CN105646897B - Coordination polymer with selective ion exchange performance and its application - Google Patents
Coordination polymer with selective ion exchange performance and its application Download PDFInfo
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- CN105646897B CN105646897B CN201610024415.1A CN201610024415A CN105646897B CN 105646897 B CN105646897 B CN 105646897B CN 201610024415 A CN201610024415 A CN 201610024415A CN 105646897 B CN105646897 B CN 105646897B
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/008—Supramolecular polymers
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J45/00—Ion-exchange in which a complex or a chelate is formed; Use of material as complex or chelate forming ion-exchangers; Treatment of material for improving the complex or chelate forming ion-exchange properties
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- C—CHEMISTRY; METALLURGY
- C30—CRYSTAL GROWTH
- C30B—SINGLE-CRYSTAL GROWTH; UNIDIRECTIONAL SOLIDIFICATION OF EUTECTIC MATERIAL OR UNIDIRECTIONAL DEMIXING OF EUTECTOID MATERIAL; REFINING BY ZONE-MELTING OF MATERIAL; PRODUCTION OF A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; SINGLE CRYSTALS OR HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; AFTER-TREATMENT OF SINGLE CRYSTALS OR A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; APPARATUS THEREFOR
- C30B29/00—Single crystals or homogeneous polycrystalline material with defined structure characterised by the material or by their shape
- C30B29/54—Organic compounds
- C30B29/58—Macromolecular compounds
Abstract
The present invention relates to a kind of preparation of coordination polymer and its applications.The chemical formula of complex is：[Ag(L)(NO3)](CH3OH)(H2O)2, wherein L=4,5 bis- (4 pyridyl groups) 3 (2 pyridyl group), 1,2,4 triazole.It is under conditions of normal temperature and pressure is protected from light, by AgNO3It is configured to aqueous solution and is added drop-wise to test tube bottom, after buffer layer is added, the ligand L for being dissolved in methanol is slowly added dropwise to test tube upper layer, be then allowed to stand volatilization, colourless bulk crystals have been grown in the middle part of about 3~4 days test tubes.It is demonstrated experimentally that not only selectively with high rhenium acid group ion anion exchange can occur for the nitrate ion in the material cavity, stronger ability also is shown to the rich absorbent of rhenium metal.The material overcomes the limitation of existing anion-exchange material, there is that exchange process is simple and practicable, exchange velocity is fast, thus is expected to obtain practical application in ion exchange material field.
Description
Technical field
The invention belongs to the synthesis of novel inorganic-organic Hybrid Materials, structure and performance technologies fields, are related specifically to
A kind of bis- (4- pyridyl groups) -3- (2- the pyridyl groups) -1,2,4- triazoles-silver coordination polymerizations of 4,5- with Three-dimensional Open skeleton structure
The preparation of object and its application in terms of chosen anion switching performance.
Background technology
Coordination polymer is the self assembly by inorganic metal ion and organic ligand and is formed, and has been had both organic and inorganic
The property of compound, and coordination polymer is readily synthesized again, large specific surface area, topological structure are abundant, structure is controllable etc.
Advantage, thus its have in optical material, electricity material, superconductor, catalysis material and ion exchange material etc. it is huge
Big application potential.As more and more scientific workers put into the research of complex functional structure, nowadays
A large amount of topological structure difference is synthesized, and there is the polycomplexation of excellent performance in light, electricity, magnetic, catalysis, absorption etc.
Close object.Breakthrough in terms of these functions and progress not only have great importance to Coordinative Chemistry subject itself, while also pushing away
The development of the related disciplines such as biochemistry, materials chemistry is moved.Usual coordination polymer have can microcosmic regulation and control cavity, and
And also have thermal stability high and the excellent performance insoluble in common organic solvents.The opening pore passage structure of coordination polymer can
To accommodate some guest components, these guest components may be anion or solvent molecule, if wherein anion is not involved in and matches
Position, will just play the role of occupying with supporting network structural cavities and balancing charge, in addition to this, anion can also pass through
Inducing ligand isomery is to form different network structures.The above feature so that coordination polymer is as a kind of novel
Ion exchange material, which is gathered around, to have broad application prospects, for example, the quantitative analysis of pollutant and selective absorbing in environment, metal from
Determination of trace and isotope geochemistry research of son etc..
