CN101798319B - 2, 3, 4, 5-tetrahydrofuran tetracarboxylic acid and 3-(2-pyridyl) pyrazol-mixed cadmium composition, as well as preparation method and application thereof - Google Patents
2, 3, 4, 5-tetrahydrofuran tetracarboxylic acid and 3-(2-pyridyl) pyrazol-mixed cadmium composition, as well as preparation method and application thereof Download PDFInfo
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Abstract
一种2，3，4，5-四氢呋喃四羧酸和3-(2-吡啶基)吡唑混配镉配合物及其制备方法与应用，属于过渡金属配合物材料技术领域。配合物是下述化学式的配合物：{[Cd 2(L)(pp) 2(H 2O)](H 2O) 2.5} ∞，其中L＝2，3，4，5-四氢呋喃四羧基阴离子配体，pp＝3-(2-吡啶基)吡唑，配合物采用试管分层扩散法制备。本发明展现的合成方法，条件温和、产率高、可重现性好。配合物的荧光光谱数据显示该类材料能够发射稳定的蓝色荧光，有望作为荧光材料在材料科学领域得到应用。A cadmium complex mixed with 2,3,4,5-tetrahydrofuran tetracarboxylic acid and 3-(2-pyridyl)pyrazole and its preparation method and application belong to the technical field of transition metal complex materials. The complex is a complex of the following chemical formula: {[Cd 2 (L)(pp) 2 (H 2 O)](H 2 O) 2.5 } ∞ , where L=2,3,4,5-tetrahydrofuran tetracarboxy Anionic ligand, pp=3-(2-pyridyl)pyrazole, the complex was prepared by test tube layered diffusion method. The synthesis method presented by the invention has mild conditions, high yield and good reproducibility. The fluorescence spectrum data of the complex shows that this kind of material can emit stable blue fluorescence, and it is expected to be used as a fluorescent material in the field of material science.
Description
Technical field
The invention belongs to transition metal complex material technology field, be specifically related to a kind of 2,3,4,5-tetrahydrofuran (THF) tetracarboxylic acid and 3-(2-pyridyl) pyrazol-mixed cadmium title complex and preparation method thereof and application.
Background technology
D in recent years
10Metal complexes is owing to have novel structure and potential high-performance (as: fluorescence, fractionation by adsorption, electricity lead and catalysis etc.) has received people's very big concern and by a large amount of synthetic and research, also become one of forward position research focus of coordination chemistry simultaneously.The carboxylic-acid part receives people's very big concern always in ligand polymer is constructed, such ligand moiety or all take off proton makes part show various coordination mode flexibly, obtains the compound of different structure.Have the carboxylic acid part that enriches coordination mode, particularly fragrance contains phenyl ring, contains naphthalene nucleus, contains anthracene nucleus, contains the pyrene ring, contains the carboxyl class part of rigid backbone such as perylene ring and derivative series thereof by the extensive and a large amount of research of people.
Aromatic ring frame generally has the conjugated pi system, easily by forming π ... pi accumulation and C-H ... supramolecules such as π interact and play important effect in the forming processes of respective metal title complex.In general, rigid ligand is in the coordination process, and considerable change does not take place for the spacing and the angle of part coordination between cog, makes them have less uncertain factor in complex formation.Therefore the easiest realization of ligand polymer of constructing of such part is to the prediction of network structure.With respect to these rigid ligand and ligand polymer thereof, the research of constructing ligand polymer with flexible part then has more can not expection property.Flexible part refers to those and have at least two adjacent non-colinear σ keys (for example C-C-C, C-O-C or C-N-C) on the skeleton that connects coordinating group, and the behavior when constructing network structure of this part and rigid ligand is different.As previously mentioned, use rigid ligand to help joining the prediction and the regulation and control of polymers structure; And for flexible part, because the σ key can rotate freely, this class part can take multiple configuration to come self-identifying and assembling according to the variation of coordination environment, thereby reaches optimum matching.Such linking group has the certain deformation coordination ability when coordination, thereby the shape of coordination interdental space, angle and linking group can both be adjusted to adapt to coordination environment, the title complex of easier formation structure uniqueness.Because these characteristics of flexible part, the title complex that makes their guiding construct may have not available special property of rigid ligand title complex and functions such as structure diversity, hole adjustable size joint, therefore in the last few years, the research of using flexible part to construct " flexibility " ligand polymer network had also caused researchist's attention.For example, people such as Sevov adopt 2,3,4, and 5-tetrahydrofuran (THF) tetracarboxylic acid is that part has prepared a series of Zn
II, Co
II, Cu
II, and Mn
IITitle complex (Wang, X.-Y.; Sevov, S.C.Chem.Mater.2007,19,3763-3766; Wang, X.-Y.; Scancella M.; Sevov, S.C.Chem.Mater.2007,19,4506-4513); People such as Tong utilize 1,2,3,4,5, and 6-hexamethylene hexacarboxylic acid has prepared two Cd metallic organic framework title complex (Wang, J. with nanoscale hole of three-dimensional structure; Zhang, Y.-H.; Tong, M.-L.Chem.Commun.2006,3166-3168).
