CN107793440B - Fluorescence porous material, synthetic method and its application - Google Patents
Fluorescence porous material, synthetic method and its application Download PDFInfo
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- CN107793440B CN107793440B CN201711182923.3A CN201711182923A CN107793440B CN 107793440 B CN107793440 B CN 107793440B CN 201711182923 A CN201711182923 A CN 201711182923A CN 107793440 B CN107793440 B CN 107793440B
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- 239000011148 porous material Substances 0.000 title claims abstract description 60
- 238000010189 synthetic method Methods 0.000 title claims abstract description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 41
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 21
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 claims abstract description 21
- 239000000463 material Substances 0.000 claims abstract description 15
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 13
- 239000003446 ligand Substances 0.000 claims abstract description 9
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims abstract description 8
- 239000000126 substance Substances 0.000 claims abstract description 4
- 239000013078 crystal Substances 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 7
- 238000001917 fluorescence detection Methods 0.000 claims description 6
- 239000000725 suspension Substances 0.000 claims description 6
- 230000004044 response Effects 0.000 claims description 5
- 235000019441 ethanol Nutrition 0.000 claims description 4
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 3
- 238000007789 sealing Methods 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000006228 supernatant Substances 0.000 claims 1
- 238000005303 weighing Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 7
- 230000035945 sensitivity Effects 0.000 abstract description 4
- 239000000575 pesticide Substances 0.000 abstract description 3
- 238000012360 testing method Methods 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 2
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000001514 detection method Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 230000002363 herbicidal effect Effects 0.000 description 5
- 239000004009 herbicide Substances 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- -1 bipyridine cation salt Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 1
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 1
- 241001464837 Viridiplantae Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000012271 agricultural production Methods 0.000 description 1
- WLZRMCYVCSSEQC-UHFFFAOYSA-N cadmium(2+) Chemical compound [Cd+2] WLZRMCYVCSSEQC-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 238000002447 crystallographic data Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000000954 titration curve Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
Classifications
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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
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6402—Atomic fluorescence; Laser induced fluorescence
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
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- Biochemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Analytical Chemistry (AREA)
- Optics & Photonics (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Engineering & Computer Science (AREA)
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- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
The present invention relates to fluorescence porous materials preparation technical fields, in particular to a kind of fluorescence porous material, synthetic method and its application.A kind of fluorescence porous material in the present invention, chemical formula C26H16N7O9Cd2, main ligand are 1,3,5- tri- imidazole radicals benzene, and assistant ligand is butene dioic acid, and solvent is n,N-Dimethylformamide；It is prepared by solvent heating, heretofore described fluorescence porous material raw material is simple, and preparation process is simple, and has higher thermal stability and fluorescent emission performance.During this material tests pesticide paraquat, high sensitivity is shown, and detecting and selecting property is good, had a good application prospect in materials science field.
Description
Technical field
The present invention relates to fluorescence porous materials preparation technical field, in particular to a kind of fluorescence porous material,
Synthetic method and its application.
Background technique
Research of the fluorescence porous material in many optical device fields is increasingly deep, the fluorescence probe material as a kind of new property
Material, usually shows that high sensitivity, selectivity good, response time be short and simple operation and other advantages, and part fluorescence probe
Material has Ke Xunhuanliyong property, can be realized the fluorescence detection in different solvents, effectively facilitates the quotient of fluorescence porous material
Industry application, therefore constructing highly sensitive, high stability the porous probe material of fluorescence is a significant research.
Currently, in agricultural production, the health for seriously endangering us is excessively used in pesticide, according to literature survey hundred
Careless withered (1-1- dimethyl -4-4 bipyridine cation salt) is a kind of quick steriland herbicide, can be absorbed by green plants rapidly
Keep its withered, therefore farmer can spray herbicide for quick herbicidal in plant growing process, although, herbicide pair
There is elimination effect in crops, then the pharmacological property in herbicide can be absorbed by crops, therefore, in crops can be contained a certain amount of
Toxicity, long-term consumption can do great harm to human body, but due in crops content it is lower, and there is no a kind of on the market
Detection material can fast and accurately detect the content of paraquat.
Summary of the invention
In view of the above-mentioned problems, the purpose of the present invention is to provide a kind of fluorescence porous material, synthetic method and its application,
The detection material is high to the detection sensitivity of paraquat, and the response time is short.,
To achieve the above object, the invention adopts the following technical scheme:
A kind of fluorescence porous material, chemical formula C26H16N7O9Cd2, main ligand is 1,3,5- tri- imidazole radicals benzene, auxiliary
Helping ligand is butene dioic acid, and solvent is n,N-Dimethylformamide；
Preparation method is as follows:
Step 1 weighs tri- imidazole radicals benzene of 1,3,5-, butene dioic acid, four nitric hydrate cadmiums according to molar ratio 3:5:1
Mixing, obtains mixture A；
Mixture A is put into the container of the solvent equipped with n,N-Dimethylformamide by step 2, the mixture A with
The amount ratio of n,N-Dimethylformamide is 0.05 mM: 6.00 milliliter, is ultrasonically treated 10 minutes, stirs evenly, mixed
Close liquid B；
It is in ptfe autoclave, 95 after sealing that mixed liquid B obtained in step 2 is put into material by step 3
Incubating solvent thermal response is carried out at DEG C, the reaction time is 72 hours, and faint yellow bulk crystals are obtained after cooled to room temperature；
Faint yellow bulk crystals obtained in step 3 are used point of N,N-dimethylformamide and ethyl alcohol by step 4 respectively
It is not washed, can be prepared by fluorescence porous material of the present invention after dry.
