CN110885449A - Three-dimensional cadmium complex and preparation thereof, and application of three-dimensional cadmium complex, fluorescent probe and photodegradation catalyst - Google Patents
Three-dimensional cadmium complex and preparation thereof, and application of three-dimensional cadmium complex, fluorescent probe and photodegradation catalyst Download PDFInfo
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- CN110885449A CN110885449A CN201811104243.4A CN201811104243A CN110885449A CN 110885449 A CN110885449 A CN 110885449A CN 201811104243 A CN201811104243 A CN 201811104243A CN 110885449 A CN110885449 A CN 110885449A
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- 238000002360 preparation method Methods 0.000 title abstract description 7
- 238000010668 complexation reaction Methods 0.000 title description 2
- NXFQHRVNIOXGAQ-YCRREMRBSA-N nitrofurantoin Chemical compound O1C([N+](=O)[O-])=CC=C1\C=N\N1C(=O)NC(=O)C1 NXFQHRVNIOXGAQ-YCRREMRBSA-N 0.000 claims abstract description 24
- 229960000564 nitrofurantoin Drugs 0.000 claims abstract description 24
- IAIWVQXQOWNYOU-FPYGCLRLSA-N nitrofural Chemical compound NC(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-FPYGCLRLSA-N 0.000 claims abstract description 23
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229940043267 rhodamine b Drugs 0.000 claims abstract description 21
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- RBTBFTRPCNLSDE-UHFFFAOYSA-N 3,7-bis(dimethylamino)phenothiazin-5-ium Chemical compound C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 RBTBFTRPCNLSDE-UHFFFAOYSA-N 0.000 claims abstract description 19
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- 239000000126 substance Substances 0.000 claims abstract description 6
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Abstract
The invention provides a preparation method of a cadmium metal complex and application of the cadmium metal complex in a fluorescent probe and a photodegradation catalyst. The chemical formula of the complex is [ Cd (L) (H)2O)·5H2O]n(ii) a Wherein H2L ═ 1, 1 '- (4-carboxyphenyl) -2, 2' -biimidazole. The cadmium metal complex is formed by passing cadmium ions through L2‑The ligand self-assembles to form a three-dimensional structure. The cadmium complex is antibiotic to ferric ion, dichromate ionThe furacilin and the nitrofurantoin show obvious fluorescence quenching effect, can be used as fluorescent probes of the furacilin and the nitrofurantoin, and have potential application value in the fields of environmental monitoring and life science. In addition, the cadmium complex has the properties of stably and efficiently catalyzing photodegradation dyes: under the condition of visible light, the methylene blue, the methyl orange and the rhodamine B are basically and completely degraded within 60 minutes, are easy to separate and can be recycled for multiple times.
Description
Statement regarding sponsoring research or development: the invention is carried out under the subsidy of the policy guidance class plan (obstetric and research cooperation) of Jiangsu province, namely a prospective combined research project (Grant No. BY2016066-08).
Technical Field
The invention belongs to the technical field of organic synthesis and metal organic chemistry, and particularly relates to a preparation method of a three-dimensional cadmium complex taking 1, 1 '- (4-carboxyphenyl) -2, 2' -biimidazole as a ligand and a three-dimensional cadmium complex taken as ferric ion (Fe)3+) Dichromate ion (Cr)2O7 2-) Furacilin (NZF) and Nitrofurantoin (NFT) antibiotic fluorescent probes and can effectively degrade cadmium complexes of Methylene Blue (MB), rhodamine B (RhB) and Methyl Orange (MO) dyes.
Background
Compared with the traditional luminescent materials, the complex fluorescent material attracts much attention because of having high chemical stability of inorganic materials and high quantum yield of organic materials. The fluorescence property of the complex is influenced by factors such as the electronic configuration and energy level of metal ions, the coordination configuration and coordination environment, the ligand and external conditions such as solvent (solution fluorescence), temperature and the like. Particularly, the complexes have pore channels, bare metal sites and active organic groups with Lewis acids or basic sites in the structure, can effectively perform host-guest interaction with guest molecules (including anions, metal cations and organic small molecules), and directly reflect the action result in the fluorescence change of the substance, so that the complexes have good application values in the aspects of organic matter detection, metal ion detection, temperature probes, pH probes, active probes and the like. A series of fluorescent probe complexes have been reported, but there are fewer fluorescent probe complexes capable of simultaneously detecting multiple guest molecules.