Rhenium metal is a kind of very rare dispersed elements, be now widely used for the modern industrial sector such as petroleum industry and
Auto industry, electronics industry and aerospace industry etc..Although China's rhenium yield relative abundance, due to further opening up to rhenium purposes
Exhibition, leads to the in short supply of rhenium, and rarely has the report for the material for possessing rhenium superelevation accumulation ability at this stage.Cationic metal-
Organic frame can be made of nitrogen heterocyclic ring class multidentate ligand and metal ion, for balancing charge and not with metallic ion coordination
Anion in occupation of the gap of frame, therefore higher accumulation ability can be shown to high rhenium acid group.
Invention content
It is an object of the present invention to provide the coordination polymers and preparation method thereof with Three-dimensional Open skeleton.
It is another object of the present invention to provide precursor needed for the coordination polymer for preparing Three-dimensional Open skeleton
Close object and preparation method thereof.
It is yet a further object of the present invention to provide the crystal with Three-dimensional Open skeleton coordination polymer.
It is yet a further object of the present invention to provide the coordination polymers of Three-dimensional Open skeleton or monocrystal in selectivity
Application in terms of ion exchange.
To achieve the above object, the technology contents that the present invention is disclosed directly below：
Coordination polymer with Three-dimensional Open skeleton：Chemical formula is [Ag (L) (NO3)](CH3OH)(H2O)2, wherein L's
Structural formula is as follows：
L
The preparation method of coordination polymer of the present invention, it is characterised in that：It, will under conditions of normal temperature and pressure is protected from light
The AgNO of 0.1~0.5 mmol3It is configured to aqueous solution and is added drop-wise to test tube bottom, after buffer layer is added, the ligand L of methanol will be dissolved in
Test tube upper layer is slowly added dropwise in 0.1~0.5 mmol, is then allowed to stand volatilization, it is brilliant that colourless bulk has been grown within about 3~4 days in the middle part of test tube
Body.
The triazole organic ligand of three pyridyl groups substitution of the present invention has following structural formula：
L
The existence forms of L at room temperature are white solid.The application of this organic matter is to prepare stable coordination polymer, this
Kind compound can take a variety of different coordinations as the multidentate ligand containing multi-functional group when from metallic ion coordination
Mode.Preparation method is carried out by following specific steps：
By N- (4- pyridyl groups) -2- pyridines-thioamides and Isoniazid n-Butanol soluble, it is heated to reflux 30~
Stop heating after 40 hours, be cooled to room temperature, decompression filters, and is washed with ethyl alcohol and obtains light yellow solid afterwards three times；Wherein N- (4-
Pyridyl group) -2- pyridines-thioamides：The molar ratio of 2- pyridinecarboxylic hydrazines is 1:1~1: 2.With ethyl alcohol recrystallization, obtain white
Color solid product.
The present invention is as follows：
Building-up process：By N- (4- pyridyl groups) -2- pyridines-thioamides（21.5 g, 0.1 mol）With 4- pyridinecarboxylics
Hydrazine（13.7 g, 0.1 mol）With 200 mL n-Butanol solubles, stops heating after being heated to reflux 36 hours, be cooled to room temperature, subtract
Pressure filters, and is washed with ethyl alcohol and obtains light yellow solid afterwards three times.With ethyl alcohol recrystallization, white powder solid product is obtained.With point
Balance precise is analysed, it is 65% to calculate yield.
The present invention further discloses the coordination polymer crystals with Three-dimensional Open skeleton structure, it is characterised in that described
Coordination polymer crystal belongs to monoclinic system, and coordination polymer Advances in crystal X-ray diffraction structure determination is in Bruker Apex II
It is carried out on CCD diffractometers.At 296 (2) K, swept with ω with through graphite monochromatised Mo K alpha rays (λ=0.71073)
The mode of retouching collects point diffraction, and the data of collection carry out semiempirical absorption correction by SAINT programe reductions and with SADABS methods.
