CN102532174A - Rare earth 2, 4, 6-tripyridyl triazine complex and preparation method thereof - Google Patents
Rare earth 2, 4, 6-tripyridyl triazine complex and preparation method thereof Download PDFInfo
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- CN102532174A CN102532174A CN2012100037952A CN201210003795A CN102532174A CN 102532174 A CN102532174 A CN 102532174A CN 2012100037952 A CN2012100037952 A CN 2012100037952A CN 201210003795 A CN201210003795 A CN 201210003795A CN 102532174 A CN102532174 A CN 102532174A
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Abstract
The invention discloses a rare earth organic light-emitting complex containing europium, terbium, samarium and 2, 4, 6-tripyridyl triazine and a preparation method thereof. The rare earth organic light-emitting complex is characterized in that a chemical formula of the rare earth organic light-emitting complex is LnxM2-x (TPTZ) L6 (C2H5OH).2H2O, wherein x is more than 0 and is less than or equal to 2; Ln is one of Sm3+, Eu3+ and Tb3; M is a rare earth ion which is different from the Ln; TPTZ is 2, 4, 6-tripyridyl triazine; and L is a negative monovalent inorganic anion. The rare earth organic light-emitting complex provided by the invention has the advantages of good stability, excellent dissolubility, long service life and high light-emitting efficiency. A polynuclear complex doped with a nonfluorescent or weakly-fluorescent rare earth ion provided by the invention is relatively low in price and higher in light-emitting efficiency. The preparation method has the advantages of simplicity in operation, mild condition, strong controllability, short treatment time and low energy consumption.
Description
Technical field
The present invention relates to a kind of organic light-emitting rare earth complexe and preparation method thereof, relate in particular to a kind of europium, terbium, samarium and 2,4, title complex of 6-TPTZ and preparation method thereof of containing.
Background technology
Rare earth organic complex is the luminescent material of one type of better performances owing to have good arrowband luminescent properties and long fluorescence lifetime, has obtained using widely at optical field.In addition because its luminous intensity is high, monochromaticity is good, so also be widely used in fields such as bioanalysis chemistry, laserable material, anti-false trademark, color shifting inks.
As one type of organic ligand commonly used, nitrogenous aromatic heterocycle is owing to absorb ultraviolet or visible luminous energy well, and can energy efficient shifted and pass to and its coordinate rare earth ion, thereby strengthens the luminous intensity of rare earth compounding.2,4, and 6-three pyridyl-1,3,5-triazines (2,4,6-tri (2-pyridyl)-1,3,5-triazine is called for short TPTZ) and have a plurality of aromatic nucleus, fine to the absorption of light, also can well pass ability.Simultaneously, this part has a plurality of nitrogen-atoms haptos, and ability and rare earth ion form five-ring, make title complex have special stability.
1969, people such as Durham synthesized 2,4 of lanthanon first in ethanolic soln, 6-TPTZ title complex [Ln (TPTZ) (NO
3)
3(H
2O)] 2H
2O (Ln=La-Nd, Sm-Lu, Y; Journal of Inorganic Nuclear Chemistry, 1969,31,571).People such as Zhiping Zheng had synthesized Eu (DBM) in 2004
3(TPTZ) ternary complex, and report that this title complex has stronger luminous intensity (Inorganica Chimica Acta, 2004,357,630).
