CN101302229A - Tetraheteropoly rare earth organic complex and preparation thereof - Google Patents

Tetraheteropoly rare earth organic complex and preparation thereof Download PDF

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CN101302229A
CN101302229A CNA2008101157090A CN200810115709A CN101302229A CN 101302229 A CN101302229 A CN 101302229A CN A2008101157090 A CNA2008101157090 A CN A2008101157090A CN 200810115709 A CN200810115709 A CN 200810115709A CN 101302229 A CN101302229 A CN 101302229A
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phen
hpa
rare earth
ethanolic soln
tta
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张敬畅
吕玉光
曹维良
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Beijing University of Chemical Technology
Hainan Institute of Science and Technology
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Beijing University of Chemical Technology
Hainan Institute of Science and Technology
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Abstract

The invention relates to quaternionic rare earth organic complexes as shown in general formula (I). The chemical name of the organic complexes is Eu-Tb thenoyltrifluoroacetone-N-phenylanthranilic acid-o-phenanthroline organic complexes. The chemical formula of the organic complexes is Tb1-xEux (TTA) 2 (N-HPA) Phen, wherein x is equal to 0-1. The invention also relates to a method for making the quaternionic rare earth organic complexes.

Description

A kind of Tetraheteropoly rare earth organic complex and preparation method thereof
Technical field
The present invention relates to the rare earth organic fluorescent materials technical field, be specifically related to Tetraheteropoly rare earth organic complex and synthetic method thereof.This Tetraheteropoly rare earth organic complex has photoluminescence and electroluminescent properties.
Background technology
Rare earth luminescent material can be divided into photoluminescence, cathodoluminescence, X ray is luminous and electroluminescent material etc., in fields such as laser, photoluminescence, electroluminescent title complexs bigger using value is arranged.
By the principle of luminosity of rare earth compounding as can be known, the structure of part and performance are the important factors that influences the rare earth compounding luminous efficiency, and design is synthetic, and to have a Novel Ligands of efficient sensitized luminescence most important.The bi-beta-diketo that contains many aromatic rings can absorb UV-light efficiently, easy again and rare earth coordination, thereby be a class ideal part.Experimental results demonstrate that adjacent Fei Luolin can significantly improve the luminous intensity of title complex as second part and rare-earth ion coordination, is a kind of extremely effectively " cooperated-sensitization agent ".This mainly contains the reason of two aspects: one, and as chromophore, it has very strong absorption in the ultraviolet region, and the energy level of its triplet excited state energy level and rare earth ion coupling, can give rare earth ion with transmission ofenergy effectively; Its two, the ligancy of rare earth ion is higher, binary complex generally all contains coordinated water, the electronic level of rare earth ion can with the high energy vibration energy state coupling of O-H oscillator, produce effective non-radiative deactivation, introduce the position that phenanthroline can tie up coordinated water.Therefore, the research of relevant rare earth phenanthroline ternary fluorescence complex both at home and abroad has a lot of reports, especially is the title complex of main part with beta-diketon.But also mainly concentrate on single beta-diketon, the luminescence studies of bi-beta-diketo, phenanthroline and rare earth ternary complexes.Compare with single beta-diketon, the bi-beta-diketo part can form dinuclear complex with rare earth ion because more hapto is arranged.This class title complex can be same double-core, also can be isodigeranyl nuclear, except the transmission ofenergy between part and the metal ion, also have the transmission ofenergy between metal ion, thereby luminous intensity is higher in isodigeranyl caryogamy compound.This class title complex also has the characteristics of easy gasification in addition, receives increasing concern in the research of photic, electroluminescent device.