The SHELXS and SHELXL that SHELXTL programs are respectively adopted in structure elucidation and refine are completed, and pass through complete matrix least square method
It is rightF 2It is modified to obtain the coordinate and anisotropic parameters of whole non-hydrogen atoms.Infrared spectrum is by AVATAR-370
(Nicolet) spectrometer measures, KBr tablettings, collects 400-4000 cm–1Interval censored data；Elemental analysis is by CE-440
(Leemanlabs) elemental analyser measures；X-ray powder diffractions (PXRD) style is by Bruker D8 Advance diffractometers
It measures, Cu targets (λ=1.5406), 0.2 °/min of sweep speed, crystal parameters are as follows：
The present invention further discloses the coordination polymer of three-dimensional open structure answering in terms of selective ion exchange
With.Wherein the selective ion exchange refers to：The exchange of high rhenium acid group ion.
Coordination polymer disclosed by the invention with Three-dimensional Open skeleton is compared with the same type material being currently known, tool
There are many unique advantage is as follows：
（1）This ion exchange material only has a selective function of exchange for high rhenium acid group ion, and for it is other it is cloudy from
It is sub then do not have this feature.
（2）Preparing for the material is simple and practicable, and the reaction time is short, easy post-processing and yield is higher.And it is commonly known
Such material prepare yield it is relatively low and post-processing it is cumbersome.
（3）This material be for the exchange reaction of high rhenium acid group it is irreversible, can be to avoid side reaction in exchange process
Occur, there is higher exchange efficiency.
The present invention is prepared for a kind of there is special selective coordination polymer type ion to hand over high rhenium acid group anion
Conversion materials have the advantages that synthesis is simple, easy to operate, stability is good, yield height and high ion-exchanging efficiency.The present invention with
Position chemistry, Supramolecular Assembling, solid state chemistry, mineral crystal engineering and materials chemistry etc. are with wide significance and important
Application value.
Description of the drawings:
Ag in Fig. 1 complexsIThe coordination context diagram of ion；
The three-dimensional lumen schematic diagram of Fig. 2 complexs；
The experiment of Fig. 3 complex powder diffraction (PXRD) styles and theoretical compares figure；
Powder diffraction (PXRD) style compares figure before and after ion exchange occurs for Fig. 4 complexs；
Infrared (FT-IR) spectral comparison figure before and after ion exchange occurs for Fig. 5 complexs.
Specific implementation mode
The present invention is described below by specific embodiment.Unless stated otherwise, technological means used in the present invention
It is method known in those skilled in the art.In addition, embodiment is interpreted as illustrative, it is not intended to limit the present invention
Range, the spirit and scope of the invention are limited only by the claims that follow.To those skilled in the art, without departing substantially from this
Under the premise of invention spirit and scope, various changes or change to material component and dosage progress in these embodiments
It belongs to the scope of protection of the present invention.
N- (4- pyridyl groups) -2- pyridines-thioamides and Isoniazid can be bought by Reagent Company to be obtained.
The present invention complex it is characterized in that：The complex crystal belongs to monoclinic system, and space group isP21 n, structure cell
Parameter isa = 10.015(2) Å, b = 14.505(3) Å, c = 15.454(3) Å, α = γ = 90 o, β =
104.390(3) Å, V = 2174.5(8) Å3.Basic structure is a three-dimensional coordinated network structure, and there are a kind of AgICoordination
Environment, AgIFor the four-coordination configuration of distortion.
In the preparation method of complex of the present invention, under conditions of normal temperature and pressure is protected from light, by the AgNO of 0.1 mmol3It is molten
It is placed in test tube bottom in water, buffer layer is added, then dissolves 0.1 mmol ligand Ls with methanol, and be slowly added drop-wise to AgNO3
The upper layer of aqueous solution stands volatilization and obtains colourless bulk-shaped monocrystal product in 3~5 days.Wherein N- (4- pyridyl groups) -2- pyridines-thio
Amide, Isoniazid are commercially available.