2,4,6-three pyridyl-1,3,5-triazines has caused people's great interest as three teeth and bidentate ligand, and design forms polymer complex because it has suitable space.This special part has three haptos, according to the number that nitrogen-atoms is provided be divided into main, in, inferior three haptos, contain three nitrogen-atoms, two nitrogen-atoms and a nitrogen-atoms respectively.If rare earth ion RE
3+With the TPTZ mol ratio be 1: 1, then with main hapto coordination; RE
3+: TPTZ is 2: 1 o'clock, and then TPTZ is with main hapto and middle hapto and 2 rare-earth ion coordinations; If RE
3+: TPTZ is 1: 2, and then 2 TPTZ are all with main hapto and 1 rare-earth ion coordination.Therefore change the ratio and change anion ligand of TPTZ and rare earth ion, can form the title complex of different The Nomenclature Composition and Structure of Complexes.The mol ratio of existing report middle-weight rare earths ion and TPTZ is generally 1: 1, and Zhao Yongliang etc. are synthetic and studied RE (TPTZ)
2(ClO
4)
3(RE=Sm, Eu, Tb, luminosity Dy) (rare earth, 2008,29,86), the mol ratio of this type title complex middle-weight rare earths ion and TPTZ is 1: 2.
Summary of the invention
The shortcoming that the objective of the invention is to overcome prior art provides a kind of europium, terbium, samarium and 2,4, organic light-emitting rare earth complexe of 6-TPTZ and preparation method thereof of containing with not enough.The mol ratio that it is characterized in that rare earth ion and TPTZ is 2: 1, is that 1: 1 title complex is compared with the mol ratio of rare earth ion and TPTZ, and this type of title complex has stronger luminous intensity.Organic light-emitting rare earth complexe good stability provided by the invention, good, the long service life of solvability, luminous efficiency is high.The polynuclear coordination compound relative low price of non-fluorescence of doping provided by the invention or hypofluorescence rare earth ion, and luminous efficiency is higher.Preparing method of the present invention is easy and simple to handle, mild condition, and controllability is strong, and the treatment time is short, and energy expenditure is low.
The title complex of europium, terbium, samarium has stronger luminous intensity, but these three kinds of REEs cost an arm and a leg.In the title complex of europium, terbium, samarium, introduce a certain amount of cheap non-fluorescence or hypofluorescence rare earth ion (like La
3+, Gd
3+And Y
3+Deng), can significantly strengthen fluorescence activity rare earth ion (Eu
3+, Tb
3+, Sm
3+) luminous intensity, simultaneously can also reduce material cost.
When non-fluorescence or hypofluorescence rare earth ion or other metal ion mixing in title complex, give this ion with the part of these metallic ion coordination with the transmission ofenergy that absorbs.But because these ionic outermost electron layers are in full up, full sky or half-full steady state; Lowest excited attitude energy level is higher than the triplet energy level of part excited state far away; Make part can not energy efficient be passed to these ions; Be that energy is difficult for dissipating, pass to the luminescence rare earth ion and can only concentrate, thereby its luminous intensity is strengthened.So partly replace expensive Eu with cheap non-fluorescence or hypofluorescence rare earth ion or other metals ion
3+, Tb
3+, Sm
3+Ion not only can reduce the cost of luminescent material, and can also improve the luminous intensity of title complex.
The object of the invention is realized through following technical scheme:
A kind of europium, terbium, samarium and 2,4 of containing, the organic light-emitting rare earth complexe of 6-TPTZ, the chemical formula that it is characterized in that it is Ln
xM
2-x(TPTZ) L
6(C
2H
5OH) 2H
2O, 0＜x≤2 wherein, Ln is Sm
3+, Eu
3+, Tb
3+In a kind of, M is the rare earth ion different with Ln, L is negative univalent inorganic anion, TPTZ is 2,4, the 6-TPTZ, its structural formula is:
Described metal M ion is selected from La
3+, Ce
3+, Pr
3+, Nd
3+, Sm
3+, Eu
3+, Gd
3+, Tb
3+, Dy
3+, Ho
3+, Y
3+, Er
3+, Tm
3+, Yb
3+In one or more, and the metal M ion is different with the Ln ion.
Described negative univalent inorganic anion (L) is selected from Cl
-, Br
-, I
-, ClO
4 -, NO
3 -In one or more.
Especially, when x=2, the chemical formula of described organic light emission title complex is Ln
2(TPTZ) L
6(C
2H
5OH) 2H
2O.