The presence of metal ions is closely related to the life of modern human beings: on one hand, with the rapid development of modern industry, the environmental pollution problems such as mining, industrial waste gas and waste water discharge become more serious, and heavy metal ions enter into organisms to cause chronic poisoning of the organisms. On the other hand, metal ions are also indispensable constituent elements for living beings and the human body. Therefore, it is very important to detect metal ions quickly, conveniently and accurately.
Iron is a trace transition metal element in organisms, participates in a plurality of enzymes and components of an immune system in a human body, and is also a main component of hemoglobin, and a plurality of diseases are caused by insufficient or excessive iron element in the body, so that the health of the human body is influenced. However, if the iron content in the human body is excessive, the structure of the human organ is changed, and the disease is caused; such as hepatic fibrosis, serious patients can be life-threatening. Chromium is one of the trace elements necessary for human beings and is also one of the heavy metal pollutants. Chromium in nature generally exists in three-valence and six-valence forms, but the toxicity of the chromium is greatly different, and the toxicity of the six-valence chromium is 100 times higher than that of the three-valence chromium, is a highly toxic environmental pollutant, easily enters human cells, damages internal organs and DNA such as liver and kidney, accumulates in human body, has carcinogenicity, and may induce gene mutation. Therefore, it is very important to detect ferric ions and dichromate ions quickly, conveniently and accurately.
Antibiotics are, colloquially, drugs used to treat various non-viral infections. Furacilin (NZF) is an artificially synthesized antibacterial drug, which can interfere the early stage of bacterial glycometabolism, cause bacterial metabolic disturbance and death, has a wide antibacterial spectrum, can inhibit general bacteria in vitro, can kill bacteria at a high concentration, can treat body surface infection and skin diseases by external washing or wet dressing, but the residue of the furacilin in animal-derived food can be transmitted to human beings through a food chain, can cause various diseases after being taken for a long time, and has side effects of carcinogenesis, teratogenesis and the like on the human bodies. Nitrofurantoin (NFT) is a national basic drug, has a broad-spectrum antibacterial effect, and can effectively kill gram-positive bacteria and gram-negative bacteria infected by the lower urinary tract. The traditional Chinese medicine composition is mainly used for treating acute lower urinary tract infection, chronic bacteriuria and recurrent chronic urinary tract infection caused by sensitive bacteria clinically. Adverse reactions to nitrofurantoin involve multiple organ systems, including the digestive system: nausea, vomiting, diarrhea, and the like; a respiratory system: acute pneumonia, pulmonary interstitial fibrosis, etc.; the nervous system: trigeminal neuralgia, peripheral neuropathy, and blood system: hemolysis, chronic hemolytic anemia; systemic hypersensitivity reaction: rash, fever, jaundice, liver damage, etc. The clinical use of nitrofurantoin tablets has been banned in foreign countries such as the united states, and concerns and precautions for safety may be raised. For the reasons, the selective fluorescence recognition of nitrofurazone and nitrofurantoin is very valuable.
In addition, the rapid development of industry brings about a growing problem of ecological environment, and the living environment of human beings is continuously destroyed, so that the problem of water pollution is getting worse. At present, the main source of water pollution in China is industrial wastewater, wherein the proportion of printing and dyeing wastewater in the industrial wastewater exceeds 35%. The printing and dyeing wastewater has the characteristics of large wastewater quantity, high chroma, high toxicity, complex water quality and the like, and belongs to high-concentration degradation-resistant organic wastewater. The dyes such as Methylene Blue (MB), Methyl Orange (MO), rhodamine B (RhB) and the like are extremely harmful in water, not only seriously harm the ecological balance of rivers and oceans, but also enter human bodies through skin absorption, cause headache and vomiting, and even cause irreversible damage to various organs and even cause cancer. Therefore, the efficient treatment of dye pollutants in water is an important issue.
