CN108484927A - A kind of p-nitrophenyl has the zinc-base metal organic frame and preparation method thereof of selective fluorescence identifying - Google Patents
A kind of p-nitrophenyl has the zinc-base metal organic frame and preparation method thereof of selective fluorescence identifying Download PDFInfo
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- CN108484927A CN108484927A CN201810490136.3A CN201810490136A CN108484927A CN 108484927 A CN108484927 A CN 108484927A CN 201810490136 A CN201810490136 A CN 201810490136A CN 108484927 A CN108484927 A CN 108484927A
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- zinc
- base metal
- metal organic
- organic frame
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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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- 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
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- 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
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
-
- 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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- 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
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N2021/6432—Quenching
Abstract
The present invention relates to the zinc-base metal organic frame that a kind of p-nitrophenyl has selective fluorescence identifying, chemical formula C78H62Zn3N12O21；The present invention also provides preparation methods, include the following steps：By zinc nitrate hexahydrate, 1,3 bis- (1 base of imidazoles) benzene, 4,4 ' oxydibenzoic acids, N, N dimethylformamides, second alcohol and water are added into reaction kettle；Said mixture is warming up to 110 130 DEG C, after reacting 65 80 hours, 18 25 DEG C is cooled to, obtains colourless bulk crystals；Crystal is collected, and is washed successively using water and ethyl alcohol, zinc-base metal organic frame can be obtained after vacuum drying.Collaboration coordination of the preparation method based on the stronger coordination ability of divalent zinc ion and two kinds of organic ligands, is made zinc-base metal organic frame, new direction is indicated to prepare Multifunction fluorescent metal-organic framework material；The zinc-base metal organic frame can be used as the fluorescence identifying material to small organic molecule, be had potential application in materialogy field.
Description
Technical field
The present invention relates to zinc-base metal organic frame and its preparation sides that a kind of p-nitrophenyl has selective fluorescence identifying
Method belongs to fluorescence identifying field of material preparation.
Background technology
Fluorescence identifying as a kind of using Fluorescence solid-state material as the novel detection identification technology of matrix, compared to traditional spy
Survey identification technology has many advantages, such as efficient, highly sensitive, time-consuming few.Fluorescence identifying will likely substitute conventional method such as Raman spectrum
Gentle ion mobility spectrometry (IMS) becomes the efficient and sensible of great exploitation potential and takes short fluorescence identification technique.As fluorescence
The characteristic of the core of identification technology, Fluorescence solid-state material directly influences the performances such as the sensitive and efficiency of fluorescence identifying, because
The research of this Fluorescence solid-state material is particularly important.
In recent years, due to its Scalability and Modulatory character, small organic molecule fluorescence identifying material is by chemical research
The extensive concern of person.Referring to：W.P.Lustig,S.Mukherjee,N.-D.Rudd,A.V.Desai,J.Li,S.K.Ghosh,
Chem.Soc.Rev.,2017,46,3242；Z.-Q.Liu,Y.-Q.Zhou,W.-Y.Sun,Chinese J.Inorg.Chem.,
2017,33,1959。
It is heavy metal polymerization of olefin using catalyst polymer that the fluorescence identifying material reported, which has most, referring to：D.Tian,Y.Li,
R.-Y.Chen,Z.Chang,G.-Y.Wang,X.-H.Bu,J.Mater.Chem.A,2014,2,1465；Y.Li,S.-
S.Zhang,D.-T.Song,Angew.Chem.,2013,125,738；Z.Sun,M.Yang,Y.Ma,L.-C.Li,
Cryst.Crowth Des.,2017,17,4326.Due to knowing to the selective fluorescence of small organic molecule (such as nitrobenzene)
Other zinc-base metal organic frame acquires a certain degree of difficulty in synthesis, therefore the fluorescence identifying material based on zinc-base metal organic frame
Research it is less, referring to：X.-J.Liu,X.Wang,J.-L.Xu,D.Tian,R.-Y.Chen,J.Xu,X.-H.Bu,Dalton
Trans.,2017,46,4893；R.-X.Yao,X.Cui,X.-X.Jia,F.-Q.Zhang,X.-M.Zhang,
Inorg.Chem.,2016,55,9270。
It is therefore desirable to invent a kind of new p-nitrophenyl have selective fluorescence identifying zinc-base metal organic frame and
Preparation method, to overcome the above problem.