Especially, when 0＜x＜2, described organic light emission title complex is adulterated title complex, and its chemical formula is Ln
xM
2-x(TPTZ) L
6(C
2H
5OH) 2H
2O.
A kind of preparation contains europium, terbium, samarium and 2,4, the organic light-emitting rare earth complexe Ln of 6-TPTZ
xM
2-x(TPTZ) L
6(C
2H
5OH) 2H
2The method of O may further comprise the steps:
(1) TPTZ is used anhydrous alcohol solution,, stir a certain amount of inorganic salt of rare earth LnL of adding down at 30-75 ℃
3With other inorganic salt of rare earth ML
3Ethanolic soln, regulate the pH value to 5-8, white precipitate, continued heated and stirred 0.5-24 hour, hold over night.
Wherein, the concentration of the ethanolic soln of described TPTZ is 0.001-1.0mol/L;
Wherein, described inorganic salt of rare earth LnL
3With other inorganic salt of rare earth ML
3Ethanolic soln middle-weight rare earths ion total mole number be the twice of TPTZ mole number;
Wherein, described temperature of reaction further is optimized for 40-70 ℃, and said pH value scope is optimized for 6-7, and the time of said continuation heated and stirred is 1-5 hour;
(2) mixture with step (1) gained filters, and filter cake is used absolute ethanol washing, and oven dry gets rare earth organic complex.
Description of drawings
Fig. 1 is Eu (the TPTZ) (NO of comparative example 1 preparation
3)
3(C
2H
5OH) H
2The fluorescent emission spectrogram of O.
Fig. 2 is the Eu of inventive embodiments 1 preparation
2(TPTZ) (NO
3)
6(C
2H
5OH) 2H
2The fluorescent emission spectrogram of O.
Fig. 3 is Tb (the TPTZ) (NO of comparative example 2 preparations
3)
3(C
2H
5OH) H
2The fluorescent emission spectrogram of O.
Fig. 4 is the Tb of inventive embodiments 2 preparations
2(TPTZ) (NO
3)
6(C
2H
5OH) 2H
2The fluorescent emission spectrogram of O.
Fig. 5 is the Eu of inventive embodiments 4 preparations
1.8Y
0.2(TPTZ) (NO
3)
6(C
2H
5OH) 2H
2The fluorescent emission spectrogram of O.
Fig. 6 is EuY (the TPTZ) (NO of inventive embodiments 5 preparations
3)
6(C
2H
5OH) 2H
2The fluorescent emission spectrogram of O.
Embodiment
Below in conjunction with accompanying drawing and specific embodiment the present invention is further described, but do not limit the present invention in any way.
The measuring method of complex fluorescent spectrum and fluorescence quantum yield: at room temperature; The pressed powder of title complex is measured its fluorescence spectrum with the FLS-920 XRF; Exciting and launching slit of europium, terbium, samarium complex is respectively 3nm, 1nm, 5nm, and excitation wavelength is respectively 362nm, 355nm, 370nm.Fluorescence quantum yield calculates according to fluorescence intensity, the fluorescence lifetime of title complex and gets (Journal of Fluorescence, 2009,19,641).
Comparative example 1
Take by weighing TPTZ 0.936g (3.0mmol), add the 30mL anhydrous alcohol solution, after 50 ℃ stirring was dissolved fully down, adding 30mL concentration was the Eu (NO of 0.1mol/L
3)
3Ethanol solution, the use mass concentration is 7% ammoniacal liquor adjust pH to 6.2, white precipitate occurs, continues stirring reaction 3 hours, hold over night.White solid after filtering, the white powder that obtains with the absolute ethanol washing after drying is Eu (TPTZ) (NO
3)
3(C
2H
5OH) H
2The O product.Its elementary composition analytical results is: experimental value (theoretical value), C%, 33.28 (33.63); H%, 2.91 (2.82); N%, 17.52 (17.65); Eu%, 21.28 (21.27).Fluorescence emission spectrum (Fig. 1) shows that this title complex shows as pure red emission, and the strongest emission wavelength is 615nm, and intensity is 9.3 * 10
3A.u..The fluorescence quantum yield of this title complex is 12.29%.
