CN105503916A - Organic ligand BDPO, metal-organic framework compound for detecting rhodamin B and preparation method and application of metal-organic framework compound - Google Patents

Organic ligand BDPO, metal-organic framework compound for detecting rhodamin B and preparation method and application of metal-organic framework compound Download PDF

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CN105503916A
CN105503916A CN201610025223.2A CN201610025223A CN105503916A CN 105503916 A CN105503916 A CN 105503916A CN 201610025223 A CN201610025223 A CN 201610025223A CN 105503916 A CN105503916 A CN 105503916A
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preparation
bdpo
framework compound
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organic framework
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CN105503916B (en
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江亚沁
云瑞瑞
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Anhui Normal University
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Anhui Normal University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/81—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/17—Systems in which incident light is modified in accordance with the properties of the material investigated
    • G01N21/25—Colour; Spectral properties, i.e. comparison of effect of material on the light at two or more different wavelengths or wavelength bands
    • G01N21/31—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry

Abstract

The invention discloses an organic ligand BDPO, a metal-organic framework compound for detecting rhodamin B and a preparation method and application of the metal-organic framework compound. The preparation method comprises the step that under the existence of water, nitric acid and organic solvent, yttrium salt and the organic ligand BDPO with the structure shown in a formula (I) are subjected to a coordination reaction to prepare the metal-organic framework compound. The metal-organic framework compound prepared through the method and the organic ligand BDPO has the efficient sensitivity on rhodamin B detection.