Embodiment 1：
The preparation of more Pyridine Bridges connection organic ligand (L) containing 1,2,4- triazoles and discussion of results
1. compound experiment and post-processing：
By N- (4- pyridyl groups) -2- pyridines-thioamides（21.5 g, 0.1 mol）And Isoniazid（13.7 g,
0.1 mol）With 200 mL n-Butanol solubles, stop heating after being heated to reflux 36 hours, be cooled to room temperature, decompression filters, and uses second
Alcohol washing obtains light yellow solid afterwards three times.With ethyl alcohol recrystallization, white powder product is obtained.With assay balance precise,
It is 46% to calculate yield.
2. result and discussion：
Analytical and testing instrument：
Elemental analysis, C, H, N content, which measure, uses CE-440 (Leemanlabs) type elemental analyser
Infrared spectrum, AVATAR-370 (Nicolet) Fourier infrared spectrograph
Elemental analysis：Theoretical value (C17H12N6, Mr=300.3): C, 67.99; H, 4.03; N, 27.98%;It is real
Actual value: C, 68.00; H, 4.03; N, 27.99%.
Infrared spectrum：IR (pressing potassium bromide troche, cm-1): 1589m, 1566m, 1507m, 1451s, 1413m,
1218s, 1151s, 1118s, 1086s, 1071s, 989m, 847s, 824s, 783s, 736s, 709s, 674m,
627s, 606s, 527s, 503s.
Embodiment 2：
The preparation of more Pyridine Bridges connection organic ligand (L) containing 1,2,4- triazoles and discussion of results
1. compound experiment and post-processing：
By N- (4- pyridyl groups) -2- pyridines-thioamides（21.5 g, 0.1 mol）And Isoniazid（27.4 g,
0.2 mol）With 200 mL n-Butanol solubles, stop heating after being heated to reflux 36 hours, be cooled to room temperature, decompression filters, and uses second
Alcohol washing obtains light yellow solid afterwards three times.With ethyl alcohol recrystallization, white powder product is obtained.With assay balance precise,
It is 44% to calculate yield.
2. result and discussion：
Analytical and testing instrument：
Elemental analysis, C, H, N content, which measure, uses CE-440 (Leemanlabs) type elemental analyser
Infrared spectrum, AVATAR-370 (Nicolet) Fourier infrared spectrograph
Elemental analysis：Theoretical value (C17H12N6, Mr=300.3): C, 67.99; H, 4.03; N, 27.98%;It is real
Actual value: C, 67.28; H, 4.02; N, 28.00%.
Infrared spectrum：IR (pressing potassium bromide troche, cm-1): 1590m, 1566m, 1508m, 1451s, 1413m,
1219s, 1151s, 1118s, 1086s, 1071s, 989m, 848s, 823s, 783s, 736s, 709s, 673m,
627s, 606s, 527s, 503s.
Embodiment 3：
The preparation of more Pyridine Bridges connection organic ligand (L) containing 1,2,4- triazoles and discussion of results
1. compound experiment and post-processing：
By N- (4- pyridyl groups) -2- pyridines-thioamides（21.5 g, 0.1 mol）And Isoniazid（20.6 g,
0.15 mol）With 200 mL n-Butanol solubles, stop heating after being heated to reflux 40 hours, be cooled to room temperature, decompression filters, and uses second
Alcohol washing obtains light yellow solid afterwards three times.With ethyl alcohol recrystallization, white powder product is obtained.With assay balance precise,
It is 42% to calculate yield.
2. result and discussion：
Analytical and testing instrument：
Elemental analysis, C, H, N content, which measure, uses CE-440 (Leemanlabs) type elemental analyser
Infrared spectrum, AVATAR-370 (Nicolet) Fourier infrared spectrograph
Elemental analysis：Theoretical value (C17H12N6, Mr=300.3): C, 67.99; H, 4.03; N, 27.98%;It is real
Actual value: C, 67.98; H, 4.04; N, 27.98%.
Infrared spectrum：IR (pressing potassium bromide troche, cm-1): 1589m, 1567m, 1508m, 1451s, 1413m,
1218s, 1151s, 1118s, 1086s, 1070s, 989m, 848s, 823s, 782s, 736s, 709s, 673m,
627s, 606s, 528s, 503s.