Embodiment 1
Take by weighing TPTZ 0.936g (3.0mmol), add the 30mL anhydrous alcohol solution, after 50 ℃ stirring was dissolved fully down, adding 60mL concentration was the Eu (NO of 0.1mol/L
3)
3Ethanol solution, the use mass concentration is 7% ammoniacal liquor adjust pH to 6.5, white precipitate occurs, continues stirring reaction 2 hours, hold over night.White solid after filtering, the white powder that obtains with the absolute ethanol washing after drying is Eu
2(TPTZ) (NO
3)
6(C
2H
5OH) 2H
2The O product.Its elementary composition analytical results is: experimental value (theoretical value), C%, 22.08 (22.44); H%, 2.22 (2.07); N%, 15.32 (15.70); Eu%, 28.32 (28.39).Fluorescence emission spectrum (Fig. 2) shows that this title complex shows as pure red emission, and the strongest emission wavelength is 616nm, and intensity is 7.0 * 10
4A.u..The fluorescence quantum yield of this title complex is 14.22%.
Comparative example 2
Take by weighing TPTZ 0.936g (3.0mmol), add the 30mL anhydrous alcohol solution, after 60 ℃ stirring was dissolved fully down, adding 30mL concentration was the Tb (NO of 0.1mol/L
3)
3Ethanol solution, the use mass concentration is 7% ammoniacal liquor adjust pH to 6.2, white precipitate occurs, continues stirring reaction 3 hours, hold over night.White solid after filtering, the white powder that obtains with the absolute ethanol washing after drying is Tb (TPTZ) (NO
3)
3(C
2H
5OH) H
2The O product.Its elementary composition analytical results is: experimental value (theoretical value), C%, 33.32 (33.30); H%, 2.63 (2.79); N%, 17.42 (17.48); Tb%, 22.12 (22.03).Fluorescence emission spectrum (Fig. 3) shows that this title complex shows as pure green emission, and the strongest emission wavelength is 542nm, and intensity is 2.4 * 10
4A.u..
Embodiment 2
Take by weighing TPTZ 0.936g (3.0mmol), add the 30mL anhydrous alcohol solution, after 60 ℃ stirring was dissolved fully down, adding 60mL concentration was the Tb (NO of 0.1mol/L
3)
3Ethanol solution, the use mass concentration is 7% ammoniacal liquor adjust pH to 6.5, white precipitate occurs, continues stirring reaction 2 hours, hold over night.White solid after filtering, the white powder that obtains with the absolute ethanol washing after drying is Tb
2(TPTZ) (NO
3)
6(C
2H
5OH) 2H
2The O product.Its elementary composition analytical results is: experimental value (theoretical value), C%, 22.24 (22.15); H%, 2.17 (2.05); N%, 15.39 (15.50); Tb%, 29.29 (29.31).Fluorescence emission spectrum (Fig. 4) shows that this title complex shows as pure green emission, and the strongest emission wavelength is 542nm, and intensity is 6.9 * 10
4A.u..
Comparative example 3
Take by weighing TPTZ 0.936g (3.0mmol), add the 30mL anhydrous alcohol solution, after 70 ℃ stirring was dissolved fully down, adding 30mL concentration was the Sm (NO of 0.1mol/L
3)
3Ethanol solution, the use mass concentration is 7% ammoniacal liquor adjust pH to 6.2, white precipitate occurs, continues stirring reaction 3 hours, hold over night.White solid after filtering, the white powder that obtains with the absolute ethanol washing after drying is Sm (TPTZ) (NO
3)
3(C
2H
5OH) H
2The O product.Its elementary composition analytical results is: experimental value (theoretical value), C%, 33.63 (33.70); H%, 2.55 (2.83); N%, 17.65 (17.69); Sm%, 21.00 (21.09).Fluorescence emission spectrum shows that the strongest emission wavelength of this title complex is 595nm, and intensity is 1.2 * 10
4A.u..