At present the subject matter of the luminous Study on Complexes of rare earth beta-diketon be since thermostability, sublimability, the solvability of rare earth beta-diketon luminescent ligand compound self to have influenced the brightness applications scope of this type of photoluminescence and electroluminescent device narrower.
Document 1, Guo-Lun Zhong; Yong-Hong Wang, Chun-Kuan Wang.Assemblies ofluminescent organized molecular films based on the intermolecular energy transfer betweenrare earth complexes[J] Thin solid Films 385 (2001) 234-238. documents 2, Wang Cunkuan, Wang Yonghong, Zhong Guolun. rare earth compounding Gd (TTA) 3Two kinds of different effect [J] University Of Ningbo journal 2002,12 (4) of Phen: 49-51. document 1,2 has been introduced rare earth compounding Eu (TTA) 3Phen and Tb (TTA) 3The luminescent properties of Phen physical mixed, there is bigger difference in the characteristics of luminescence with pure europium, pure terbium coordination compound after discovery mixes, but photic not remarkable with electroluminescent intensity enhancing effect.
Document 3, Zhao Dongxu, Hong Ziruo, Liang Chunjun, et al.Enhancedelectroluminescence of europium (III) substitution in organic light emitting diodes[J] Thinsolid Films, 2000,363; 208. introduced europium and terbium double-core rare earth compounding Tb 1-xEu x(aas) 3The luminescent properties of Phen, there is bigger difference in the characteristics of luminescence of finding double-core rare earth compounding and pure europium, pure terbium coordination compound, in the terbium doped europium complex of rare earth ion, produces the fluorescence enhancement, photic remarkable with electroluminescent intensity enhancing effect, but it belongs to double-core ternary RE title complex.
Research about Tetraheteropoly rare earth organic complex yet there are no bibliographical information.
Summary of the invention
The preparation method who the purpose of this invention is to provide a kind of Tetraheteropoly rare earth organic complex and this Tetraheteropoly rare earth organic complex is provided.
The structural formula of Tetraheteropoly rare earth organic complex provided by the present invention is suc as formula shown in (I):
Figure A20081011570900041
In the formula (I): 1 be thenoyltrifluoroacetone (TTA), 2 for pyridyl anthranilic acid (N-HPA), 3 for phenanthroline (1,10-Phen);
The chemical name of formula (I) is: europium terbium thenoyltrifluoroacetone-pyridyl anthranilic acid-phenanthroline organic coordination compound, its chemical formula is: Tb 1-xEu x(TTA) 2(N-HPA) Phen, wherein x=0-1.
From structural formula (1) as can be seen the Tetraheteropoly rare earth organic complex symmetry be better than the ternary RE organic coordination compound, thermostability preferably, good processing characteristics are arranged.The simultaneously first part TTA, the second part N-HPA, the 3rd ligand 1,10-Phen and terbium ion can be the more effective europium ions that passes to of energy that absorbs, so have characteristics such as good conductivity, carrier transport are good.The rubescent look fluorescence of this quaternary europium complex has enlarged the rare earth organic complex range of application.
This Tetraheteropoly rare earth organic complex Tb 1-xEu x(TTA) 2(N-HPA) the concrete synthesis step of Phen is as follows:
A. press Eu (TTA) 2(N-HPA) Phen formula theory measurement is got EuCl respectively 3Ethanolic soln and/or TbCl 3Ethanolic soln, under agitation add 1, in the ethanolic soln of 10-Phen, in 50-80 ℃ of water-bath, slowly splash into the ethanolic soln of HTTA and the ethanolic soln of N-HPA while stirring; Make that the mol ratio of each component satisfies (EuCl in the system 3+ TbCl 3): 1,10-Phen: N-HPA: HTTA is 1: 1-4: 1-4: 2-8; Preferable mol ratio is 1: 1-2: 1-2: 2-4;