Embodiment 4：
Coordination polymer material [Ag (L) (NO3)](CH3OH)(H2O)2Preparation and discussion of results
1. [Ag (L) (NO3)](CH3OH)(H2O)2Preparation
Under conditions of normal temperature and pressure is protected from light, by the AgNO of 0.1 mmol3It is dissolved in water and is placed in test tube bottom, buffering is added
Layer, then dissolves 0.1 mmol ligand Ls with methanol, and be slowly added drop-wise to AgNO3The upper layer of aqueous solution stands volatilization 3~5
It obtains colourless bulk-shaped monocrystal product.Yield：67%.
2. result and discussion：
Analytical and testing instrument：
Elemental analysis, C, H, N content, which measure, uses CE-440 (Leemanlabs) type elemental analyser
Infrared spectrum, AVATAR-370 (Nicolet) Fourier infrared spectrograph
Powder X-ray Diffractometer, Bruker D8 Advance diffractometers
Elemental analysis：Theoretical value: C, 40.16; H, 3.75; N, 18.22%;Experiment value: C, 40.17; H,
3.76; N, 18.20%.
Infrared spectrum：IR (pressing potassium bromide troche, cm-1): 1642s, 1595m, 1451s, 1380w, 1112m,
983s, 850s, 783s, 709s, 612s, 624 m.
Embodiment 5：
Coordination polymer material [Ag (L) (NO3)](CH3OH)(H2O)2Preparation and discussion of results
1. [Ag (L) (NO3)](CH3OH)(H2O)2Preparation
Under conditions of normal temperature and pressure is protected from light, by the AgNO of 0.2 mmol3It is dissolved in water and is placed in test tube bottom, buffering is added
Layer, then dissolves 0.2 mmol ligand Ls with methanol, and be slowly added drop-wise to AgNO3The upper layer of aqueous solution stands volatilization 3~5
It obtains colourless bulk-shaped monocrystal product.Yield：65%.
2. result and discussion：
Analytical and testing instrument：
Elemental analysis, C, H, N content, which measure, uses CE-440 (Leemanlabs) type elemental analyser
Infrared spectrum, AVATAR-370 (Nicolet) Fourier infrared spectrograph
Powder X-ray Diffractometer, Bruker D8 Advance diffractometers
Elemental analysis：Theoretical value: C, 40.16; H, 3.75; N, 18.22%;Experiment value: C, 40.15; H,
3.75; N, 18.23%.
Infrared spectrum：IR (pressing potassium bromide troche, cm-1): 1643s, 1595m, 1450s, 1380w, 1114m,
983s, 850s, 783s, 709s, 612s, 624 m.
Embodiment 6：
Coordination polymer material [Ag (L) (NO3)](CH3OH)(H2O)2Preparation and discussion of results
1. [Ag (L) (NO3)](CH3OH)(H2O)2Preparation
Under conditions of normal temperature and pressure is protected from light, by the AgNO of 0.5 mmol3It is dissolved in water and is placed in test tube bottom, buffering is added
Layer, then dissolves 0.5 mmol ligand Ls with methanol, and be slowly added drop-wise to AgNO3The upper layer of aqueous solution stands volatilization 3~5
It obtains colourless bulk-shaped monocrystal product.Yield：62%.
2. result and discussion：
Analytical and testing instrument：
Elemental analysis, C, H, N content, which measure, uses CE-440 (Leemanlabs) type elemental analyser
Infrared spectrum, AVATAR-370 (Nicolet) Fourier infrared spectrograph
Powder X-ray Diffractometer, Bruker D8 Advance diffractometers
Elemental analysis：Theoretical value: C, 40.16; H, 3.75; N, 18.22%;Experiment value: C, 40.14; H,
3.76; N, 18.21%.
Infrared spectrum：IR (pressing potassium bromide troche, cm-1): 1643s, 1595m, 1450s, 1380w, 1113m,
984s, 851s, 783s, 709s, 610s, 624 m.
