CN101914108B - 4-amino-3,5-bi(2-pyridyl)-1,2,4-triazole-silver (I) complex and preparation method thereof - Google Patents
4-amino-3,5-bi(2-pyridyl)-1,2,4-triazole-silver (I) complex and preparation method thereof Download PDFInfo
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- CN101914108B CN101914108B CN2010102710153A CN201010271015A CN101914108B CN 101914108 B CN101914108 B CN 101914108B CN 2010102710153 A CN2010102710153 A CN 2010102710153A CN 201010271015 A CN201010271015 A CN 201010271015A CN 101914108 B CN101914108 B CN 101914108B
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Abstract
The invention relates to a 4-amino-3,5-bi(2-pyridyl)-1,2,4-triazole-silver (I) complex and a preparation method thereof. The chemical formula of the complex is ([AgL](NO3))infinity, wherein L is 4-amino-3,5-bi(2-pyridyl)-1,2,4-triazole. The preparation method of the complex comprises the step of synthesizing the compound by adopting AgNO3 and 4-amino-3,5-bi(2-pyridyl)-1,2,4-triazole (L) as reaction raw materials through three methods of a layered diffusion method, a solvent volatilization method and a low-temperature hydrothermal method, wherein the yield of the complex prepared by the solvent volatilization method is higher; and the complex has the advantages of good heat stability, simple synthesis, convenient operation, good reproducibility and the like. The obtained complex crystals can be further researched and applied to the field of crystallized fluorescent materials.
Description
Technical field
The present invention is specifically related to d
10A kind of 4-amino-3 in metal complex fluorescent material field, two (the 2-pyridyl)-1,2 of 5-, 4-triazole-Yin (I) title complex and preparation method thereof.
Background technology
In recent years, ligand polymer is owing to the hot subject that becomes in the performance of aspects such as molecule (ion) identification and exchange, absorption, selectivity catalysis, optics and magneticsubstance and potential using value thereof in the inorganic chemistry research, and presents the impetus of fast development.In ligand polymer, metal ion links together part and makes their arrangement have clear and definite directive property, so just part may be lined up according to the mode of imagining in advance, thus the new compound that acquisition has expected structure and specific function.And one of design and the topmost purpose of synthetic ligand polymer are exactly to control the structure and the performance of final product by the structural unit of design in advance, to satisfy people's particular demands.
Nitrogen heterocyclic ring class polydentate ligand has a plurality of haptos and stronger coordination ability, can form the ligand polymer with various dimensions and structure with metallic ion coordination the time.In addition, this type of part is as nitrogenous aroma system, in the assembling process of corresponding title complex, easily form π ... pi accumulation and C-H ... weak interactions such as π, its N atom also might form hydrogen bond simultaneously, thereby assembles out many supramolecular aggregations with novel structure and specific function.In addition, the formed title complex of nitrogen heterocyclic ring class part also has good light, electricity, magnetic, catalysis, fractionation by adsorption and biological activity etc., is also showing the potential prospect aspect the application and development of associated materials, so receive people's very big concern all the time.4-amino-3, two (the 2-pyridyl)-1 of 5-, 2, the 4-triazole is typical nitrogen heterocyclic ring part, has good conjugacy, proton acceptability and coordination selectivity etc., is easy to form the super molecular compound with one dimension, two dimension, three-dimensional net structure with metal and compares with other transition metal ion, 4-amino-3, two (the 2-pyridyl)-1,2 of 5-, also nobody the silver of 4-triazole (I) title complex report for work so far.
Summary of the invention
The objective of the invention is to propose a kind of 4-amino-3, two (the 2-pyridyl)-1,2 of 5-, 4-triazole-Yin (I) title complex and preparation method thereof, this title complex Heat stability is good, and preparation technology is simple and easy to operate, the productive rate height, good reproducibility, thus overcome deficiency of the prior art.