Invention content
It is an object of the invention to overcome the defect of the prior art, a kind of zinc-base gold of p-nitrophenyl fluorescence identifying is provided
Belong to organic frame and preparation method thereof, the preparation method is based on the stronger coordination ability of divalent zinc ion and two kinds of organic ligands
Collaboration coordination, is made zinc-base metal organic frame, and the metal to prepare the selective fluorescence identifying of p-nitrophenyl has machine frame
Frame indicates new direction；The zinc-base metal organic frame p-nitrophenyl has highly sensitive and Selective recognition, in fluorescence identifying
There is potential using value in terms of nuisance.
The invention is realized in this way：
The present invention provides a kind of zinc-base metal organic frame of the p-nitrophenyl with fluorescence identifying, and the p-nitrophenyl has
The chemical formula of the zinc-base metal organic frame of selective fluorescence identifying is C78H62Zn3N12O21。
Further, there is the p-nitrophenyl crystal of the zinc-base metal organic frame of selective fluorescence identifying to belong to just
Friendship crystallographic system, Ibca space groups, cell parameter are：α=90 °, β=
90 °, γ=90 °.
The present invention also provides the preparation sides that a kind of p-nitrophenyl has the zinc-base metal organic frame of selective fluorescence identifying
Method includes the following steps：Step 1：By bis- (imidazoles -1- bases) benzene of zinc nitrate hexahydrate, 1,3-, 4,4 '-oxydibenzoic acids,
N,N-Dimethylformamide, second alcohol and water are added into reaction kettle, and are uniformly mixed；Step 2：Said mixture is warming up to
110-130 DEG C, after reacting 65-80 hours, it is cooled to 18-25 DEG C, obtains colourless bulk crystals；Step 3：It collects above-mentioned colourless
Bulk crystals, and washed successively using water and ethyl alcohol, after vacuum drying, you can obtaining p-nitrophenyl has selective fluorescence
The zinc-base metal organic frame of identification.
Further, bis- (imidazoles -1- bases) benzene of zinc nitrate hexahydrate, 1,3-, 4,4 '-oxydibenzoic acids, N, N- diformazans
Usage ratio respectively (0.1-0.3 mMs), (0.1-0.3 mMs), (the 0.1-0.3 mmoles of base formamide, second alcohol and water
You), (4-6 milliliters), (1-3 milliliters), (2.5-4 milliliters).
Further, bis- (1H- imidazoles -1- bases) benzene of zinc nitrate hexahydrate, 1,3-, 4,4 '-oxydibenzoic acids, N, N- bis-
Methylformamide, the usage ratio of second alcohol and water be respectively 0.2 mM, 0.2 mM, 0.2 mM, 5 milliliters, 2 milliliters,
3 milliliters.
The invention has the advantages that：
Collaboration of the preparation method provided by the invention based on divalent zinc ion stronger coordination ability and two kinds of organic ligands
Coordination, is made zinc-base metal organic frame, and the metal organic frame to prepare the selective fluorescence identifying of p-nitrophenyl refers to
Bright new direction；The zinc-base metal organic frame p-nitrophenyl has highly sensitive and Selective recognition, harmful in fluorescence identifying
Object space face has potential using value.
Description of the drawings
In order to more clearly explain the embodiment of the invention or the technical proposal in the existing technology, to embodiment or will show below
There is attached drawing needed in technology description to be briefly described, it should be apparent that, the accompanying drawings in the following description is only this
Some embodiments of invention for those of ordinary skill in the art without creative efforts, can be with
Other attached drawings are obtained according to these attached drawings.
Fig. 1 is the zinc-base metal organic frame that p-nitrophenyl provided in an embodiment of the present invention has selective fluorescence identifying
Crystal structure figure；
Fig. 2 is p-nitrophenyl provided in an embodiment of the present invention, and there is the zinc-base metal organic frame of selective fluorescence identifying to exist
The fluorescence intensity maximum value column diagram tested under different solvents；
Fig. 3 is the zinc-base metal organic frame that p-nitrophenyl provided in an embodiment of the present invention has selective fluorescence identifying
Nitrobenzene titration fluorescence collection of illustrative plates.
Specific implementation mode
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 describes, 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, those of ordinary skill in the art obtained without making creative work it is all its
Its embodiment, shall fall within the protection scope of the present invention.
