing with alcohol three times for C1, filter, obtain being suitable for the title complex of X-ray single crystal diffraction.
Embodiment 2
Take the EuCl of 0.3664 g (1 mmol) 36H 2o is dissolved in 5 mL ethanol, obtains solution A 2; Take 0.2728 g (2.5 mmol) 2,6-diamino-pyridine and 0.4345 g (2.6 mmol) pyridine-2,6-dioctyl phthalate is dissolved in respectively in 15 mL water, 70 ℃ of stirring and refluxing are reacted 12 h, suction filtration, wash with water three times, 50 ℃ of vacuum-drying 6 h, obtain 0.6451 g (pydaH again 2) (pydc) prototropy compd B 2, productive rate 91.2%;
Take 0.3315 g (1.2 mmol) B2 and be dissolved in the mixed solvent of 10 mL water and 50mL ethanol, obtain B2 solution; Be warming up to 50 ℃, A2 solution is dropwise added in B2 solution, stirring reaction 6 h, filter, and use washing with alcohol three times, and 50 ℃ of dry 5 h, obtain 0.2885 g pale solid powder, productive rate 48.9%; Filtrate is placed in to slowly crystallization under room temperature, obtains faint yellow bulk crystals C2.By a small amount of water and washing with alcohol three times for C2, filter, obtain being suitable for the title complex of X-ray single crystal diffraction.
Embodiment 3
Take the Eu of 0.3380 g (0.5 mmol) 2(C 2o 4) 36H 2o is dissolved in 10 mL water and 10mL alcohol mixed solvent, obtains solution A 3; Take 0.5238 g (4.8 mmol) 2,6-diamino-pyridine and 0.7688 g (4.6 mmol) pyridine-2,6-dioctyl phthalate is dissolved in respectively in 40 mL ethanolic solns, 50 ℃ of stirring and refluxing are reacted 20 h, suction filtration, by washing with alcohol three times, 70 ℃ of vacuum-drying 4 h, obtain 1.1737 g (pydaH 2) (pydc) prototropy compd B 3, productive rate 90.8%;
Take 0.8288 g (3 mmol) B3 and be dissolved in the mixing solutions of 10 mL water and 5 mL ethanol, obtain B3 solution; Be warming up to 50 ℃, A3 solution is dropwise added in B3 solution, stirring reaction 4 h, filter, and use absolute ethanol washing three times, and 60 ℃ of dry 4 h, obtain 0.5787 g pale solid powder, productive rate 52.0%; Filtrate is placed in to slowly crystallization under room temperature, obtains faint yellow bulk crystals C3.By a small amount of water and washing with alcohol three times for C3, filter, obtain being suitable for the title complex of X-ray single crystal diffraction.
Embodiment 4
Complex crystal C1, C2 in embodiment 1～3, C3 all adopt Vario EL III type elemental analyser to measure C, H, N, O content, and data are listed in table 1.
Table 1 ultimate analysis data
Figure 2014100010450100002DEST_PATH_IMAGE001
The complex crystal C1 getting in embodiment 1 adopts Bruker SMART-CCD type X-ray single crystal diffractometer to carry out the test of X-ray single crystal diffraction, and it the results are shown in table 2～table 3 and Fig. 1～Fig. 3.
X-ray single crystal diffraction Measurement results is: the molecular formula of hydrogen bond type rare-earth metal complexes C1 is C 31h 34n 9o 16eu, chemical constitution is Eu (pydaH) 2(pydc) 3h 5o 22H 2o.Title complex belongs to oblique system, P2/c spacer, unit cell parameters a=9.673 (3), b=10.656 (3), c=19.825 (5), α=90 °, β=114.886 (11) °, γ=90 °, crystalline size is 0.21 mm * 0.14, mm * 0.20 mm, V=1853.7 (9) 3, Z=2, D c=1.685 g/cm 3, μ=1.777 mm -1, F (000)=948, R 1=0.0166, wR 2=0.0438, GOF=1.126.Fig. 1 shows, in structural unit, europium Eu (III) adopts nine coordinations, be positioned at crystallographic system symmetry axis center, each europium ion and three pyridine-2 in the minimal structure unit of crystal, two carboxylate radicals in 6-dioctyl phthalate molecule and the nitrogen-atoms coordination on pyridine ring, and form respectively two five-rings on limits altogether.A hydrogen proton and two water molecules actings in conjunction have formed [H (H 2o) 2] +ion (Eigen ion), but do not form coordination with central ion.Fig. 2 and Fig. 3 show, the amino in DAP, protonated hydrogen, oxonium ion, water molecules, pyridine-2, and the carboxyl of 6-dioctyl phthalate has been constructed title complex Eu (pydaH) jointly by hydrogen bond self-assembly effect 2(pydc) 3h 5o 22H 2the network topology structure of O crystal.
Table 2 title complex Eu (pydaH) 2(pydc) 3h 5o 22H 2selectivity bond distance's () of O and bond angle (°)
Figure 2014100010450100002DEST_PATH_IMAGE003
The symmetry transformation of equivalent atom: #1-x+1, y ,-z+1/2.
Table 3 title complex Eu (pydaH) 2(pydc) 3h 5o 22H 2the hydrogen bond of O
The symmetry transformation of equivalent atom: #1-x+1, y ,-z+1/2, #2-x+2 ,-y+1 ,-z+1, #3-x+1 ,-y ,-z+1, #4 x+1 ,-y, z+1/2, #5-x, y ,-z+1/2, #6-x ,-y+1 ,-z.
The complex crystal C1 getting in embodiment 1 adopts Fluorolog-3-P type ultraviolet-visible-near-infrared fluorescent spectrograph to carry out solid fluorescence test, and its result is Fig. 4 and Fig. 5.
The complex crystal C1 getting in embodiment 1 adopts STA 409 PC/PG type thermogravimetric analyzers to carry out heat stability testing, and its thermogravimetric curve is Fig. 6.