Embodiment 3
Take by weighing TPTZ 0.936g (3.0mmol), add the 30mL anhydrous alcohol solution, after 70 ℃ stirring was dissolved fully down, adding 60mL concentration was the Sm (NO of 0.1mol/L
3)
3Ethanol solution, the use mass concentration is 7% ammoniacal liquor adjust pH to 6.5, white precipitate occurs, continues stirring reaction 2 hours, hold over night.White solid after filtering, the white powder that obtains with the absolute ethanol washing after drying is Sm
2(TPTZ) (NO
3)
6(C
2H
5OH) 2H
2The O product.Its elementary composition analytical results is: experimental value (theoretical value), C%, 22.34 (22.51); H%, 2.20 (2.08); N%, 15.36 (15.75); Sm%, 28.31 (28.18).Fluorescence emission spectrum shows that the emission wavelength of this title complex is 595nm, and intensity is 4.0 * 10
4A.u..
Embodiment 4
Take by weighing TPTZ 0.936g (3.0mmol), add the 30mL anhydrous alcohol solution, after 55 ℃ stirring was dissolved fully down, adding 54mL concentration was the Eu (NO of 0.1mol/L
3)
3Ethanol solution and 6mL concentration are the Y (NO of 0.1mol/L
3)
3Ethanol solution, the use mass concentration is 7% ammoniacal liquor adjust pH to 6.5, white precipitate occurs, continues stirring reaction 2 hours, hold over night.White solid after filtering, the white powder that obtains with the absolute ethanol washing after drying is Eu
1.8Y
0.2(TPTZ) (NO
3)
6(C
2H
5OH) 2H
2The O product.Its elementary composition analytical results is: experimental value (theoretical value), C%, 22.14 (22.66); H%, 2.31 (2.09); N%, 15.42 (15.87); The mol ratio of Eu and Y is 8.65: 1 (theoretical value is 9: 1).Fluorescence emission spectrum (Fig. 5) shows that this title complex shows as pure red emission, and the strongest emission wavelength is 615nm, and intensity is 2.3 * 10
5A.u..The fluorescence quantum yield of this title complex is 14.71%.
Embodiment 5
Take by weighing TPTZ 0.936g (3.0mmol), add the 30mL anhydrous alcohol solution, after 55 ℃ stirring was dissolved fully down, adding 30mL concentration was the Eu (NO of 0.1mol/L
3)
3Ethanol solution and 30mL concentration are the Y (NO of 0.1mol/L
3)
3Ethanol solution, the use mass concentration is 7% ammoniacal liquor adjust pH to 6.5, white precipitate occurs, continues stirring reaction 2 hours, hold over night.White solid after filtering, the white powder that obtains with the absolute ethanol washing after drying is EuY (TPTZ) (NO
3)
6(C
2H
5OH) 2H
2The O product.Its elementary composition analytical results is: experimental value (theoretical value), C%, 23.58 (23.81); H%, 2.42 (2.20); N%, 16.55 (16.67); The mol ratio of Eu and Y is 1: 1.02 (theoretical value is 1: 1).Fluorescence emission spectrum (Fig. 6) shows that this title complex shows as pure red emission, and the strongest emission wavelength is 616nm, and intensity is 1.6 * 10
6A.u..The fluorescence quantum yield of this title complex is 17.28%.
Comparative examples and embodiment can find out; Europium, terbium, samarium and 2; 4; In the organic light-emitting rare earth complexe that the 6-TPTZ forms, the mol ratio of rare earth ion and TPTZ is that 2: 1 title complex is that 1: 1 title complex has stronger luminous intensity and higher fluorescence quantum yield than the mol ratio of corresponding rare earth ion and TPTZ.Mixing a certain proportion of non-fluorescence or hypofluorescence rare earth ion in the luminescent rare earth complexes can make title complex have stronger luminous intensity and higher fluorescence quantum yield.