3-(2-pyridyl) pyrazoles is one and is similar to 2,2 '-chelating ligand of dipyridyl, but its difference is to have asymmetry, it can be with bidentate chelating pattern and metallic ion coordination (card angle chelating ligand), and the H that can take off again on the pyrazoles N joins-chelating pattern and metallic ion coordination with three bridge works.When forming title complex, 3-(2-pyridyl) pyrazoles forms an electronegative part by the H that takes off on the pyrazoles N, thereby plays the effect of balancing charge, can be used as the good chelating ligand of metal ion, thereby regulates and control the space dimensionality of its coordinated network.
Carboxylic-acid part mixed ligand coordination compound adopts hydro-thermal or solvent thermal synthesis method usually in the prior art, and all there is the temperature height in above synthetic method, danger is big, productive rate is low, sample is difficult to technological deficiencies such as purifies and separates.
Summary of the invention
The object of the present invention is to provide a kind of 2,3,4,5-tetrahydrofuran (THF) tetracarboxylic acid and 3-(2-pyridyl) pyrazol-mixed cadmium title complex and preparation method thereof and application.
For achieving the above object, the technical solution used in the present invention is as follows:
Of the present invention 2,3,4,5-tetrahydrofuran (THF) tetracarboxylic acid and 3-(2-pyridyl) pyrazol-mixed cadmium title complex is the title complex of following chemical formula: { [Cd
2(L) (pp)
2(H
2O)] (H
2O)
2.5}
∞, L=2 wherein, 3,4,5-tetrahydrofuran (THF) tetracarboxylic anion ligand, pp=3-(2-pyridyl) pyrazoles, wherein the molecular formula of L and pp is as follows respectively:
Described complex crystal belongs to oblique system, and spacer is P2 (1)/c, and unit cell parameters is a=12.1706 (13), b=15.5995 (17), c=15.8128 (17)
α=90, β=93.9810 (10), γ=90 °, V=2994.9 (6)
Basic structure is the one-dimensional chain of a double-core node, and center C d is the hexa-coordinate configuration of distortion.
The synthetic employing diffusion process of title complex: under the room temperature, cadmium metal salt is placed the test tube bottom, add dissolved in distilled water and form reaction solution A; Answering liquid A upper strata to add the mixed solution C of methyl alcohol and water; Adding is dissolved with 2, the part H of 6-lutidine on the mixed solution C upper strata
4The methyl alcohol reaction solution B of L and pp; Leave standstill diffusion then and obtained colourless bulk-shaped monocrystal in 20～30 days, successively with distilled water, ethanol and ether washing, be drying to obtain again.
Described cadmium metal salt is any one in vitriol, nitrate, perchlorate or their hydrate.
It is described that to answer the concentration of cadmium metal among the liquid A be 0.02～0.04molL
-1
The volume ratio of first alcohol and water is 1: 1～1: 1.2 in the described mixed solution C.
Part H among the described reaction solution B
4The mol ratio of L and pp is 1: 1; Part H among the reaction solution B
4The volumetric molar concentration of L is 1: 2 with the ratio of the volumetric molar concentration of answering cadmium metal salt among the liquid A.
Among the described reaction solution B 2,6-lutidine and part H
4The mol ratio of L is 4: 1～6: 1.
The volume ratio of answering liquid A, mixed solution C, reaction solution B is 1: 3: 1～1: 4: 1.
Of the present invention 2,3,4, the fluorescent chemicals of 5-tetrahydrofuran (THF) tetracarboxylic acid and 3-(2-pyridyl) pyrazol-mixed cadmium title complex aspect material as the application of fluorescent material.