Crystal data：1: C18H20AgN7O6, M = 538.28, monoclinic, space group P21 n, a =
10.015(2) Å, b = 14.505(3) Å, c = 15.454(3) Å, α = γ = 90 o, β= 104.390(3),V = 2174.5(8) Å3, Z = 4, μ= 0.977 mmˉ1, GOF = 1.121, R int = 0.0368, final R
indices [I > 2σ(I)] R 1 = 0.0561 and wR 2 =0.1457。
Application Example 1:
Coordination polymer material [Ag (L) (NO3)](CH3OH)(H2O)2For ReO4 -The enrichment performance of ion：
（1）Obtained crystal prototype in embodiment 4 (0.1 mmol) is immersed in containing potassium perrhenate (0.2 mmol)
Aqueous solution in, be stirred at room temperature.Products therefrom is filtered, washed after 10 hours, be dried in vacuo after it is to be identified.Identification of means is red
External spectrum.
（2）Obtained crystal prototype in embodiment 4 (0.1 mmol) is immersed in containing potassium perrhenate (0.4 mmol)
Aqueous solution in, products therefrom is filtered, washed after being stirred at room temperature 8 hours, be dried in vacuo after it is to be identified.Identification of means is infrared
Spectrum.
The results of FT-IR：Exchange product and former complex infrared spectrum have it is significantly different, in 910 cm–1There is height
The characteristic peak of rehenic acid root, and nitrate anion 1380cm–1Characteristic peak disappear.
ICP test results：The ability that the material adsorbs high rhenium acid group is 0.98 mol/mol.
Result above proves that this material can be used as the enrichment material of high rhenium acid group anion, and under the same conditions can not
Reversible exchange occurs.
Application Example 2:
Coordination polymer material [Ag (L) (NO3)](CH3OH)(H2O)2To ReO4 -Anion is enriched with the selectivity of performance：
(1) obtained crystal prototype in embodiment 4 (0.1 mmol) is immersed in containing tetrafluoroborate（0.2
mmol）In the aqueous solution of high rhenium acid group (0.2 mmol), it is stirred at room temperature.Products therefrom is filtered, washed after 10 hours, very
It is to be identified after sky is dry.Identification of means is infrared spectrum.
The results of FT-IR：There is the characteristic peak of high rhenium acid group but does not have in the infrared spectrum of products therefrom after exchange reaction
There is the characteristic peak of tetrafluoroborate.
(1) obtained crystal prototype in embodiment 4 (0.1 mmol) is immersed in containing perchlorate（0.2 mmol）
In the aqueous solution of high rhenium acid group (0.2 mmol), it is stirred at room temperature.Products therefrom is filtered, washed after 10 hours, vacuum is done
It is to be identified after dry.Identification of means is infrared spectrum.
The results of FT-IR：There is the characteristic peak of high rhenium acid group in the infrared spectrum of products therefrom after exchange reaction, but does not have
Occur the characteristic peak of perchlorate.
Result above proves this material for ReO4 -Ion exchange there is preferable selectivity.
Claims (1)
1. coordination polymer [Ag (L) (NO with Three-dimensional Open skeleton3)](CH3OH)(H2O)2It is cloudy in absorption water meso-perrhenic acid root
The application of ions；The wherein structural formula of L is as follows：
。
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| Title |
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| Anion-directed assembly of two fluorescent Cd(II) coordination polymers with a versatile multidentate N-donor building block 3-(2-pyridyl)-4,5-bis(4-pyridyl)-1,2,4-triazole;Wei Guo等;《Inorganic Chemistry Communications》;20100502;第13卷;863-866 * |
| From N-substituted Thioamides to Symmertrical and Unsymmertrical 3,4,5-trisubstituted 4H-1,2,4-Triazoles: Synthesis and Charaterisation of New Chelating Ligands;Marco H. Klingele等;《Eur. J. Org. Chem.》;20041231;3422-3434 * |
| Solvent-regulated assemblies of silver(I) and cadmium(ii) supramolecular complexes with versatile tripyridyltriazole multidentate ligands;Jian Guo等;《Inorganica Chimica Acta》;20121105;第395卷;212-217 * |
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