For achieving the above object, the present invention has adopted following technical scheme:
A kind of 4-amino-3 that contains, two (the 2-pyridyl)-1,2 of 5-, the silver of 4-triazole (I) title complex, it is characterized in that: described title complex has following chemical formula, that is: { [AgL] (NO
3)
∞, wherein L is a 4-amino-3, two (the 2-pyridyl)-1,2 of 5-, and the 4-triazole, skeleton symbol is as follows:
Say further: described complex crystal belongs to rhombic system, and spacer is P2
12
12
1, unit cell parameters is
α=90 °, β=90 °, γ=90 °,
Described title complex is by the positively charged ion unit [Ag (L)] of one dimension spiral chain-like structure
+And NO
3 -Negatively charged ion is formed, wherein Ag
IBe the tetrahedral coordination environment of distortion, the positively charged ion unit is parallel accumulation along the b direction of principal axis simultaneously, forms the passage that extends.
A kind of 4-amino-3 that contains, two (the 2-pyridyl)-1,2 of 5-, the preparation method of the silver of 4-triazole (I) title complex is characterized in that this method comprises the steps: under the room temperature AgNO
3Water-soluble formation bottom solution; Secondly adding above bottom solution mainly by volume ratio is that 1: 1 first alcohol and water mixes the buffer layer that forms, and interpolation contains 0.01molL above buffer layer thereafter
-1The methanol solution of part, form layering diffusion reaction system, with this layering diffusion reaction system lucifuge sealing and standing 10 days, colourless bulk-shaped monocrystal appears the boundary place of connecing of solution interface at the middle and upper levels to layering diffusion reaction system, this monocrystalline is separated, through washing, drying treatment, obtain target product successively.
A kind of 4-amino-3 that contains, two (the 2-pyridyl)-1,2 of 5-, the preparation method of the silver of 4-triazole (I) title complex is characterized in that this method is: under the room temperature with AgNO
3Water-soluble formation concentration is 0.02～0.06molL
-1Silver salt solution, simultaneously L is dissolved in methyl alcohol and forms ligand solution, concentration is 0.01～0.03molL
-1, then silver salt solution and ligand solution are directly mixed ligand L and AgNO in the reaction system
3Mol ratio be 1: 1～1: 2.Filter reaction mixture leaves standstill volatilization with filtrate, colourless bulk-shaped monocrystal occurs to filtrate, and this monocrystalline is separated, and through washing, drying treatment, obtains target product successively.
A kind of 4-amino-3 that contains, two (the 2-pyridyl)-1,2 of 5-, the preparation method of the silver of 4-triazole (I) title complex is characterized in that this method is: at room temperature with 0.1mmol AgNO
3And 0.05mmolL
-1Ligand L is soluble in water and mix, again with reaction mixture per hour 10 ℃ be heated to 60 ℃, kept this temperature 3 days, reduce to room temperature then, can obtain colourless bulk crystals this monocrystalline is separated, through washing, drying treatment, obtain target product successively.
The present invention adopts AgNO
3With L as reaction raw materials, and prepare the novel 4-amino-3 that contains by layering diffusion process, solvent evaporation method and hydrothermal reaction at low temperature respectively, two (the 2-pyridyl)-1 of 5-, 2, the silver of 4-triazole (I) title complex, its technology has simply, advantages such as easy to operate and reproducibility is good, especially wherein solvent flashing method also has the productive rate about 80%, and prepared title complex Heat stability is good is expected to obtain further research and development application in the fluorescent material field.
Description of drawings
Fig. 1 is a gained 4-amino-3 among the embodiment 1～9, two (the 2-pyridyl)-1,2 of 5-, the coordination environment figure of Ag (I) in the silver of 4-triazole (I) title complex;
Fig. 2 is a gained 4-amino-3 among the embodiment 1～9, two (the 2-pyridyl)-1,2 of 5-, the one dimension spiral-link composition of the silver of 4-triazole (I) title complex;
Fig. 3 is a gained 4-amino-3 among the embodiment 1～9, two (the 2-pyridyl)-1,2 of 5-, the three-dimensional accumulation graph of the silver of 4-triazole (I) title complex;
Fig. 4 is a gained 4-amino-3 among the embodiment 1～9, two (the 2-pyridyl)-1,2 of 5-, the solid state fluorescence spectrogram of the silver of 4-triazole (I) title complex;
Fig. 5 is a gained 4-amino-3 among the embodiment 1～9, two (the 2-pyridyl)-1,2 of 5-, the experiment of the X-ray powder diffraction (XPRD) of the silver of 4-triazole (I) title complex and theoretical contrast figure;
Fig. 6 is a gained 4-amino-3 among the embodiment 1～9, two (the 2-pyridyl)-1,2 of 5-, the thermogravimetric analysis graphic representation of the silver of 4-triazole (I) title complex.