The present invention is a chelate group with 3-(2-pyridyl) pyrazoles, 2,3,4, to be multiple tooth link group by the test tube layered approach of mild condition synthetic and characterized 2,3,4 for 5-tetrahydrofuran (THF) tetracarboxylic acid, 5-tetrahydrofuran (THF) tetracarboxylic acid and 3-(2-pyridyl) pyrazol-mixed cadmium title complex, and study its fluorescence property.
The synthetic method of title complex provided by the invention adopts Liquid Phase Diffusion method synthetic compound.Reaction solution A and reaction solution B are placed the bottom and the top of test tube respectively, and the middle buffer layer that adds at room temperature leaves standstill test tube then, and reaction solution A and B just have the interface to begin that mutual diffusion mutually is concurrent gives birth to reaction and generate title complex in the process of leaving standstill like this.This synthetic method at normal temperatures and pressures, mild condition, productive rate height, reproducibility are good, and can understand reaction process.
The fluorescence data of crystal prototype shows that this type of title complex has the stable fluorescence performance, can be used as fluorescent material and is applied at material science.The thermogravimetric analysis of title complex characterizes and shows that its skeleton still can stable existence about 300 ℃, has higher thermostability, for its further Application and Development as material provides the thermostability assurance.
Description of drawings
Fig. 1 is the Cd coordination environment figure of title complex;
Fig. 2 is the one-dimensional chain structure iron of title complex;
Fig. 3 is the solid fluorescence figure of title complex;
Fig. 4 is the powdery diffractometry synoptic diagram of title complex;
Fig. 5 is title complex thermogravimetric curve figure.
Embodiment
Below by embodiment the present invention is elaborated, but and do not limit the present invention in any way.
With 0.1mmol Cd (NO
3)
26H
2O places the test tube bottom, forms reaction solution A with the 5mL dissolved in distilled water; Middle methyl alcohol and 1: 1 the mixed solution 15mL of water volume ratio of adding; 0.05mmol H
4L and 0.05mmolpp 5mL dissolve with methanol adds 2, and 6-lutidine 0.035mL gets reaction solution B, places the test tube upper strata.Sealing and standing 25 days, colourless bulk-shaped monocrystal appears in the place, boundary that connects of solution interface on the test tube wall.Crystal washs with distilled water, ethanol and ether successively, vacuum-drying, and productive rate is about 50%.
Main infrared absorption peak is: 3417s (br), 1864w, 1590vs, 1430s, 1393vs, 1318m, 1297m, 1257m, 1220m, 1158m, 1137w, 1085m, 1015w, 990w, 968m, 940m, 897w, 852m, 829m, 775s, 691m, 639m, 613m.
With 0.2mmol Cd (ClO
4)
26H
2O places the test tube bottom, becomes reaction solution A with the 5mL dissolved in distilled water; The middle mixed solution 17.5mL that adds 1: 1.2 volume ratio of first alcohol and water; 0.10mmol H
4L and 0.10mmolpp 5mL dissolve with methanol adds 2, and 6-lutidine 0.05mL gets reaction solution B, places the test tube upper strata.Sealing and standing 28 days, colourless bulk-shaped monocrystal appears in the place, boundary that connects of solution interface on the test tube wall.Crystal washs with distilled water, ethanol and ether successively, vacuum-drying, and productive rate is 55%.
Main infrared absorption peak is: 3417s (br), 1864w, 1590vs, 1430s, 1393vs, 1318m, 1297m, 1257m, 1220m, 1158m, 1137w, 1085m, 1015w, 990w, 968m, 940m, 897w, 852m, 829m, 775s, 691m, 639m, 613m.
With 0.1mmol CdSO
4Place the test tube bottom, form reaction solution A with the 4mL dissolved in distilled water; The middle mixed solution 16mL that adds 1: 1 volume ratio of first alcohol and water; 0.05mmol H
4L and 0.05mmol pp 4mL dissolve with methanol, it is excessive 2 to add, 6-lutidine 0.035mL, reaction solution B, place the test tube upper strata.Sealing and standing 29 days, colourless bulk-shaped monocrystal appears in the place, boundary that connects of solution interface on the test tube wall.Crystal washs with distilled water, ethanol and ether successively, vacuum-drying, and productive rate is 52%.