EuCl 3, TbCl 3, 1, the concentration of the ethanolic soln of 10-Phen, N-HPA, HTTA is 0.1～1.0mol.L -1, be respectively that these four kinds of compound dissolutions are formulated in ethanolic soln;
B. with the pH value of triethylamine regulating step A reaction soln to 6-7, produce white precipitate, room temperature leaves standstill 12～24h and makes its slaking, suction filtration is that 1: 1 aqueous ethanolic solution washs and is precipitated to no Cl with volume ratio -,, get white solid rare earth organic complex Tb 50～70 ℃ of oven dry 1-xEu x(TTA) 2(N-HPA) Phen.
The product that obtains has been carried out following sign:
1. differential thermal-thermogravimetric analysis (Fig. 1 .a differential thermal figure, b thermal multigraph), the endotherm(ic)peak of title complex about 250 ℃ do not followed weightless process, obviously be the crystal melting process of rare earth organic complex, as seen the fusing point of this rare earth organic complex is 250 ℃, shows that this title complex has better thermostability.
Examination of infrared spectrum (Fig. 2. wave-number range 400～4000cm -1), Tb 1-xEu x(TTA) 2(N-HPA) Phen title complex infrared spectra spectrogram shows: peak 1539cm -1Be 1,10-Phen-the N=C stretching vibration; 858cm -1, 721cm -1Be 1, the r of 10-Phen C-HStretching vibration; 1603 and 1511cm -1Be HT TA symmetry V C=OStretching vibration; 1577and1413cm -1. be N-HPA-COO -Symmetry V C=OStretching vibration, infrared spectra have proved its structure.
3. fluorescence spectrum (Fig. 3) behind the doping terbium, has enhancement to europium complex luminous.And the fluorescence enhancement has certain Changing Pattern.Promptly work as Tb 3+Molar fraction less than 0.25 o'clock, the complex fluorescent intensity level is with Tb 3+Increase and increase, work as Tb 3+Molar fraction equal at 0.5 o'clock, the fluorescence intensity level maximum.Work as Tb 3+Molar fraction greater than 0.5 o'clock, the organic coordination compound fluorescence intensity reduces gradually.Independent Tb 3+And Eu 3+Rare earth compounding fluorescence intensity a certain proportion of Tb that mixes 3+And Eu 3+A little less than the double-core rare earth compounding fluorescence intensity, Tb wherein 0.5Eu 0.5(TTA) 2(N-HPA) photoluminescence intensity of the novel title complex of Phen is better, and Tb is described 3+Be incorporated into Eu 3+Back photoluminescence has synergy.
Electroluminescent spectrum (Fig. 4. voltage 16V), the electroluminescent intensity that shows the title complex that the doping terbium is later mainly is the contribution of europium, terbium faint luminous less to the luminous intensity contribution, its effect only is that to strengthen the feature of europium luminous.Double-core rare earth compounding Tb 0.5Eu 0.5(TTA) 2(N-HPA) the Phen electroluminescent properties is better.The result shows that this is the good rare earth compounding of a class luminescent properties, has good DEVELOPMENT PROSPECT.
The invention has the beneficial effects as follows: synthesized Tetraheteropoly rare earth organic complex Tb with chemical synthesis 1-xEu x(TTA) 2(N-HPA) Phen.It is good that this title complex has solvability, solvable in organic solvents such as tetrahydrofuran (THF) and chloroform; Heat stability is good has good processing characteristics; Good conductivity, carrier transport is good; Its photoluminescence is red fluorescence, has mixed up behind the nanometer ZnS obviously characteristic such as enhancing of electroluminescent.The synthetic route that is adopted is simple and easy to do.
Description of drawings:
Fig. 1 is differential thermal-thermogravimetric analysis figure of embodiment 2, and wherein, a is that differential thermal figure, b are thermal multigraph
Fig. 2 is embodiment 3 infrared spectrograms, and its wave-number range is 400～4000cm -1