Preferably, the material of reaction kettle described in step 2 is polytetrafluoroethylene (PTFE).
The fluorescence porous material is for detecting detection low concentration paraquat.
The application of the fluorescence porous material is as follows:
The fluorescence porous material is configured to suspension, paraquat solution is then instilled into porous material suspension
In, then detected by the fluorescence of porous material.
The fluorescence porous material is limited to 0.217mmol/L to the theoretical fluorescence detection of paraquat.
The invention has the following advantages: fluorescence porous material raw material described in the invention is simple, preparation process is simple,
And there are higher thermal stability and fluorescent emission performance.During this material tests pesticide paraquat, sensitivity is shown
Height, and detecting and selecting property is good, has a good application prospect in materials science field.
Detailed description of the invention
Fig. 1 is the frame construction drawing of fluorescence porous material in the present invention；
Fig. 2 is the tomograph of fluorescence porous material in the present invention；
Fig. 3 is the two-dimensional layered structure figure of fluorescence porous material in the present invention；
Fig. 4 is the hot weight curve of fluorescence porous material in the present invention；
Fig. 5 is the fluorescence emission spectrogram of compound of fluorescence porous material in the present invention；
Fig. 6 be in the present invention fluorescence porous material to the fluorescence detection spectroscopic data coordinate diagram of paraquat.
Specific embodiment
Following will be combined with the drawings in the embodiments of the present invention, and technical solution in the embodiment of the present invention carries out clear, complete
Site preparation description, it is clear that described embodiments are only a part of the embodiments of the present invention, instead of all the embodiments.It is based on
Embodiment in the present invention, it is obtained by those of ordinary skill in the art without making creative efforts every other
Embodiment shall fall within the protection scope of the present invention.
Embodiment one
A kind of fluorescence porous material, chemical formula C26H16N7O9Cd2, main ligand is 1,3,5- tri- imidazole radicals benzene, auxiliary
Helping ligand is butene dioic acid, and solvent is n,N-Dimethylformamide；
Preparation method is as follows:
Step 1 weighs tri- imidazole radicals benzene of 1,3,5-, butene dioic acid, four nitric hydrate cadmiums according to molar ratio 3:5:1
Mixing, obtains mixture A；
Mixture A is put into the container of the solvent equipped with n,N-Dimethylformamide by step 2, the mixture A with
The amount ratio of n,N-Dimethylformamide is 0.05 mM: 6.00 milliliter, is ultrasonically treated 10 minutes, stirs evenly, mixed
Close liquid B；
Mixed liquid B obtained in step 2 is put into reaction kettle by step 3, carries out incubating solvent after sealing at 95 DEG C
Thermal response, reaction time are 72 hours, and faint yellow bulk crystals are obtained after cooled to room temperature；
As shown in Figure 1, mixed liquid B is in heated at constant temperature in this step, a dinuclear metal cluster and two lists in frame
Core cadmium ion and butene dioic acid are coordinated, and are alternately arranged, and a kind of wavy one-dimensional chain structure, one-dimensional chain parallel to each other are formed
By the connection of Carboxylic acid ligand, expanding becomes two-dimensional layered structure；
As shown in Fig. 2, three adjacent two-dimensional layers are sequentially connected by three imidazole groups, and then three-dimensional MOF has been expanded into it
Structure, as shown in Figure 3.
As shown in Fig. 4, it is about with the porosity of the PLATON method calculating fluorescence porous material structure
34.5%, porous material thermal stability loses solvent molecule before 200 DEG C, and frame gradually collapses since 300 DEG C, works as temperature
500 DEG C of porous materials are reached to decompose completely.Fluorescence porous material of the present invention is crystallized in anorthic system, P -1 space group,
Cell parameter is respectively as follows:
Faint yellow bulk crystals obtained in step 3 are used point of N,N-dimethylformamide and ethyl alcohol by step 4 respectively
It is not washed, can be prepared by fluorescence porous material of the present invention after dry.
Embodiment two
Fluorescence porous material obtained in embodiment one is used to detect detection low concentration paraquat in the present embodiment.
Detection method is as follows: the fluorescence porous material being configured to suspension, then instills paraquat solution
In porous material suspension, then detected by the fluorescence of porous material.