Embodiment
This contains 4-amino-3 embodiment 1, two (the 2-pyridyl)-1,2 of 5-, and the preparation method of the silver of 4-triazole (I) title complex is:
Under the room temperature, with 0.05mmol AgNO
3Place the test tube bottom, use the 5mL dissolved in distilled water; Middle methyl alcohol and 1: 1 the mixing solutions 16mL of water volume ratio of adding; 0.05mmolL
-1Ligand L 5mL dissolve with methanol places the test tube upper strata; The lucifuge sealing and standing is 10 days then, and colourless bulk-shaped monocrystal appears in the place, boundary that connects of solution interface on the test tube wall.Crystal is used distilled water and washing with alcohol successively, and vacuum-drying is target product, and its productive rate is about 65%.The main infrared absorption peak of this target product is: 1631w, 1592s, 1570w, 1491w, 1463m, 1385vs, 1304s, 1154m, 1098w, 1070w, 1036w, 999m, 941w, 796s, 742m, 698s, 629w, 525w; Its results of elemental analyses is: theoretical value: H, 2.47; C, 35.32; N, 24.02%, experimental value: H, 2.34; C, 35.10; N, 24.17%.
This contains 4-amino-3 embodiment 2, two (the 2-pyridyl)-1,2 of 5-, and the preparation method of the silver of 4-triazole (I) title complex is:
Under the room temperature, with 0.1mmol AgNO
3Place the test tube bottom, use the 5mL dissolved in distilled water; Middle methyl alcohol and 1: 1 the mixing solutions 15mL of water volume ratio of adding; 0.05mmolL
-1Ligand L 5mL dissolve with methanol places the test tube upper strata; The lucifuge sealing and standing is 10 days then, and colourless bulk-shaped monocrystal appears in the place, boundary that connects of solution interface on the test tube wall.Crystal is used distilled water and washing with alcohol successively, and vacuum-drying is target product, and its productive rate is about 62%.The main infrared absorption peak of this target product is: 1631w, 1592s, 1570w, 1491w, 1463m, 1385vs, 1304s, 1154m, 1098w, 1070w, 1036w, 999m, 941w, 796s, 742m, 698s, 629w, 525w; Its results of elemental analyses is: theoretical value: H, 2.47; C, 35.32; N, 24.02%, experimental value: H, 2.34; C, 35.10; N, 24.17%.
This contains 4-amino-3 embodiment 3, two (the 2-pyridyl)-1,2 of 5-, and the preparation method of the silver of 4-triazole (I) title complex is:
Under the room temperature, with 0.08mmolAgNO
3Place the test tube bottom, use the 5mL dissolved in distilled water; Middle methyl alcohol and 1: 1 the mixing solutions 25mL of water volume ratio of adding; 0.05mmolL
-1Ligand L 5mL dissolve with methanol places the test tube upper strata; The lucifuge sealing and standing is 10 days then, and colourless bulk-shaped monocrystal appears in the place, boundary that connects of solution interface on the test tube wall.Crystal is used distilled water and washing with alcohol successively, and vacuum-drying is target product, and its productive rate is about 60%.The main infrared absorption peak of this target product is: 1631w, 1592s, 1570w, 1491w, 1463m, 1385vs, 1304s, 1154m, 1098w, 1070w, 1036w, 999m, 941w, 796s, 742m, 698s, 629w, 525w; Its results of elemental analyses is: theoretical value: H, 2.47; C, 35.32; N, 24.02%, experimental value: H, 2.34; C, 35.10; N, 24.17%.