Claims (9)
1. one kind contains europium, terbium, samarium and 2,4, the organic light-emitting rare earth complexe of 6-TPTZ, and the chemical formula that it is characterized in that it is Ln
xM
2-x(TPTZ) L
6(C
2H
5OH) 2H
2O, 0＜x≤2 wherein, Ln is Sm
3+, Eu
3+, Tb
3+In a kind of, M is the rare earth ion different with Ln, L is negative univalent inorganic anion, TPTZ is 2,4, the 6-TPTZ, its structural formula is:
2. one kind prepares and contains europium, terbium, samarium and 2,4, the organic light-emitting rare earth complexe Ln of 6-TPTZ
xM
2-x(TPTZ) L
6(C
2H
5OH) 2H
2The method of O may further comprise the steps:
(1) TPTZ is used anhydrous alcohol solution,, stir a certain amount of inorganic salt of rare earth LnL of adding down at 30-75 ℃
3With other inorganic salt of rare earth ML
3Ethanolic soln, regulate the pH value to 5-8, white precipitate, continued heated and stirred 0.5-24 hour, hold over night;
(2) mixture with step (1) gained filters, and filter cake is used absolute ethanol washing, and oven dry gets rare earth organic complex.
3. title complex as claimed in claim 1 is characterized in that, said metal M ion is selected from La
3+, Ce
3+, Pr
3+, Nd
3+, Sm
3+, Eu
3+, Gd
3+, Tb
3+, Dy
3+, Ho
3+, Y
3+, Er
3+, Tm
3+, Yb
3+In one or more, and the metal M ion is different with the Ln ion.
4. title complex as claimed in claim 1 is characterized in that, said negative univalent inorganic anion (L) is selected from Cl
-, Br
-, I
-, ClO
4 -, NO
3 -In one or more.
5. method as claimed in claim 2 is characterized in that, the concentration of the ethanolic soln of said TPTZ is 0.001-1.0mol/L.
6. method as claimed in claim 2 is characterized in that, said inorganic salt of rare earth LnL
3With other inorganic salt of rare earth ML
3Ethanolic soln middle-weight rare earths ion total mole number be the twice of TPTZ mole number.
7. method as claimed in claim 2 is characterized in that, said temperature of reaction can further be optimized for 40-70 ℃.
8. method as claimed in claim 2 is characterized in that, said pH value scope can further be optimized for 6-7.
9. method as claimed in claim 2 is characterized in that, the time of said continuation heated and stirred can further be optimized for 1-5 hour.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109867701A (en) * | 2017-12-01 | 2019-06-11 | 中国科学院大连化学物理研究所 | A kind of double triazine metal complexs of pyridyl group bridging and its preparation and application |
-
2012
- 2012-01-09 CN CN2012100037952A patent/CN102532174A/en active Pending
Non-Patent Citations (4)
| Title |
|---|
| 李海燕等: "2，4，6-三吡啶基三嗪-芳香羧酸镝配合物的合成及其荧光性能", 《发光学报》 * |
| 李海燕等: "掺杂卤代苯甲酸、含氮杂环铺配合物的合成、表征及荧光性能研究", 《稀土》 * |
| 赵艳芳等: "2, 4, 6- 三吡啶基三嗪稀土配合物的红外光谱和荧光性能", 《稀土》 * |
| 赵艳芳等: "稀土配合物RE( TPTZ)Cl3 的合成、表征及荧光性能研究", 《光谱学与光谱分析》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109867701A (en) * | 2017-12-01 | 2019-06-11 | 中国科学院大连化学物理研究所 | A kind of double triazine metal complexs of pyridyl group bridging and its preparation and application |
| CN109867701B (en) * | 2017-12-01 | 2021-07-20 | 中国科学院大连化学物理研究所 | Pyridyl bridged bistriazine metal complex and preparation and application thereof |
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Application publication date: 20120704 |