Such as Fig. 1 to Fig. 3, the embodiment of the present invention provides a kind of p-nitrophenyl, and there is the zinc-base metal of selective fluorescence identifying to have
There is the chemical formula of the zinc-base metal organic frame of selective fluorescence identifying to be for machine frame, the p-nitrophenyl
C78H62Zn3N12O21.There is the p-nitrophenyl crystal of the zinc-base metal organic frame of selective fluorescence identifying to belong to orthorhombic
System, Ibca space groups, cell parameter are：α=90 °, β=90 °, γ
=90 °.
The present invention also provides the preparation sides that a kind of p-nitrophenyl has the zinc-base metal organic frame of selective fluorescence identifying
Method includes the following steps：
Step 1：By bis- (imidazoles -1- bases) benzene of zinc nitrate hexahydrate, 1,3-, 4,4 '-oxydibenzoic acids, N, N- diformazans
Base formamide, second alcohol and water are added into reaction kettle, and are uniformly mixed, wherein the bis- (imidazoles -1- of zinc nitrate hexahydrate, 1,3-
Base) benzene, 4,4 '-oxydibenzoic acids, N,N-dimethylformamide, second alcohol and water usage ratio be respectively (0.1-0.3 mmoles
You), (0.1-0.3 mMs), (0.1-0.3 mMs), (4-6 milliliters), (1-3 milliliters), (2.5-4 milliliters).It is preferable at this
In embodiment, bis- (imidazoles -1- bases) benzene of zinc nitrate hexahydrate, 1,3-, 4,4 '-oxydibenzoic acids, n,N-Dimethylformamide,
The usage ratio of second alcohol and water is respectively 0.2 mM, 0.2 mM, 0.2 mM, 5 milliliters, 2 milliliters, 3 milliliters.In addition,
The reaction kettle contains 20-25 milliliters of polytetrafluoroethyllining linings.
Step 2：Said mixture is warming up to 110-130 DEG C, after reacting 65-80 hours, 18-25 DEG C is cooled to, obtains
Bulk crystals.In the preferred embodiment, specific operate is：Said mixture is warming up to 120 DEG C, after reacting 72 hours,
20 DEG C are cooled to, colourless bulk crystals are obtained.
Step 3：Above-mentioned bulk crystals are collected, and are washed successively using water and ethyl alcohol, after vacuum drying, you can
To target product：P-nitrophenyl has the zinc-base metal organic frame of selective fluorescence identifying.
Obtained target product is characterized：
1. carrying out fluorescence data test to the metal organic frame obtained using F-4600 types Fluorescence Spectrometer, Fig. 2 is
The fluorescence intensity maximum value cylindricality tested under different solvents using the zinc-base metal organic frame of Origin Software on Drawing
Scheme, shows that the zinc-base metal organic frame p-nitrophenyl has the complete quenching effect of fluorescence in figure；Fig. 3 is also to use Origin
The nitrobenzene titration fluorescence collection of illustrative plates of the zinc-base metal organic frame of Software on Drawing, and nitrobenzene can be obtained by 3 σ of formula/k
A concentration of 8.7ppm of fluorescence identifying limit.
2. it is (0.23 × 0.19 × 0.17) mm to select size3Crystal be used for ray crystallographic analysis, single crystal diffraction data exist
It is collected on diffractometer, with the Mo-k alpha rays of graphite monochromator monochromatization2.9 °≤θ≤22.8 °, it was demonstrated that this is matched
Position polymer belongs to rhombic system, space group Ibca, and cell parameter is：
α=90 °, β=90 °, γ=90 °.Fig. 1 is the crystal structure figure for the zinc-base metal organic frame for making Diamond Software on Drawing.
In conclusion preparation method provided by the invention is based on the stronger coordination ability of divalent zinc ion and two kinds organic are matched
The collaboration of body is coordinated, and zinc-base metal organic frame is made, and the metal to prepare the selective fluorescence identifying of p-nitrophenyl has
Machine frame indicates new direction；The zinc-base metal organic frame p-nitrophenyl has highly sensitive and Selective recognition, in fluorescence
There is potential using value in terms of identifying nuisance.
The foregoing is merely illustrative of the preferred embodiments of the present invention, is not intended to limit the invention, all essences in the present invention
With within principle, any modification, equivalent replacement, improvement and so on should all be included in the protection scope of the present invention god.