Description

Organic ligand BDPO, for metal organic framework compound detecting rhodamine B and its preparation method and application
Technical field
The present invention relates to metal organic framework compound, particularly, relate to organic ligand BDPO, for metal organic framework compound detecting rhodamine B and preparation method thereof.
Background technology
Along with the develop rapidly of world economy, the organic dye being widely used in the industry such as textile printing and dyeing, makeup discharges the environmental pollution caused has become global environmental problem, and the environmental hazard that this problem is brought in China is particularly serious.Organic dye is all poisonous and carcinogenic usually, and due to its biological activity difference and complex structure, organic dye is just difficult to degraded once be discharged into occurring in nature.If do not detect accurately polluted source and process timely, then can cause great harm to the health of people.
Metal organic framework compound is the porous material of the inorganic-organic hybridization that a class newly-developed gets up, it has the application potential of varied and adjustable constructional feature and each side, and the research thus in catalysis, separation, atmosphere storage and carbon dioxide capture etc. has very big breakthrough.Especially, in atmosphere storage, researchers both domestic and external have carried out deep probing into, and obtain a series of progress.At home, the raw teach problem group of the Guo Guang of Peking University from the layer with photocatalytic properties of metal organic framework compound in the face of the process of organic pollutant is probed into.A kind of zinc metal organic framework compound of seminar's synthesis that Zhengzhou University Zang Shuanquan teaches can fast and effectively adsorb toluidine blue.The Liu Fu minister teach problem group research of Institutes Of Technology Of Tianjin obtains a series of metal organic framework compound and can be separated different organic dye.But for the research but relatively fresh rare report of the dye efficient high-sensitivity detection performance of metal organic framework compound, simultaneously about organic dye context of detection, the majority in this area is nano material.
Summary of the invention
The object of this invention is to provide a kind of organic ligand BDPO, for metal organic framework compound detecting rhodamine B and its preparation method and application, the detection of metal organic framework compound to rhodamine B obtained by the method and machine part BDPO has efficient sensitivity.
To achieve these goals, the invention provides a kind of preparation method of the metal organic framework compound for detecting rhodamine B, this preparation method is: under the existence of water, nitric acid and organic solvent, yttrium salt and the organic ligand BDPO such as formula structure (I) Suo Shi are carried out coordination reaction with obtained metal organic framework compound
Present invention provides a kind of metal organic framework compound for detecting rhodamine B, this metal organic framework compound is prepared from by above-mentioned method.
Present invention also offers a kind of above-mentioned metal organic framework compound and detect the application in rhodamine B.
Invention further provides a kind of organic ligand BDPO, the structure of this organic ligand BDPO such as formula shown in (I),
The present invention still further provides the preparation method of a kind of above-mentioned organic ligand BDPO, and this preparation method is: in presence of organic solvent, and p-phthaloyl chloride and the amino m-phthalic acid of 5-are carried out contact reacts with obtained organic ligand BDPO.
Pass through technique scheme, the present invention uses crystal engineering principle, select to adopt the rare earth metal yttrium of the 4f electron structure with uniqueness and organic ligand BDPO to carry out coordination reaction, synthesis performance is unique, the rare earth metal organic frame compound of novel structure (as Figure 1-4, due to Y (III) and with organic ligand BDPO, there are two kinds of coordination modes of Fig. 1 or Fig. 2, namely the title complex of these the two kinds of configurations of a and b in Fig. 4 is defined, skeleton construction c is formed between a and a, skeleton construction d is formed between b and b, last c and d is self-assembled into framework Verbindung).And rare earth metal organic frame compound is applied in the efficient and sensible detection to organic dye rhodamine B by this, wherein, detectability can reach ppm level, thus makes this rare earth metal organic frame compound have appreciable using value in sewage disposal and environmental improvement.
Other features and advantages of the present invention are described in detail in embodiment part subsequently.
Accompanying drawing explanation
Accompanying drawing is used to provide a further understanding of the present invention, and forms a part for specification sheets, is used from explanation the present invention, but is not construed as limiting the invention with embodiment one below.In the accompanying drawings:
Fig. 1 is the structural representation of the coordination mode I of Y (III) and organic ligand BDPO;
Fig. 2 is the structural representation of the coordination mode II of Y (III) and organic ligand BDPO;
Fig. 3 is the structural representation of asymmetric cell in organic frame compound crystal provided by the invention;
Fig. 4 is the 2D channel architecture schematic diagram inventing the organic frame compound provided;
Fig. 5 is the three-dimensional crystalline structure inventing the organic frame compound provided;
Fig. 6 is application examples 1 medium ultraviolet-visible absorption spectra figure.
Embodiment
