CN106966963B - A kind of fluorescence probe and its preparation method and application - Google Patents
A kind of fluorescence probe and its preparation method and application Download PDFInfo
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- CN106966963B CN106966963B CN201710172689.XA CN201710172689A CN106966963B CN 106966963 B CN106966963 B CN 106966963B CN 201710172689 A CN201710172689 A CN 201710172689A CN 106966963 B CN106966963 B CN 106966963B
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- 239000000523 sample Substances 0.000 title claims abstract description 60
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims abstract description 30
- 235000011180 diphosphates Nutrition 0.000 claims abstract description 18
- 239000000376 reactant Substances 0.000 claims abstract description 14
- 239000007787 solid Substances 0.000 claims abstract description 12
- 239000007864 aqueous solution Substances 0.000 claims abstract description 10
- 238000001914 filtration Methods 0.000 claims abstract description 10
- AJKVQEKCUACUMD-UHFFFAOYSA-N 2-Acetylpyridine Chemical compound CC(=O)C1=CC=CC=N1 AJKVQEKCUACUMD-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 8
- 239000002994 raw material Substances 0.000 claims abstract description 8
- ZRYZBQLXDKPBDU-UHFFFAOYSA-N 4-bromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C=C1 ZRYZBQLXDKPBDU-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000005977 Ethylene Substances 0.000 claims abstract description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 7
- 230000007935 neutral effect Effects 0.000 claims abstract description 7
- 230000001376 precipitating effect Effects 0.000 claims abstract description 6
- 239000000243 solution Substances 0.000 claims abstract description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 39
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- 239000003153 chemical reaction reagent Substances 0.000 claims description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 230000005284 excitation Effects 0.000 claims description 8
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical class C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 7
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 7
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical class [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 7
- 239000000908 ammonium hydroxide Chemical class 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 238000012360 testing method Methods 0.000 claims description 6
- 239000012488 sample solution Substances 0.000 claims description 4
- 238000004458 analytical method Methods 0.000 claims description 3
- -1 dimethyl formyl Amine Chemical class 0.000 claims description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims 1
- 238000004445 quantitative analysis Methods 0.000 abstract description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 235000019441 ethanol Nutrition 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 229940048084 pyrophosphate Drugs 0.000 description 12
- 150000001450 anions Chemical class 0.000 description 7
- 238000001514 detection method Methods 0.000 description 5
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000005838 radical anions Chemical class 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000233805 Phoenix Species 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- NOWVLMYARDSBEV-UHFFFAOYSA-N ethene;pyridine Chemical group C=C.C1=CC=NC=C1 NOWVLMYARDSBEV-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000007421 fluorometric assay Methods 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000005272 metallurgy Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229940005657 pyrophosphoric acid Drugs 0.000 description 1
- 238000004451 qualitative analysis Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/22—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/127—Preparation from compounds containing pyridine rings
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- 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"
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- Chemical & Material Sciences (AREA)
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- Immunology (AREA)
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- Life Sciences & Earth Sciences (AREA)
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- Materials Engineering (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
Abstract
The invention discloses a kind of fluorescence probe and its preparation method and application, the fluorescence probe is using ethyl alcohol as solvent, to be reacted using 4- bromobenzaldehyde, 2- acetylpyridine, 4- pyridine ethylene and brominated alkanes as primary raw material, obtain reactant；Reactant taking-up is cooled to room temperature, precipitating is generated, solid is obtained after filtering, solid is then dried into obtain object A；By object A and Zn2+It is mixed in neutral aqueous solution by concentration ratio 1:1, obtains fluorescence probe.The present invention has and can carry out quantitative analysis to pyrophosphate concentration in solution, and quantitative analysis concentration is low, and strong antijamming capability, easy to operate, as a result visually, analyzes easy feature.
Description
Technical field
The present invention relates to a kind of probe and its preparation method and application, especially a kind of fluorescence probe and preparation method thereof and
Using.
Background technique
No Ji O hydrochlorate has a wide range of applications them in the food industry and can be used as food additives, for improveing food
The phoenix taste and quality of product, wherein play a role it is mostly be therein containing sympathizing with acid radical anion.Hydrochlorate is sympathized with also in addition, sympathizing with hydrochlorate and gathering
It is widely used in paint scrubber, water treatment procedure, colored film and rinses and put print, ore dressing and oil industry and fiber and paper maker
In industry simultaneously, they or a kind of excellent anti-pigment of environment-friendly type, are applied in metallurgy and anti-corrosion of metal.It is water such as pyrophosphoric acid
Solution generates one of the product of energy, takes part in the bio-energy process in cell；Under severe conditions, it may also participate in some thin
The generation of tight hormone in bacterium and plant cell, various Han O acid radical anions not only have a wide range of applications in the industry,
Also play a significant role in organism, serious problem of environmental pollution can also be generated by being excessively used, therefore, to containing sympathize with acid group yin from
The identification of son grinds the meaning that makes internal disorder or usurp with important with detection.