Claims (4)

1. a hydrogen bond type rare-earth metal europium complex, its chemical constitution is:
Eu(pydaH) 2(pydc) 3·H 5O 2·2H 2O
In formula, Eu is Rare Earth Europium element; PydaH is protonated DAP; Pydc is pyridine-2, the dianion of 6-dioctyl phthalate; H 5o 2be two oxonium ions, separately can be expressed as [H (H 2o) 2] +.
2. hydrogen bond type rare-earth metal europium complex according to claim 1, it is characterized in that, each europium ion and three pyridine-2 in crystalline structure unit, two carboxylate radicals in 6-dioctyl phthalate molecule and the nitrogen-atoms on pyridine ring form nine tooth coordinations, 2, amino in 6-diamino-pyridine, protonated hydrogen, oxonium ion, water molecules, pyridine-2, the network topology structure that the carboxyl of 6-dioctyl phthalate is constructed complex crystal jointly by hydrogen bond self-assembly effect.
3. the preparation method of hydrogen bond type rare-earth metal europium complex according to claim 1, is characterized in that, comprises the following steps:
(1) Rare Earth Europium salt is dissolved in water, ethanol or its mixing solutions, obtains rare earth ion solution A; Wherein, in mixing solutions, the volume ratio of water and ethanol is 0:1～1:0; The ionic concn of Rare Earth Europium salt in solution is 0.01～0.2 molL -1;
Described rare-earth europium salt is selected from one or more mixtures in the muriate, oxalate, nitrate of europium;
?(2) by DAP and pyridine-2,6-dioctyl phthalate is dissolved in water, ethanol or its mixing solutions, and wherein, in mixing solutions, the volume ratio of water and ethanol is 0:1～1:0; DAP and pyridine-2, the mol ratio of 6-dioctyl phthalate is 1:0.95～1:1.05; The volumetric molar concentration of DAP in water, ethanol or its mixing solutions is 0.02～0.2 molL -1; Above-mentioned solution, after 50～80 ℃ of reaction 12～24 h, filters, and washing, is placed in 50～70 ℃ of vacuum-drying 4～6 h by filter residue, obtains prototropy compd B;
(3) prototropy compd B is dissolved in water, ethanol or its mixing solutions, obtains prototropy compd B solution; Wherein, in mixing solutions, the volume ratio of water and ethanol is 1:0～1:5; The volumetric molar concentration of prototropy compd B in solution is 0.02～0.2 molL -1;
(4) above-mentioned prototropy compd B solution is warming up to 50～80 ℃, dropwise adds rare earth ion solution A, until the mol ratio of mixing solutions Rare Earth Metal Ions and prototropy compd B is 1:1～1:3; After stirring reaction 4～6 h, filter, filter residue is placed in to 50～70 ℃ of vacuum-drying 4～6 h, filtrate is placed in slowly crystallization under room temperature, obtains faint yellow bulk crystals, is hydrogen bond type rare-earth metal europium complex C.
4. hydrogen bond type rare-earth metal europium complex according to claim 1, is characterized in that, it possesses fluorescence property, under ultraviolet excitation, and transmitting red fluorescence.
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CN103992341A (en) * 2014-05-30 2014-08-20 天津师范大学 Mixed organic carboxylic acid containing rare earth complex as well as preparation method and application of mixed organic carboxylic acid containing rare earth complex
CN104817578A (en) * 2015-03-18 2015-08-05 天津师范大学 Rare earth metal complex based on 1, 4-naphthalic acid ligand, preparation method and application thereof
CN105837830A (en) * 2016-04-19 2016-08-10 大连理工大学 Preparation method and application of europium coordination polymer for visible detection on p-nitrophenol and iron ion
CN112625255A (en) * 2019-11-28 2021-04-09 福建农林大学 Synthetic method and application of proportional fluorescent probe for quantitatively detecting hypochlorite ions
CN113234229A (en) * 2021-04-21 2021-08-10 陕西科技大学 Ionic hydrogen bond organic framework material and preparation method and application thereof

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CN113234229A (en) * 2021-04-21 2021-08-10 陕西科技大学 Ionic hydrogen bond organic framework material and preparation method and application thereof

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