Fig. 3 is the fluorescence spectrum comparison diagram of three kinds of samples, and wherein a is the Eu (TTA) of the preparation of embodiment 1 2(N-HPA) Phen sample, b are the Tb of embodiment 2 preparations 0.25Eu 0.75(TTA) 2(N-HPA) Phen sample, c are the Tb of embodiment 3 preparations 0.5Eu 0.5(TTA) 2(N-HPA) Phen sample
Fig. 4 is the electroluminescent spectrum figure of embodiment 3, its test voltage 16V
Embodiment
Embodiment 1
A. press Eu (TTA) 2(N-HPA) Phen formula theory measurement is got 0.2mol.L respectively -1EuCl 3Ethanolic soln 10ml under agitation adds 0.2mol.L -11, in the mixing solutions of 10-Phen ethanolic soln 10ml, then in 60 ℃ of water-baths, under constantly stirring, slowly splashing into 0.2mol.L -1HTTA ethanolic soln 20ml and 0.2mol.L -1N-HPA ethanolic soln 10ml.
B. use triethylamine adjust pH to 7, produce white precipitate, room temperature leaves standstill above-mentioned reactant 24h, makes its slaking, and suction filtration is precipitated to no Cl with absolute ethanol washing -, in 70 ℃ of baking ovens, dry, get white solid rare earth organic complex Eu (TTA) 2(N-HPA) Phen.
Embodiment 2
A. press Tb 0.25Eu 0.75(TTA) 2(N-HPA) Phen formula theory measurement is got 0.75mol.L respectively -1EuCl 3And 0.25mol.L -1TbCl 3Ethanolic soln 5ml mixes, and under agitation adds 0.25mol.L -11,10-Phen ethanolic soln 10ml uses 62 ℃ of heating in water bath then, is slowly splashing into 0.25mol.L under constantly stirring -1HTTA ethanolic soln 20ml, 0.25mol.L -1N-HPA ethanolic soln 10ml.
B. use triethylamine adjust pH to 6.5, produce white precipitate.Room temperature leaves standstill above-mentioned reactant 20h, makes its slaking, and suction filtration is precipitated to no Cl with absolute ethanol washing -, in 62 ℃ of baking ovens, dry, get white solid rare earth organic complex Tb 0.25Eu 0.75(TTA) 2(N-HPA) Phen.
Embodiment 3
A. press Tb 0.5Eu 0.5(TTA) 2(N-HPA) Phen formula theory measurement is got 0.5mol.L respectively -1EuCl 3And 0.5mol.L -1TbCl 3Ethanolic soln 5ml mixes, and under agitation adds 0.25mol.L -11,10-Phen ethanolic soln 10ml uses 65 ℃ of heating in water bath then, is slowly splashing into 0.25mol.L under constantly stirring -1HTTA ethanolic soln 20ml, 0.25mol.L -1N-HPA ethanolic soln 10ml.
B. use triethylamine adjust pH to 6.6, produce white precipitate.Room temperature leaves standstill above-mentioned reactant 22h, makes its slaking, and suction filtration is precipitated to no Cl with absolute ethanol washing -, in 65 ℃ of baking ovens, dry, get white solid rare earth organic complex Tb 0.5Eu 0.5(TTA) 2(N-HPA) Phen.
Embodiment 4
A. press Tb 0.75Eu 0.25(TTA) 2(N-HPA) Phen formula theory measurement is got 0.25mol.L respectively -1EuCl 3And 0.75mol.L -1TbCl 3Ethanolic soln 5ml mixes, and under agitation adds 0.28mol.L -11,10-Phen ethanolic soln 10ml uses 70 ℃ of heating in water bath then, is slowly splashing into 0.28mol.L under constantly stirring -1HTTA ethanolic soln 20ml, 0.28mol.L -1N-HPA ethanolic soln 10ml.
B. use triethylamine adjust pH to 6.8, produce white precipitate.Room temperature leaves standstill above-mentioned reactant 23h, makes its slaking, and suction filtration is precipitated to no Cl with absolute ethanol washing -, in 68 ℃ of baking ovens, dry, get white solid rare earth organic complex Tb 0.75Eu 0.25(TTA) 2(N-HPA) Phen.
Embodiment 5
A. press Tb (TTA) 2(N-HPA) Phen formula theory measurement is got 0.2mol.L -1TbCl 3Ethanolic soln 10ml mixes, and under agitation adds 0.20mol.L -11,10-Phen ethanolic soln 10ml uses 70 ℃ of heating in water bath then, is slowly splashing into 0.20mol.L under constantly stirring -1HTTA ethanolic soln 20ml, 0.20mol.L -1N-HPA ethanolic soln 10ml.
B. use triethylamine adjust pH to 6.8, produce white precipitate.Room temperature leaves standstill above-mentioned reactant 25h, makes its slaking, and suction filtration is precipitated to no Cl with absolute ethanol washing -, in 68 ℃ of baking ovens, dry, get white solid rare earth organic complex Tb (TTA) 2(N-HPA) Phen.