Below the specific embodiment of the present invention is described in detail.Should be understood that, embodiment described herein, only for instruction and explanation of the present invention, is not limited to the present invention.
The invention provides a kind of preparation method of the metal organic framework compound for detecting rhodamine B, this preparation method is: under the existence of water, nitric acid and organic solvent, yttrium salt and the organic ligand BDPO such as formula structure (I) Suo Shi are carried out coordination reaction with obtained metal organic framework compound
In the preparation method of metal organic framework compound provided by the invention, the consumption of each material can be selected in wide scope, but in order to improve productive rate, preferably, relative to the yttrium salt of 0.1mmol, the consumption of organic ligand BDPO is 0.01-0.03mmol, and the consumption of organic solvent is 1-3ml, the consumption of water is 0.2-0.5ml, and the consumption of nitric acid is 30-50 μ L.
In the preparation method of metal organic framework compound provided by the invention, the condition of coordination reaction can be selected in wide scope, but in order to improve productive rate and reaction efficiency, preferably, coordination reaction at least meets the following conditions: temperature of reaction is 70-90 DEG C, and the reaction times is 40-55h.
In the preparation method of metal organic framework compound provided by the invention, the kind of organic solvent and yttrium salt can be selected in wide scope, but in order to taking cost into account improve productive rate and reaction efficiency simultaneously, preferably, organic solvent is DMF, N,N-dimethylacetamide and N, one or more in N-diethylformamide, yttrium salt is six nitric hydrate yttriums.
In the preparation method of metal organic framework compound provided by the invention, the order of addition of material can be selected in wide scope, but in order to improve productive rate and reaction efficiency, preferably, the filler order of preparation method is: first organic solvent, yttrium salt are mixed with organic ligand BDPO, and then add water and nitric acid.
Present invention provides a kind of metal organic framework compound for detecting rhodamine B, this metal organic framework compound is prepared from by above-mentioned method.
Present invention also offers a kind of above-mentioned metal organic framework compound and detect the application in rhodamine B.
Invention further provides a kind of organic ligand BDPO, the structure of this organic ligand BDPO such as formula shown in (I),
The present invention still further provides the preparation method of a kind of above-mentioned organic ligand BDPO, and this preparation method is: in presence of organic solvent, and p-phthaloyl chloride and the amino m-phthalic acid of 5-are carried out contact reacts with obtained organic ligand BDPO.
In the preparation method of organic ligand BDPO provided by the invention, the consumption of each material can be selected in wide scope, but in order to improve productive rate, preferably, relative to the p-phthaloyl chloride of 1mmol, the consumption of the amino m-phthalic acid of 5-is 2-3mmol, and the consumption of organic solvent is 30-35ml.
In the preparation method of organic ligand BDPO provided by the invention, catalytic condition can be selected in wide scope, but in order to improve productive rate, preferably, contact reacts carries out 20-30h under condition of ice bath.
In the preparation method of organic ligand BDPO provided by the invention, the kind of organic solvent can be selected in wide scope, but taking cost into account, preferably, organic solvent is N,N-dimethylacetamide, N, one or more in dinethylformamide and N, N-diethylformamide.
Below will be described the present invention by embodiment.In following examples, p-phthaloyl chloride is the commercially available product of Beijing lark prestige company, and the amino m-phthalic acid of 5-is the commercially available product of Tokyo Ren Cheng Industrial Co., Ltd, and six nitric hydrate yttriums are the commercially available product of traditional Chinese medicines company.
Preparation example 1
By amino to p-phthaloyl chloride (1mmol) and 5-m-phthalic acid (2.2mmol) N,N-dimethylacetamide (30-35ml) is mixed be incorporated in condition of ice bath under react 24h and obtain organic ligand BDPO.
The nuclear magnetic resonance analyser being AV300 type (AVANCE system) by the trade mark of Bruker company of Switzerland detects above-mentioned organic ligand BDPO, and this organic ligand BDPO nucleus magnetic hydrogen spectrum detect parameters is: 1hNMR (DMSO-d6, δ ppm): 13.363 (broadpeak, COOH), 10.972 (s, 3H, CONH), 8.855 (s, 3H, ArH), 8.745 (s, 6H, ArH), 8.269 (s, 3H, ArH); MP:>300 DEG C.
Embodiment 1
By above-mentioned organic ligand BDPO (0.02mmol, 10.0mg) and Y (NO 3) 36H 2o (0.1mmol, 38.3mg) be dissolved in N, in dinethylformamide (2.0ml), add distilled water (0.3ml) and nitric acid (40 μ l) again, then the mixture prepared is encapsulated in phial, react 48h under the environment of constant temperature 80 DEG C after, collect the clear crystal obtained, and wash repeatedly with DMF, obtain metal organic framework compound 0.012g.
Detect this metal organic framework compound, ultimate analysis (C, H and N) completes in Perkin-Elmer240 elemental analyser.IR spectrum is at 4000-400cm with KBr compressing tablet -1obtain and be recorded on VECTOR22 spectrograph in scope. 1h NMR (Nuclear Magnetic Resonance) spectrum is recorded in tetramethylsilane at ambient temperature as in BrukerDRX – 500 spectrograph of internal standard.Thermogravimetric analysis (TGA) is in nitrogen atmosphere (100ml/min), use 2960SDT thermogravimetric analyzer to carry out, and heating rate is 5 DEG C/min.The data of powder x-ray diffraction (PXRD) be by BrukeraxsD8AdvanceX x ray diffractometer x use under 2 θ scope 5-30 ° conditions copper target K α radiation ( ), the sweep velocity often spent with 0.02 second under room temperature is collected.