Claims (5)
1. a kind of p-nitrophenyl has the zinc-base metal organic frame of selective fluorescence identifying, which is characterized in that described to nitro
It is C that benzene, which has the chemical formula of the zinc-base metal organic frame of selective fluorescence identifying,78H62Zn3N12O21。
2. there is p-nitrophenyl as described in claim 1 the zinc-base metal organic frame of selective fluorescence identifying, feature to exist
In：There is the p-nitrophenyl crystal of the zinc-base metal organic frame of selective fluorescence identifying to belong to rhombic system, and Ibca is empty
Between group, cell parameter is：α=90 °, β=90 °, γ=90 °.
3. a kind of p-nitrophenyl as claimed in claim 1 or 2 has the zinc-base metal organic frame of selective fluorescence identifying
Preparation method, which is characterized in that include the following steps：
Step 1：By bis- (imidazoles -1- bases) benzene of zinc nitrate hexahydrate, 1,3-, 4,4 '-oxydibenzoic acids, N, N- dimethyl methyls
Amide, second alcohol and water are added into reaction kettle, and are uniformly mixed；
Step 2：Said mixture is warming up to 110-130 DEG C, after reacting 65-80 hours, 18-25 DEG C is cooled to, obtains colourless
Bulk crystals；
Step 3：Above-mentioned bulk crystals are collected, and are washed successively using water and ethyl alcohol, after vacuum drying, you can are obtained pair
Nitrobenzene has the zinc-base metal organic frame of selective fluorescence identifying.
4. p-nitrophenyl as claimed in claim 3 has the preparation side of the zinc-base metal organic frame of selective fluorescence identifying
Method, it is characterised in that：Bis- (imidazoles -1- bases) benzene of zinc nitrate hexahydrate, 1,3-, 4,4 '-oxydibenzoic acids, N, N- dimethyl methyls
Amide, second alcohol and water usage ratio be respectively (0.1-0.3 mMs), (0.1-0.3 mMs), (0.1-0.3 mMs),
(4-6 milliliters), (1-3 milliliters), (2.5-4 milliliters).
5. p-nitrophenyl as claimed in claim 4 has the preparation side of the zinc-base metal organic frame of selective fluorescence identifying
Method, it is characterised in that：Bis- (imidazoles -1- bases) benzene of zinc nitrate hexahydrate, 1,3-, 4,4 '-oxydibenzoic acids, N, N- dimethyl methyls
Amide, second alcohol and water usage ratio be respectively 0.2 mM, 0.2 mM, 0.2 mM, 5 milliliters, 2 milliliters, 3 milliliters.
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Cited By (4)
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| CN109265701A (en) * | 2018-10-22 | 2019-01-25 | 江西理工大学 | A kind of pair of acetylacetone,2,4-pentanedione has the zinc-base metal organic frame and preparation method thereof of selective fluorescence identifying |
| CN111215032A (en) * | 2018-11-26 | 2020-06-02 | 国家纳米科学中心 | Rapid preparation method of MOF material |
| CN114031632A (en) * | 2021-12-18 | 2022-02-11 | 商丘师范学院 | Double-tooth nitrogen ligand zinc complex with stacked structure and preparation method and application thereof |
| CN116396493A (en) * | 2023-04-13 | 2023-07-07 | 天津师范大学 | Cationic metal-organic framework material, and preparation method and application thereof |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109265701A (en) * | 2018-10-22 | 2019-01-25 | 江西理工大学 | A kind of pair of acetylacetone,2,4-pentanedione has the zinc-base metal organic frame and preparation method thereof of selective fluorescence identifying |
| CN109265701B (en) * | 2018-10-22 | 2021-03-16 | 江西理工大学 | Zinc-based metal organic framework with selective fluorescence recognition on acetylacetone and preparation method thereof |
| CN111215032A (en) * | 2018-11-26 | 2020-06-02 | 国家纳米科学中心 | Rapid preparation method of MOF material |
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| CN114031632A (en) * | 2021-12-18 | 2022-02-11 | 商丘师范学院 | Double-tooth nitrogen ligand zinc complex with stacked structure and preparation method and application thereof |
| CN114031632B (en) * | 2021-12-18 | 2023-08-18 | 商丘师范学院 | Double-tooth nitrogen ligand zinc complex with stacked structure and preparation method and application thereof |
| CN116396493A (en) * | 2023-04-13 | 2023-07-07 | 天津师范大学 | Cationic metal-organic framework material, and preparation method and application thereof |
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