Claims (3)

1. Tetraheteropoly rare earth organic complex, its structural formula is suc as formula shown in (I):
Figure A2008101157090002C1
In the formula (I): 1 be thenoyltrifluoroacetone (TTA), 2 for pyridyl anthranilic acid (N-HPA), 3 for adjacent luxuriant and rich with fragrance sound of vomiting quinoline (1,10-Phen);
The chemical name of formula (I) is: the luxuriant and rich with fragrance sound of vomiting of europium terbium thenoyltrifluoroacetone-pyridyl anthranilic acid-neighbour quinoline organic coordination compound, its chemical formula is: Tb 1-xEu x(TTA) 2(N-HPA) Phen, wherein x=0-1.
2. the preparation method of a Tetraheteropoly rare earth organic complex as claimed in claim 1, concrete steps are as follows:
A. press Eu (TTA) 2(N-HPA) Phen formula theory measurement is got EuCl respectively 3Ethanolic soln and/or TbCl 3Ethanolic soln, under agitation add 1, in the ethanolic soln of 10-Phen, in 50-80 ℃ of water-bath, slowly splash into the ethanolic soln of HTTA and the ethanolic soln of N-HPA while stirring;
Wherein the add-on of each component should satisfy (EuCl 3+ TbCl 3): 1, the mol ratio of 10-Phen: N-HPA: HTTA is 1: 1-4: 1-4: 2-8;
EuCl 3, TbCl 3, 1, the concentration of the ethanolic soln of 10-Phen, N-HPA, HTTA is 0.1～1.0mol.L -1, be respectively that these four kinds of compound dissolutions are formulated in ethanolic soln;
B. with the pH value of triethylamine regulating step A reaction soln to 6-7, produce white precipitate, room temperature leaves standstill 12～24h and makes its slaking, suction filtration is that 1: 1 aqueous ethanolic solution washs and is precipitated to no Cl with volume ratio -,, get white solid rare earth organic complex Tb 50～70 ℃ of oven dry 1-xEu x(TTA) 2(N-HPA) Phen.
3. the preparation method of Tetraheteropoly rare earth organic complex according to claim 2 is characterized in that (EuCl in the described reaction system of steps A 3+ TbCl 3): 1, the mol ratio of 10-Phen: N-HPA: HTTA is 1: 1-2: 1-2: 2-4.
CNA2008101157090A 2008-06-27 2008-06-27 Tetraheteropoly rare earth organic complex and preparation thereof Pending CN101302229A (en)

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CN101717629B (en) * 2009-07-06 2012-11-14 中国科学院长春光学精密机械与物理研究所 Optical oxygen sensing composite material and preparation method thereof
CN103739926A (en) * 2013-12-31 2014-04-23 杭州索康博能源科技有限公司 Fluorescent EVA (ethylene-vinyl acetate) glue film
CN103834383A (en) * 2014-03-20 2014-06-04 中国计量学院 Rare earth complex red fluorescent material and preparation method and application thereof
CN104004121A (en) * 2014-05-29 2014-08-27 常州大学 Method for preparing aromatic carboxylic acid macromolecular fluorescent rare-earth complex
CN107540846A (en) * 2017-07-14 2018-01-05 重庆师范大学 A kind of rare earth polymer fluorescent material and preparation method thereof
CN108642546A (en) * 2018-04-18 2018-10-12 华东师范大学 A kind of preparation method and application of rare earth nano piece fluorescence membrane sensor

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101717629B (en) * 2009-07-06 2012-11-14 中国科学院长春光学精密机械与物理研究所 Optical oxygen sensing composite material and preparation method thereof
CN102002062A (en) * 2010-09-26 2011-04-06 中科院广州化学有限公司 Polynuclear rare earth organic complex, and preparation method and application thereof
CN103739926A (en) * 2013-12-31 2014-04-23 杭州索康博能源科技有限公司 Fluorescent EVA (ethylene-vinyl acetate) glue film
CN103834383A (en) * 2014-03-20 2014-06-04 中国计量学院 Rare earth complex red fluorescent material and preparation method and application thereof
CN104004121A (en) * 2014-05-29 2014-08-27 常州大学 Method for preparing aromatic carboxylic acid macromolecular fluorescent rare-earth complex
CN107540846A (en) * 2017-07-14 2018-01-05 重庆师范大学 A kind of rare earth polymer fluorescent material and preparation method thereof
CN108642546A (en) * 2018-04-18 2018-10-12 华东师范大学 A kind of preparation method and application of rare earth nano piece fluorescence membrane sensor

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