Y (NO 3) 36H 2the solvent thermal reaction of O and part carries out in DMF (DMF), and adds deionized water and nitric acid, obtains and belongs to the colourless bulk crystals [Y that centrosymmetric oblique system spacer is C2/c 2(L) 1.5(DMF) 2] 2DMF (1).(in fig 1 and 2, central atom is Y, and larger ellipsoid tracer atom is O, and less ellipsoid tracer atom is C as illustrated in fig. 1-3; In figure 3, central atom is Y, and maximum ellipsoid tracer atom is C, and larger ellipsoid tracer atom is O, minimum ellipsoid tracer atom is N), Fig. 1's is the ligand polymer structure of the three-dimensional that the part that is connected with 6-of a kind of Y node be connected based on 4-with 5-is formed.The stoichiometric ratio that the asymmetric cell of Fig. 1 is shown as in this metal organic framework compound structure Y (III): L is 2:1.5.It is all eight-coordinate that the X-ray single crystal diffraction of Fig. 1 discloses each Y (III) center, wherein has six Sauerstoffatoms to come from different parts, and another two Sauerstoffatoms come from DMF.Sauerstoffatom in carboxyl is with chelating and bridging two kinds of different configurations and Y (III) coordination.
In the structure of fig. 1, double-core Y (III) is connected by Sauerstoffatom bridging, and two dinuclear metal bunch are connected by the m-phthalic acid in part.One-dimensional chain is made up of metal cluster and m-phthalic acid.The part of these one-dimensional chains configuration different from two kinds forms 2D passage jointly, as shown in Figure 4.
In order to synthesize three dimensional skeletal structure, part reverses becomes cross configuration.We can see from Fig. 5, and part has two class configurations, and a kind of is plane configuration and another kind is cross configuration, and this gives the credit to the handiness of part.Obviously, define a two dimensional surface at the Y of two carboxyl coordinations (III) that has of part, the other side has the Y of two carboxyl coordinations (III) to be connected to two planes as a columnar structure simultaneously.Finally, whole skeleton is made up of the two-dimensional channel containing DMF solvent in structure.
For the ease of understanding, part is reduced to the node that a kind of 6-connects by us, and Y (III) is reduced to 4-, the node that 5-connects, its topological framework can be described as one (4,5 thus, 6,6) reticulation of-connection, its stoichiometry is than being (4-c) 2(5-c) 2(6-c) 3.TOPOS program computation is used to obtain the topological framework point of 1 symbol is (4 5.6 8.8 2) 3(4 5.6) 2(4 8.6 2) 2.
Embodiment 2
Carry out obtained metal organic framework compound 0.006g according to the method for embodiment 1, the consumption unlike organic ligand BDPO is 0.01mmol.
Embodiment 3
Carry out obtained metal organic framework compound 0.017g according to the method for embodiment 1, the consumption unlike organic ligand BDPO is 0.03mmol.
Embodiment 4
Carry out obtained metal organic framework compound 0.010g according to the method for embodiment 1, the consumption unlike nitric acid is 30 μ l.
Embodiment 5
Carry out obtained metal organic framework compound 0.009g according to the method for embodiment 1, the consumption unlike nitric acid is 50 μ l.
Embodiment 6
Carrying out obtained metal organic framework compound 0.009g according to the method for embodiment 1, is 70 DEG C unlike temperature of reaction.
Embodiment 7
Carrying out obtained metal organic framework compound 0.010g according to the method for embodiment 1, is 90 DEG C unlike temperature of reaction.
Embodiment 8
Carry out obtained metal organic framework compound 0.011g according to the method for embodiment 1, the consumption unlike water is 0.2ml.
Embodiment 9
Carry out obtained metal organic framework compound 0.009g according to the method for embodiment 1, the consumption unlike water is 0.5ml.
Application examples 1
(concentration of rhodamine B is 2 × 10 to the DMF aqueous solution being transferred to by above-mentioned obtained metal organic framework compound crystal (20mg) containing rhodamine B -12mol/L) in, the ultraviolet-visible near infrared spectrometer of Japanese Shimadzu Corporation trade mark U-4100 is adopted to detect, detected result is shown in that Fig. 5 (wherein, RB refers to the uv-visible absorption spectra of rhodamine B solution, baseline representative be the uv-visible absorption spectra of water, RB+Y-BDPO refers to the uv-visible absorption spectra of rhodamine B solution and the mixed system of metal organic framework compound), as shown in Figure 5, the detection of metal organic framework compound provided by the invention to rhodamine B has excellent sensitivity.
More than describe the preferred embodiment of the present invention in detail; but the present invention is not limited to the detail in above-mentioned embodiment, within the scope of technical conceive of the present invention; can carry out multiple simple variant to technical scheme of the present invention, these simple variant all belong to protection scope of the present invention.
It should be noted that in addition, each concrete technical characteristic described in above-mentioned embodiment, in reconcilable situation, can be combined by any suitable mode, in order to avoid unnecessary repetition, the present invention illustrates no longer separately to various possible array mode.
In addition, also can carry out arbitrary combination between various different embodiment of the present invention, as long as it is without prejudice to thought of the present invention, it should be considered as content disclosed in this invention equally.