The fluorescence porous material is limited to 0.217mmol/L to the theoretical fluorescence detection of paraquat.
Experiment one
To in embodiment one to obtained fluorescence porous material crystal structure be measured
The monocrystalline for choosing suitable size under the microscope, measures on single crystal diffractometer, temperature 293K.All diffraction numbers
According to using SADABS program to carry out absorption correction, cell parameter is determined with least square method.Data convert and structure elucidation difference
It is completed using SAINT and SHELXTL program.First whole non-hydrogen atom coordinates are determined with difference function method and least square method, and
The hydrogen atom position of main body framework is obtained with theoretical hydrogenation method, refine then is carried out to crystal structure with least square method.Crystal
The partial parameters for learning point diffraction data collection and structure refinement see the table below 1.
Table 1: the crystal parameter table of the porous material
R1 a=Σ | | Fo|-|Fc||/Σ|Fo|；wR2 b=[Σ [w (Fo 2-Fc 2)2]/Σw(Fo 2)2]1/2.
Experiment two
To in embodiment one to obtained fluorescence porous material luminescent properties measurement
Porous material crystal is fully ground, 3mg powder is successively taken to be put into five vials.It is separately added into 3mL's
Organic reagent, subsequent ultrasound 10min, makes powder sample be uniformly dispersed.Attached drawing 5 is the fluorescence emission spectrum of porous material, fluorescence
The result shows that suspension shows stronger fluorescence emission peak at 325nm respectively under the excitation wavelength of 275nm.And it is porous
Material all has fluorescent emission behavior in different organic solvents, and it is molten to respectively include methanol, ethyl alcohol, acetonitrile, DMAC and DMF
Agent, it was demonstrated that porous material possesses stable fluorescent emission performance in different organic solvents.To the fluorescence titration curve of paraquat
The results show that the fluorescence intensity of solution constantly reduces with the increase of paraquat additional amount.It is when 5 μ L concentration are only added
When the paraquat solution of 0.1mol/L, the fluorescence intensity quenching rate of solution is 13.5%, and when 13 μ L is added, the fluorescence of solution is strong
Degree quenching rate reaches 93.1%, and porous material is very sensitive to the detection of paraquat.The Fitting Calculation porous material is to paraquat
Detection limit is about 0.217mmol/L, the fluorescence detection paraquat test experiments of the porous material, acquired results such as 6 institute of attached drawing
Show, uses Origin Software on Drawing.Above the experimental results showed that the porous material is one can fast implement and contain to paraquat
Measure the fluorescent material of detection.
In addition, it should be understood that although this specification is described in terms of embodiments, but not each embodiment is only wrapped
Containing an independent technical solution, this description of the specification is merely for the sake of clarity, and those skilled in the art should
It considers the specification as a whole, the technical solutions in the various embodiments may also be suitably combined, forms those skilled in the art
The other embodiments being understood that.
Claims (5)
1. a kind of fluorescence porous material, chemical formula C26H16N7O9Cd2, main ligand are 1,3,5- tri- imidazole radicals benzene, auxiliary
Ligand is butene dioic acid, and solvent is n,N-Dimethylformamide；The molecular weight of the compound is 795.28g ﹒ mol-1, space group is
P-1, anorthic system, unit cell length on space a, b, c-axis direction are respectively Unit-cell volume is
2. a kind of synthetic method of fluorescence porous material described in claim 1, it is characterised in that: the synthetic method is such as
Under:
Tri- imidazole radicals benzene of 1,3,5-, butene dioic acid, four nitric hydrate cadmiums are carried out weighing according to molar ratio 3:5:1 and mixed by step 1
It closes, obtains mixture A；
Mixture A is put into the container of the solvent equipped with n,N-Dimethylformamide by step 2, described mixture A and N, N-
The amount ratio of dimethylformamide is 0.05 mM: 6.00 milliliter, is ultrasonically treated 10 minutes, stirs evenly, obtain mixed liquor
B；
It is in ptfe autoclave, after sealing at 95 DEG C that mixed liquid B obtained in step 2 is put into material by step 3
Incubating solvent thermal response is carried out, the reaction time is 72 hours, and faint yellow bulk crystals are obtained after cooled to room temperature；
Faint yellow bulk crystals obtained in step 3 wash with N,N-dimethylformamide and ethyl alcohol by step 4 respectively
It washs, can be prepared by the fluorescence porous material after dry.
3. a kind of application of fluorescence porous material as described in claim 1, it is characterised in that: the porous material of the fluorescence
Material is for detecting low concentration paraquat.
4. the application of fluorescence porous material according to claim 3, it is characterised in that: the fluorescence porous material
Application it is as follows: the fluorescence porous material is configured to suspension, then by paraquat solution instill porous material hang
In supernatant liquid, then detected by the fluorescence of porous material.
5. the application of fluorescence porous material according to claim 3, it is characterised in that: the fluorescence porous material
0.217mmol/L is limited to the theoretical fluorescence detection of paraquat.
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