This contains 4-amino-3 embodiment 4, two (the 2-pyridyl)-1,2 of 5-, and the preparation method of the silver of 4-triazole (I) title complex is:
With 0.05mmolAgNO
3Use the 5mL dissolved in distilled water, with 0.05mmolL
-1Ligand L 5mL dissolve with methanol, both direct mixing and stirring are filtered then, leave standstill solvent flashing, and colourless bulk-shaped monocrystal appears in beaker bottom after 5 days.Crystal is used distilled water and washing with alcohol successively, and vacuum-drying is target product, and its productive rate is about about 80%.The main infrared absorption peak of this target product is: 1631w, 1592s, 1570w, 1491w, 1463m, 1385vs, 1304s, 1154m, 1098w, 1070w, 1036w, 999m, 941w, 796s, 742m, 698s, 629w, 525w; Its results of elemental analyses is: theoretical value: H, 2.47; C, 35.32; N, 24.02%, experimental value: H, 2.35; C, 35.11; N, 24.16%.
This contains 4-amino-3 embodiment 5, two (the 2-pyridyl)-1,2 of 5-, and the preparation method of the silver of 4-triazole (I) title complex is:
With 0.1mmol AgNO
3Use the 6mL dissolved in distilled water, with 0.05mmolL
-1Ligand L 6mL dissolve with methanol, both direct mixing and stirring are filtered then, leave standstill solvent flashing, and colourless bulk-shaped monocrystal appears in beaker bottom after 6 days.Crystal is used distilled water and washing with alcohol successively, and vacuum-drying is target product, and its productive rate is about about 85%.The main infrared absorption peak of this target product is: 1631w, 1592s, 1570w, 1491w, 1463m, 1385vs, 1304s, 1154m, 1098w, 1070w, 1036w, 999m, 941w, 796s, 742m, 698s, 629w, 525w; Its results of elemental analyses is: theoretical value: H, 2.47; C, 35.32; N, 24.02%, experimental value: H, 2.35; C, 35.11; N, 24.16%.
This contains 4-amino-3 embodiment 6, two (the 2-pyridyl)-1,2 of 5-, and the preparation method of the silver of 4-triazole (I) title complex is:
With 0.08mmolAgNO
3Use the 8mL dissolved in distilled water, with 0.05mmolL
-1Ligand L 5mL dissolve with methanol, both direct mixing and stirring are filtered then, leave standstill solvent flashing, and colourless bulk-shaped monocrystal appears in beaker bottom after 7 days.Crystal is used distilled water and washing with alcohol successively, and vacuum-drying is target product, and its productive rate is about about 75%.The main infrared absorption peak of this target product is: 1631w, 1592s, 1570w, 1491w, 1463m, 1385vs, 1304s, 1154m, 1098w, 1070w, 1036w, 999m, 941w, 796s, 742m, 698s, 629w, 525w; Its results of elemental analyses is: theoretical value: H, 2.47; C, 35.32; N, 24.02%, experimental value: H, 2.35; C, 35.11; N, 24.16%.
This contains 4-amino-3 embodiment 7, two (the 2-pyridyl)-1,2 of 5-, and the preparation method of the silver of 4-triazole (I) title complex is:
With 0.05mmol AgNO
3And 0.05mmolL
-1Ligand L is dissolved in stirring at room in the 20mL distilled water, after mixing, places reactor, makes temperature of reaction kettle slowly rise to 60 ℃, keeps this temperature 3 days, reduces to room temperature then automatically, can obtain colourless bulk crystals.Crystal is used distilled water and washing with alcohol successively, and vacuum-drying is target product, and its productive rate is about about 55%.The main infrared absorption peak of this target product is: 1631w, 1592s, 1570w, 1491w, 1463m, 1385vs, 1304s, 1154m, 1098w, 1070w, 1036w, 999m, 941w, 796s, 742m, 698s, 629w, 525w; Its results of elemental analyses is: theoretical value: H, 2.47; C, 35.32; N, 24.02%, experimental value: H, 2.36; C, 35.13; N, 24.14%.