The traditional water treatment process is continuously reformed due to a series of defects of easy generation of secondary pollution, high energy consumption, low efficiency and the like, and the reformation of the simple traditional treatment process is gradually changed into the research and development of new materials for water treatment. The method for degrading dye wastewater by using the environmental purification material to catalyze light can degrade a plurality of complex macromolecules which are difficult to be biodegraded, and attracts more and more attention in the field of dye wastewater treatment. Therefore, it is an important challenge to design an environment purification material having excellent photocatalytic properties, which is environment-friendly in synthesis, simple in synthesis method.
Compared with the traditional semiconductor materials for photodegradation, the complex has many advantages in the aspect of photodegradation of dyes: (1) the precision of the crystal structure is beneficial to researching the relationship between the structure and the property of the ligand photodegradation dye; (2) the tunable active sites promote the ligand to photodegrade the dye, and the solar energy is efficiently utilized; (3) the porosity and the larger specific surface area of the complex can allow dye molecules to rapidly pass through a channel, which is very effective for improving the efficiency of photocatalytic degradation; (4) the interaction of the metal ions of the complex and the ligand can effectively separate photoproduction electrons and holes, thereby improving the photocatalytic activity. Therefore, the complex has high photocatalytic activity and chemical stability, and the synthesis method is simple, so that the complex is an ideal catalyst for photoreaction.
1, 1 '- (4-carboxyphenyl) -2, 2' -biimidazole is a bridging ligand with stronger coordination capacity: two carboxylic acid groups are arranged at two ends of the ligand, and two benzene rings are connected through biimidazole, so that the synthesis of the complex is facilitated; it can be partially or completely deprotonated, allows different coordination models with metal ions, and facilitates the synthesis of metal complexes with different dimensions, which is a crucial step in the completion of device formation.
The invention belongs to the technical field of organic synthesis and metal organic chemistry, and relates to synthesis of a three-dimensional cadmium metal fluorescent complex, in particular to synthesis of a cadmium coordination polymer taking 1, 1 '- (4-carboxyphenyl) -2, 2' -biimidazole as a ligand and application of the cadmium coordination polymer as a fluorescent probe and a photodegradation catalyst. The invention respectively adopts divalent cadmium ions as a main body and 1, 1 '- (4-carboxyphenyl) -2, 2' -biimidazole as a ligand, researches the influence of different solvent molecules on the fluorescence performance of a metal complex, shows obvious fluorescence quenching effect on trivalent iron ions, dichromate ions and antibiotics by the cadmium fluorescent complex with a three-dimensional structure, can be applied to detection and analysis research of metal ions and antibiotic molecules as a fluorescent probe material, and has wide application prospect. In addition, in the invention, the complex synthesized by the method has obvious photodegradability properties on methylene blue, methyl orange and rhodamine B dye: under the condition of visible light, the methylene blue, the methyl orange and the rhodamine B dye are basically and completely degraded within 60 minutes, are easy to separate and are recycled for multiple times, and the catalytic efficiency is basically kept unchanged.
In summary, there are a number of reports of complexes with fluorescence and photodegradation, respectively, but with Fe3+、Cr2O7 2-Very few reports have been made of complexes that respond to, and have significant photodegradability properties in, NZF and NFT. In the invention, the synthesized metal complex has the advantages of low cost, high efficiency, good reproducibility, sensitive detection, easy separation and high yield, and Fe is used as a metal complex3+、Cr2O7 2-The NZF and NFT detection and the degradation of methylene blue, methyl orange and rhodamine B dyes have a wide application prospect.