Main infrared absorption peak is: 3417s (br), 1864w, 1590vs, 1430s, 1393vs, 1318m, 1297m, 1257m, 1220m, 1158m, 1137w, 1085m, 1015w, 990w, 968m, 940m, 897w, 852m, 829m, 775s, 691m, 639m, 613m.
With 0.15mmol Cd (NO
3)
26H
2O places the test tube bottom, forms reaction solution A with the 5mL dissolved in distilled water; The middle mixed solution 15mL that adds 1: 1 volume ratio of first alcohol and water; 0.075mmol H
4L and 0.075mmol pp 5mL dissolve with methanol add 2, and 6-lutidine 0.044mL gets reaction solution B, places the test tube upper strata.Sealing and standing 30 days, colourless bulk-shaped monocrystal appears in the place, boundary that connects of solution interface on the test tube wall.Crystal washs with distilled water, ethanol and ether successively, vacuum-drying, and productive rate is 55%.
Main infrared absorption peak is: 3417s (br), 1864w, 1590vs, 1430s, 1393vs, 1318m, 1297m, 1257m, 1220m, 1158m, 1137w, 1085m, 1015w, 990w, 968m, 940m, 897w, 852m, 829m, 775s, 691m, 639m, 613m.
The relevant characterization of title complex
(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 BrukerSmart 1000CCD diffractometer, use Mo-K through the graphite monochromator monochromatization
αRay (λ=0.71073
), with
Mode is collected diffraction data.Carry out reduction of data with Bruker SAINT program.The diffraction data of part-structure 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.The hydrogen atom of partial solvent water is handled with the method for difference Fourier peak-seeking.Detailed axonometry data see Table 1.Important bond distance and bond angle data see Table 2; Crystalline structure is seen Fig. 1 and Fig. 2.
(2) the solid fluorescence performance study of title complex
Complex crystal sample after enrichment is handled is through further milled processed, and carry out the test of solid fluorescence: title complex excites at the 363nm place, obtains maximum emission peak at the 428nm place, sees Fig. 3.(instrument model: HITACHI/F-7000).
(3) the XPRD phase purity 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, sees Fig. 4.(instrument model: Bruker/D8Advance).
(4) thermal stability of title complex characterizes
The thermogravimetric analysis of title complex characterizes and shows that its skeleton still can stable existence about 300 ℃, has higher thermostability, for its further Application and Development as material provides the thermostability assurance, sees Fig. 5.(instrument model: Perkin-Elmin Diamond TG/DTA).
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 [°]
*
*Symmetry code: #1-x-1/2, y+1/2 ,-z+1/2 #2-x-1/2, y-1/2 ,-z+1/2
Claims (9)
1. one kind 2,3,4,5-tetrahydrofuran (THF) tetracarboxylic acid and 3-(2-pyridine) pyrazol-mixed cadmium title complex, it is characterized in that: this title complex has following chemical formula: { [Cd
2(L) (pp)
2(H
2O)] (H
2O)
2.5}
∞, L=2 wherein, 3,4,5-tetrahydrofuran (THF) tetracarboxylic anion ligand, pp=3-(2-pyridyl) pyrazoles;
Described complex crystal belongs to oblique system, and spacer is P2 (1)/c, and unit cell parameters is a=12.1706 (13)
B=15.5995 (17)
C=15.8128 (17)
α=90 °, β=93.9810 (10) °, γ=90 °, V=2994.9 (6)
Basic structure is the one-dimensional chain of a double-core node, and center C d is the hexa-coordinate configuration of distortion.
2. claim 1 described 2,3,4, the preparation method of 5-tetrahydrofuran (THF) tetracarboxylic acid and 3-(2-pyridine) pyrazol-mixed cadmium title complex, it is characterized in that: it comprises the steps: this method under the room temperature, and cadmium metal salt is placed the test tube bottom, adds dissolved in distilled water and forms reaction solution A; The mixed solution C that adds methyl alcohol and water on reaction solution A upper strata; Adding is dissolved with 2, the part H of 6-lutidine on the mixed solution C upper strata
4The methyl alcohol reaction solution B of L and pp; Leave standstill diffusion then and obtained colourless bulk-shaped monocrystal in 20～30 days, successively with distilled water, ethanol and ether washing, be drying to obtain again.
3. according to claim 22,3,4, the preparation method of 5-tetrahydrofuran (THF) tetracarboxylic acid and 3-(2-pyridine) pyrazol-mixed cadmium title complex is characterized in that: described cadmium metal salt is any one in vitriol, nitrate, perchlorate or their hydrate.