This contains 4-amino-3 embodiment 8, two (the 2-pyridyl)-1,2 of 5-, and the preparation method of the silver of 4-triazole (I) title complex is:
With 0.1mmol AgNO
3And 0.05mmolL
-1Ligand L is dissolved in stirring at room in the 18mL distilled water, after mixing, places reactor, makes temperature of reaction kettle slowly rise to 60 ℃, keeps this temperature 3 days, reduces to room temperature then automatically, can obtain colourless bulk crystals.Crystal is used distilled water and washing with alcohol successively, and vacuum-drying is target product, and its productive rate is about about 55%.The main infrared absorption peak of this target product is: 1631w, 1592s, 1570w, 1491w, 1463m, 1385vs, 1304s, 1154m, 1098w, 1070w, 1036w, 999m, 941w, 796s, 742m, 698s, 629w, 525w; Its results of elemental analyses is: theoretical value: H, 2.47; C, 35.32; N, 24.02%, experimental value: H, 2.36; C, 35.13; N, 24.14%.
This contains 4-amino-3 embodiment 9, two (the 2-pyridyl)-1,2 of 5-, and the preparation method of the silver of 4-triazole (I) title complex is:
With 0.08mmol AgNO
3And 0.05mmolL
-1Ligand L is dissolved in stirring at room in the 15mL distilled water, after mixing, places reactor, makes temperature of reaction kettle slowly rise to 60 ℃, keeps this temperature 3 days, reduces to room temperature then automatically, can obtain colourless bulk crystals.Crystal is used distilled water and washing with alcohol successively, and vacuum-drying is target product, and its productive rate is about about 55%.The main infrared absorption peak of this target product is: 1631w, 1592s, 1570w, 1491w, 1463m, 1385vs, 1304s, 1154m, 1098w, 1070w, 1036w, 999m, 941w, 796s, 742m, 698s, 629w, 525w; Its results of elemental analyses is: theoretical value: H, 2.47; C, 35.32; N, 24.02%, experimental value: H, 2.36; C, 35.13; N, 24.14%.
Followingly get gained 4-amino-3 among the embodiment 1～9 respectively, two (the 2-pyridyl)-1,2 of 5-, the silver of 4-triazole (I) title complex further characterizes, and its process is as follows:
(1) crystal structure determination of title complex
The monocrystalline of choosing suitable size at microscopically at room temperature carries out the X-ray diffraction experiment.On Bruker Apex II CCD diffractometer, use alpha-ray through the Mo-K of graphite monochromator monochromatization
With
Mode is collected diffraction data.Carry out reduction of data with Bruker SAINT program.Diffraction data carries out absorption correction with the SADABS program.Crystalline structure is solved in conjunction with difference Fourier is synthetic by direct method.All non-hydrogen atom coordinate and anisotropic parameters carry out the complete matrix least-squares refinement, and the hydrogen atom position is determined by theoretical mode computation.Detailed axonometry data see Table 1, and important bond distance and bond angle data see Table 2.Crystalline structure is seen Fig. 1 respectively, Fig. 2 and Fig. 3.
(2) the solid fluorescence performance study of title complex
Complex crystal sample after enrichment is handled, through further grinding, carry out the test of solid fluorescence: title complex excites at the 372nm place, obtains maximum emission peak at the 425nm place, sees Fig. 4 (instrument model: Varian, Cary Eclipse).
(3) the X-ray powder diffraction (XPRD) of title complex characterizes
The XPRD of title complex characterizes and shows that it has reliable phase purity, for its application as fluorescent material provides assurance, see Fig. 5 (instrument model: Rigaku, D/Max-2500).
(4) thermal stability of title complex characterizes
The thermogravimetric analysis of title complex characterizes and shows that its skeleton still can stable existence about near 250 ℃, has higher thermostability, for its further Application and Development as material provides the thermostability assurance, see Fig. 6 (instrument model: Siemens, NETZSCH TG209).