Disclosure of Invention
The invention aims to provide a three-dimensional cadmium complex which is used as a ferric ion, dichromate ion, nitrofural and nitrofurantoin fluorescent probe and can effectively catalyze and degrade methyl blue, methyl orange and rhodamine B dyes and a preparation method thereof. The invention selects 1, 1 '- (4-carboxyl phenyl) -2, 2' -biimidazole ligand and cadmium nitrate tetrahydrate to construct cadmium coordination polymer. The compound has a fluorescent recognition function on ferric ions, dichromate ions, antibiotic nitrofural and antibiotic nitrofural, can detect the existence of trace ferric ions, dichromate ions, antibiotic nitrofural and nitrofural in an aqueous solution, can efficiently degrade methylene blue, methyl orange and rhodamine B organic dyes, and can ensure excellent catalytic activity and repeatability. The compound has the advantages of simple synthesis process, low cost, high efficiency, good reproducibility, sensitive detection, easy separation and high yield, can be applied to industrial production, and has potential application prospects in the fields of environmental monitoring, life science and pollutant degradation.
The chemical formula of the cadmium complex used as a ferric ion, dichromate ion, antibiotic nitrofurazone and nitrofurantoin fluorescent probe and a methylene blue, methyl orange and rhodamine B photodegradation catalyst related by the invention is as follows: [ Cd (L) (H)2O)·5H2O]nWherein H is2L ═ 1, 1 '- (4-carboxyphenyl) -2, 2' -biimidazole. H2The structural formula of L is as follows:
the structure of the three-dimensional cadmium complex used as a ferric ion, dichromate ion, antibiotic nitrofural and nitrofurantoin fluorescent probe and a methylene blue, methyl orange and rhodamine B photodegradation catalyst related by the invention is shown in figure 1(a), and the basic structural parameters are as follows:
crystals of the cadmium complexes of the inventionIn the monoclinic system, space group is P21And c, unit cell parameters are as follows:
α gamma 90 deg. and β gamma 114.354(5 deg. the central ion cadmium is in a hexa-coordinated octahedral configuration, and the cadmium ion is coordinated with 1, 1 '- (4-carboxyphenyl) -2, 2' -biimidazole carboxyl oxygen atom and imidazole nitrogen atom to form a complex three-dimensional cadmium coordination polymer, as shown in fig. 1 (b).
The preparation method of the cadmium complex comprises the following steps:
(1) 14.8mg of cadmium nitrate tetrahydrate (Cd (NO)3)2·4H2O), 18.7mg of 1, 1 '- (4-carboxyphenyl) -2, 2' -biimidazole (H)2L) is put into a polytetrafluoroethylene inner container of a hydrothermal 25mL reaction kettle to be mixed, and then the concentration is added to be 0.15 mol.L-1Adjusting the pH value of the HCl solution to 1.2, adjusting the volume of the adjusted aqueous solution to 10mL, and stirring at normal temperature for 30 minutes to obtain a mixed solution;
(2) drying the mixed solution at 120 ℃ for 72 hours, taking out the product, and separating the solid;
(3) the solid was washed three times with ethanol to give colorless transparent bulk crystals.
Further, the invention provides application of the cadmium complex serving as a ferric ion, dichromate ion, antibiotic nitrofural and nitrofurantoin fluorescent probe, and the cadmium complex is used for monitoring the ferric ion, the dichromate ion, the nitrofural and the nitrofurantoin in environment and organisms. In addition, the invention also provides application of the cadmium complex in removing methylene blue, methyl orange and rhodamine B dyes in water by catalytic photodegradation, and is used for treating methylene blue, methyl orange and rhodamine B dye wastewater in natural water.
The invention has the advantages that: the preparation method has the advantages of simple process, high yield, easy separation, good reproducibility, high sensitivity, good catalytic efficiency and high yield, can obtain a single crystal form and a high-purity crystal material, and is easy for industrial production; the product has a fluorescent recognition function on ferric ions, dichromate ions, nitrofural and nitrofural, can be used for detecting trace ferric ions, dichromate ions, nitrofural and nitrofural in an aqueous solution, and has the advantages of qualitative, rapid, sensitive, high-efficiency, simple and convenient operation and the like compared with the traditional detection method; the product can effectively catalyze and degrade methylene blue, methyl orange and rhodamine B under visible light, and can be recycled for many times, and the catalytic efficiency is basically kept unchanged.