Claims (10)

1. one kind for detecting the preparation method of the metal organic framework compound of rhodamine B, it is characterized in that, described preparation method is: under the existence of water, nitric acid and organic solvent, yttrium salt and the organic ligand BDPO such as formula structure (I) Suo Shi are carried out coordination reaction with obtained described metal organic framework compound
2. preparation method according to claim 1, wherein, relative to the yttrium salt of 0.1mmol, the consumption of described organic ligand BDPO is 0.01-0.03mmol, the consumption of described organic solvent is 1-3ml, and the consumption of described water is 0.2-0.5ml, and the consumption of described nitric acid is 30-50 μ L.
3. preparation method according to claim 2, wherein, described coordination reaction at least meets the following conditions: temperature of reaction is 70-90 DEG C, and the reaction times is 40-55h.
4. the preparation method according to claim 1-3 any one, wherein, described organic solvent is one or more in DMF, N,N-dimethylacetamide and N, N-diethylformamide, and described yttrium salt is six nitric hydrate yttriums.
5. preparation method according to claim 4, wherein, the filler order of described preparation method is: first described organic solvent, yttrium salt are mixed with organic ligand BDPO, and then add described water and nitric acid.
6. for detecting a metal organic framework compound for rhodamine B, it is characterized in that, described metal organic framework compound is prepared from by the method in claim 1-5 described in any one.
7. a metal organic framework compound as claimed in claim 6 is detecting the application in rhodamine B.
8. an organic ligand BDPO, is characterized in that, the structure of described organic ligand BDPO such as formula shown in (I),
9. a preparation method of organic ligand BDPO as claimed in claim 8, is characterized in that, described preparation method is: in presence of organic solvent, and p-phthaloyl chloride and the amino m-phthalic acid of 5-are carried out contact reacts with obtained described organic ligand BDPO.
10. preparation method according to claim 9, wherein, relative to the p-phthaloyl chloride of 1mmol, the consumption of the amino m-phthalic acid of described 5-is 2-3mmol, and the consumption of described organic solvent is 30-35ml;
Preferably, described contact reacts carries out 20-30h under condition of ice bath;
More preferably, described organic solvent is one or more in N,N-dimethylacetamide, N, N-diethylformamide and DMF.
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CN104804741A (en) * 2015-03-31 2015-07-29 复旦大学 Single-emission up-conversion nano fluorescent probe and synthetic method thereof
CN105153207A (en) * 2015-09-23 2015-12-16 辽宁大学 Porous rare-earth-cluster metal organic anion framework and preparation method and application thereof
CN105241858A (en) * 2015-10-20 2016-01-13 天津师范大学 Method for detecting dye rhodamine B through upconversion nanometer particles

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