Can be seen that by above-mentioned characterization result complex crystal of the present invention belongs to rhombic system, spacer is P2
12
12
1, unit cell parameters is
α=90 °, β=90 °, γ=90 °,
Title complex is by the positively charged ion unit [Ag (L)] of one dimension spiral chain-like structure
+And NO
3 -Negatively charged ion is formed, wherein Ag
IBe the tetrahedral coordination environment of distortion, the positively charged ion unit is parallel accumulation along the b direction of principal axis simultaneously, forms the passage that extends.
Above embodiment only is used to illustrate content of the present invention, and in addition, the present invention also has other embodiment.But all employings are equal to replaces or technical scheme that the equivalent deformation mode forms all drops in protection scope of the present invention.
The main crystallographic data of table 1 title complex
aR
1＝∑(||F
o|-|F
c||)/∑|F
o|；
bwR
2＝[∑w(|F
o|
2-|F
c|
2)
2/∑w(F
o 2)
2]
1/2
The main bond distance of table 2 title complex
And bond angle [°] *
* symmetrical code: #1x-1/2 ,-y+3/2 ,-z.
Claims (4)
1. one kind contains 4-amino-3, two (the 2-pyridyl)-1,2 of 5-, and the silver of 4-triazole (I) title complex, it is characterized in that: described title complex has following chemical formula, that is: { [AgL] (NO
3)
∞, wherein L is a 4-amino-3, two (the 2-pyridyl)-1,2 of 5-, and the 4-triazole, the L skeleton symbol is as follows:
And described complex crystal belongs to rhombic system, and spacer is P2
12
12
1, unit cell parameters is
α=90 °, β=90 °, γ=90 °,
2. the 4-amino-3 that contains as claimed in claim 1, two (the 2-pyridyl)-1,2 of 5-, the preparation method of the silver of 4-triazole (I) title complex is characterized in that this method comprises the steps: under the room temperature AgNO
3Water-soluble formation bottom solution; Secondly adding above bottom solution mainly by volume ratio is that 1: 1 first alcohol and water mixes the buffer layer that forms, and interpolation contains 0.01molL above buffer layer thereafter
-1The methanol solution of ligand L forms layering diffusion reaction system, ligand L and AgNO in the reaction system
3Mol ratio be 1: 1～1: 2, the volume ratio of upper, middle and lower-ranking solution is 1: 3: 1～1: 5: 1; With this layering diffusion reaction system lucifuge sealing and standing 10 days, colourless bulk-shaped monocrystal appears the place, boundary that connects of solution interface at the middle and upper levels to layering diffusion reaction system, this monocrystalline is separated, through washing, drying treatment, obtain target product successively.
3. the 4-amino-3 that contains as claimed in claim 1, two (the 2-pyridyl)-1,2 of 5-, the preparation method of the silver of 4-triazole (I) title complex is characterized in that this method is: under the room temperature with AgNO
3Water-soluble formation silver salt solution is dissolved in ligand L methyl alcohol simultaneously and forms ligand solution, ligand L and AgNO in the reaction system
3Mol ratio be 1: 1～1: 2, then silver salt solution and ligand solution are directly mixed filter reaction mixture, filtrate is left standstill volatilization, to filtrate, colourless bulk-shaped monocrystal occurs, this monocrystalline is separated, through washing, drying treatment, obtain target product successively.
4. the 4-amino-3 that contains as claimed in claim 1, two (the 2-pyridyl)-1,2 of 5-, the preparation method of the silver of 4-triazole (I) title complex is characterized in that this method is: at room temperature with 0.1mmol AgNO
3Soluble in water and mix ligand L and AgNO in the reaction system with the 0.05mmol ligand L
3Mol ratio be 1: 2, again with reaction mixture with per hour 10 ℃ be heated to 60 ℃, kept this temperature 3 days, reduce to room temperature then, can obtain colourless bulk crystals, this monocrystalline is separated, successively through the washing, drying treatment, obtain target product.
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