Brief description of the drawings
FIG. 1(a) is a crystal structure diagram of a cadmium complex of the present invention; FIG. 1(b) is a three-dimensional structural diagram of a cadmium complex of the present invention.
FIG. 2 is a solid fluorescence image of the cadmium complex of the present invention.
FIG. 3 is a graph of fluorescence intensity of cadmium complex of the present invention for different solvents.
FIG. 4(a) is a graph of the fluorescence emission intensity of cadmium complexes of the present invention for different metal solutions; FIG. 4(b) is a fluorescence intensity diagram and a fluorescence quenching fitting diagram of the cadmium complex of the present invention for solutions of ferric ions of different concentrations.
FIG. 5(a) is a graph of the fluorescence emission intensity of cadmium complexes of the present invention for different anion solutions; FIG. 5(b) is a fluorescence intensity plot and a fluorescence quenching fitting plot of the cadmium complex of the present invention against different concentrations of dichromate ion solutions.
FIG. 6(a) is a graph of the fluorescence emission intensity of cadmium complexes of the present invention for different antibiotic solutions; FIG. 6(b) is a fluorescence emission intensity diagram and a fluorescence quenching fitting diagram of the cadmium complex of the present invention for furacilin solutions of different concentrations.
FIG. 7 is a diagram of the photocatalytic degradation of the cadmium complex of the present invention to methylene blue.
FIG. 8 is a diagram of the photocatalytic degradation of cadmium complex to methyl orange according to the present invention.
FIG. 9 is a diagram showing the photocatalytic degradation of rhodamine B by the cadmium complex of the present invention.
FIG. 10 is a photo-catalytic cyclic degradation diagram of the cadmium complex of the present invention for rhodamine B.
Detailed Description
In order to better understand the invention, the following description is further provided in connection with the examples, but the invention is not limited to the following examples. The starting materials of the present invention are all commercially available.
The starting materials used in the examples are all commercially available. Cadmium nitrate tetrahydrate, analytically pure, national pharmaceutical group: 1, 1 '- (4-carboxyphenyl) -2, 2' -biimidazole, chemostat.
Example 1 synthesis of the complex:
15.4mg of cadmium nitrate tetrahydrate (Cd (NO)3)2·4H2O), 18.71mg of 1, 1 '- (4-carboxyphenyl) -2, 2' -biimidazole (H)2L) is dissolved in 10mL of water, stirred for half an hour, transferred to a polytetrafluoroethylene liner of a 25mL hydrothermal reaction kettle, reacted for 72 hours at the temperature of 120 ℃, and the obtained product is washed with ethanol for three times (2 mL/time) to obtain colorless transparent blocky crystals. The yield was 52.5% based on metal Cd.
Example 2 structural characterization of the complex:
selecting crystal with size of 0.35 × 0.15 × 0.12mm under 296(2) K with Bruker Smart CCD X-ray single crystal diffractometer, collecting diffraction points by omega/2 theta scanning with MoK α ray (λ 0.07107nm) obtained by monochromating graphite as incident radiation source, refining unit cell parameters by least square method, performing absorption correction on the collected data by SADABS program, directly solving out complex structure, refining non-hydrogen atom coordinates and anisotropic temperature factor by full matrix least square method, and performing total calculation by SHELXTL program, wherein detailed crystallographic parameters are listed in Table 1, [ Cd L ] (H L) ((H-Cd L))2O)·5H2O]nThe crystal structure diagram and the three-dimensional structure diagram of (a) are shown in fig. 1(a) and fig. 1 (b).
TABLE 1 crystallographic data for the complexes
Fluorescence properties of the complex of example 3:
and (3) testing the fluorescence property of the complex at room temperature by using an LS-55 type fluorescence spectrometer. FIG. 2 is a solid fluorescence diagram of the cadmium complex prepared in example 1, which shows that the material has strong fluorescence property. As shown in FIG. 3, the complex shows strong luminescence property in aqueous solution.
As can be seen from FIG. 4(a), in the selected aqueous solution of metal ions, the fluorescence intensity of the cadmium complex prepared in example 1 shows dependence on metal ions, and on Fe3+Shows complete fluorescence quenching effect and is expected to become Fe3+The fluorescent probe of (1).