4. according to claim 2 or 3 described 2,3,4, the preparation method of 5-tetrahydrofuran (THF) tetracarboxylic acid and 3-(2-pyridine) pyrazol-mixed cadmium title complex, it is characterized in that: the concentration of cadmium metal is 0.02～0.04molL among the reaction solution A
-1
5. according to claim 22,3,4, the preparation method of 5-tetrahydrofuran (THF) tetracarboxylic acid and 3-(2-pyridine) pyrazol-mixed cadmium title complex, it is characterized in that: the volume ratio of first alcohol and water is 1: 1～1: 1.2 in the mixed solution C.
6. according to claim 22,3,4, the preparation method of 5-tetrahydrofuran (THF) tetracarboxylic acid and 3-(2-pyridine) pyrazol-mixed cadmium title complex is characterized in that: part H among the reaction solution B
4The mol ratio of L and pp is 1: 1; Part H among the reaction solution B
4The ratio of the volumetric molar concentration of cadmium metal salt is 1: 2 among the volumetric molar concentration of L and the reaction solution A.
7. according to claim 62,3,4, the preparation method of 5-tetrahydrofuran (THF) tetracarboxylic acid and 3-(2-pyridine) pyrazol-mixed cadmium title complex is characterized in that: among the reaction solution B 2, and 6-lutidine and part H
4The mol ratio of L is 4: 1～6: 1.
8. according to claim 22,3,4, the preparation method of 5-tetrahydrofuran (THF) tetracarboxylic acid and 3-(2-pyridine) pyrazol-mixed cadmium title complex, it is characterized in that: the volume ratio of reaction solution A, mixed solution C, reaction solution B is 1: 3: 1～1: 4: 1.
9. claim 1 is described 2,3,4, and 5-tetrahydrofuran (THF) tetracarboxylic acid and 3-(2-pyridine) pyrazol-mixed cadmium title complex is as the application of fluorescent material.
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| CN103509040A (en) * | 2012-06-26 | 2014-01-15 | 宁波大学 | Coordination polymer with high thermal stability and fluorescence properties and preparation method thereof |
| CN103804398B (en) * | 2014-01-10 | 2017-12-08 | 宁波大学 | A kind of 2 (base of 1H pyrazoles 3) pyridine copper complexes and its preparation method and application |
| CN104130276A (en) * | 2014-06-13 | 2014-11-05 | 南京林业大学 | Fumaropimaric acid water cluster coordination polymer, and preparation method and application thereof |
| CN104311584A (en) * | 2014-10-09 | 2015-01-28 | 济南大学 | Synthesis and application of cadmium metal organic complex second-order nonlinear optical material |
| CN105237337B (en) * | 2015-11-11 | 2017-07-25 | 遵义医学院 | The synthetic method of novel 5-[10-(9-carboxyanthracenyl)]-isophthalic acid |
| CN105566362A (en) * | 2016-01-18 | 2016-05-11 | 长春工业大学 | Furan dicarboxylic acid and metal cadmium organic framework material and preparation method |
| CN108299475A (en) * | 2018-02-06 | 2018-07-20 | 云南农业大学 | 3-dimensional metal based on 5- chlorothiophene -2- carboxylic acids and 4,4 '-bipyridyls-organic backbone crystalline material and preparation method |
| CN109830174A (en) * | 2019-03-21 | 2019-05-31 | 赖正俊 | Paper base group of the lanthanides intelligent anti-counterfeiting device |
| CN111518282B (en) * | 2020-06-24 | 2022-03-04 | 江苏理工学院 | Visible-light-catalyzed degradation of organic dyes with cadmium hydroxypyrazolecarboxylate coordination polymers and their preparation and application |
| CN114106342B (en) * | 2020-08-27 | 2022-11-01 | 江西省科学院应用化学研究所 | A kind of coordination polymer based on Cd(II) and its preparation method and application |
| CN116083075A (en) * | 2021-11-08 | 2023-05-09 | 新疆农业大学 | Manganese-based pyridine fluorescent crystal material, preparation method and application |
| CN114685807B (en) * | 2022-04-21 | 2023-03-14 | 东南大学 | Cadmium coordination polymer based on pyrazole carboxylic acid ligand and preparation method thereof |
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