As can be seen from FIG. 5(a), the fluorescence intensity of the cadmium complex prepared in example 1 showed a dependency on the type of anion in the selected aqueous anion solution, with only Cr2O7 2-Shows complete fluorescence quenching effect and is expected to become Cr2O7 2-The fluorescent probe of (1).
As can be seen from fig. 6(a), in the selected aqueous antibiotic solution, the fluorescence intensity of the cadmium complex prepared in example 1 shows dependence on the type of antibiotic, and nitrofurazone and nitrofurantoin show complete fluorescence quenching effect, and thus, the cadmium complex is expected to be a fluorescent probe for nitrofurazone and nitrofurantoin.
To investigate Fe in the cadmium Complex recognition aqueous solution prepared in example 13+、Cr2O7 2-Sensitivity of NZF and NFT, Fe3+、Cr2O7 2-NZF and NFT are added into the aqueous suspension of the material to prepare suspensions with different concentrations, and the change of the fluorescence intensity of the suspensions is recorded. As shown in FIGS. 4, 5 and 6, the fluorescence intensity is dependent on Fe3+、Cr2O7 2-The concentration increases of NZF and NFT still show a downward trend. When Fe3+、Cr2O7 2-The concentrations of NZF and NFT were 3.32X 10, respectively-5mmol·L-1、3.32×10- 5mmol·L-1、1.64×10-3mol·L-1、1.64×10-3mol·L-1When the fluorescence of the complex is basically and completely quenched, the complex is detected in aqueous solutionFe3+、Cr2O7 2-NZF and NFT have high sensitivity.
Example 4 photodegradation of the complex:
30mg of the cadmium complex synthesized by the present invention was weighed into 50mL of methylene blue aqueous solution (10mg/L), rhodamine B aqueous solution (10mg/L), methyl orange aqueous solution (10mg/L) dye, and then 5uL of H was added2O2Stirring in the dark for 30min to make the surface of the complex reach adsorption-desorption equilibrium, then irradiating with visible light while stirring, taking 1mL of methylene blue, methyl orange and rhodamine B aqueous solution every 5min, and immediately testing the change of absorbance (as shown in FIGS. 7, 8 and 9). The photodegradation result shows that the degradation rates of the complex to methylene blue, methyl orange and rhodamine B within 60 minutes are respectively as high as 95.2%, 87.6% and 97.9%, and the complex can be recycled for multiple times (as shown in figure 10).
Claims (3)
1. The cadmium complex used as a ferric ion, dichromate ion, antibiotic nitrofural and nitrofurantoin fluorescent probe and capable of effectively degrading methylene blue, rhodamine B and methyl orange dye is characterized by having a chemical formula of [ Cd (L) (H)2O)·5H2O]nWherein H is2L ═ 1, 1 '- (4-carboxyphenyl) -2, 2' -biimidazole; the crystal of the cadmium complex belongs to a monoclinic system, and the space group is P21And c, unit cell parameters are as follows:
α gamma 90 deg. and β gamma 114.354(5 deg.), the central ion cadmium is hexa-coordinated octahedral configuration, and the cadmium ion is coordinated with 1, 1 '- (4-carboxyl phenyl) -2, 2' -biimidazole carboxyl oxygen atom and imidazole nitrogen atom to form complex three-dimensional cadmium coordination polymer.
2. A method of producing cadmium metal as claimed in claim 1, comprising the steps of: under the sealing condition, organic ligand 1, 1 '- (4-carboxyphenyl) -2, 2' -biimidazole and cadmium nitrate tetrahydrate are subjected to hydrothermal reaction in an aqueous solution to obtain the cadmium complex with a crystal structure.
3. The method of claim 2, wherein: the molar ratio of 1, 1 '- (4-carboxyphenyl) -2, 2' -biimidazole to cadmium nitrate tetrahydrate is 1: 1, 10mL of deionized water is used for every 0.05mmol of cadmium nitrate tetrahydrate, and the thermal reaction is carried out at 120 ℃ for three days.
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