Design synthesis can realize the visual method inspection to PPi to the selective fluorescence probe of pyrophosphate (PPi)
It surveys, detection method efficiently accurate in this way is all significant in environment, medicine and field of biology.
Summary of the invention
The object of the present invention is to provide a kind of fluorescence probes and its preparation method and application.The present invention has can be to molten
Pyrophosphate concentration carries out quantitative analysis in liquid, and quantitative analysis concentration is low, and strong antijamming capability, easy to operate, as a result visually,
Analyze easy feature.
Technical solution of the present invention: a kind of fluorescence probe, the molecular formula of the probe are as follows: C40H45N4ZnBr；Structural formula is such as
Shown in attached drawing 1.
A kind of preparation method of fluorescence probe above-mentioned, includes the following steps:
(1) with 4- bromobenzaldehyde, 2- acetylpyridine, 4- pyridine ethylene and brominated alkanes, ammonium hydroxide, acid chloride, triphenyl phasphine, three
Ethamine and dimethylformamide (DMF) raw material stir 1~3 hour at 0~5 DEG C, reflux 18~24, it is stirred at room temperature 30~
60 minutes, filtering must be precipitated, is recrystallized in acetic acid, reactant is obtained；
(2) the reactant taking-up of step (1) is cooled to room temperature, generates precipitating, solid is obtained after filtering, then will
Solid dries to obtain object A；
(3) by object A and Zn2+It is mixed in neutral aqueous solution by concentration ratio 1:1, obtains fluorescence probe.
The preparation method of fluorescence probe above-mentioned is with 4- bromobenzaldehyde, 2- acetylpyridine, 4- pyrrole in the step (1)
Pyridine ethylene and brominated alkanes, ammonium hydroxide, acid chloride, triphenyl phasphine, triethylamine and dimethylformamide (DMF) raw material stir 2 at 3 DEG C
Hour, it flows back 22 hours, is stirred at room temperature 45 minutes, filtering must be precipitated, recrystallized in acetic acid, reactant is obtained.
A kind of application of fluorescence probe above-mentioned in selection identification pyrophosphate.
Application of the fluorescence probe above-mentioned in selection identification pyrophosphate, the knowledge method for distinguishing is to use fluorescence probe
Water dilution, is made fluorescent reagent, sample to be identified is then instilled into the reagent, obtains sample solution, carries out to sample solution
Fluorescence excitation and the glimmering light activated wavelength of fluorescence of test analysis.
Application of the fluorescence probe above-mentioned in selection identification pyrophosphate, the glimmering light activated excitation wavelength are
351nm, when sample to be identified is added and recognizes pyrophosphate, the fluorescence maximum emission wavelength of reagent by 448nm red shift to
550nm。
Fluorescence probe above-mentioned identifies the application in pyrophosphate in selection, the concentration of fluorescence probe in the fluorescent reagent
It is 1.00 × 10-5mol·L-1。
Beneficial effects of the present invention:
1, quantitative analysis of the present invention for pyrophosphate PPi in neutral aqueous solution, the linear concentration of quantitative analysis is most
Low value is 1.0 × 10-7mol·L-1,
2, other that common zwitterion not interference measurement coexists.
3, operation of the present invention is simple, and test result is visual, analyzes more direct.
To further illustrate beneficial effects of the present invention, inventor has done following experiment:
One, qualitative analysis is tested
It 1, is 10 in concentration range-6~10-4In the fluorescence probe aqueous solution of mol/L, when excitation wavelength is 351nm, visit
Needle fluorescence shows as yellow again from 448nm red shift to 530nm；The detection of pyrophosphate (PPi) limits most down to 10-7mol·L-1。
Two, test of quantitative analysis
1, fluorescence probe is diluted to 1.00 × 10 as needed-5mol·L-1。
2, the anion salt for weighing excellent pure grade is configured to the aqueous solution of 100mL, anion concentration 10-2mol/L.According to need
It is diluted step by step with secondary water；The salt for weighing the chloride ion of excellent pure grade is configured to the aqueous solution of 100mL, cation concn 10- 2mol/L.It is diluted step by step with secondary water as needed；
3, it takes respectively in 5 10.0mL volumetric flasks and is separately added into fluorescence probe 1.00 × 10-4mol·L-1Titer
1.0mL is separately added into 1.00 × 10-4mol·L-1, 0,0.2,0.5,1,2 milliliters of PPi mixture solution is diluted to scale and shakes
It is even, it is placed at room temperature for 5 minutes；
4, it introduces fluorescence spectrum to be measured, excitation wavelength 351nm.
5, using PPi concentration as abscissa, fluorescence intensity is ordinate, obtains working curve.
6, sample measures, and takes 10.0mL volumetric flask, and it is 1.00 × 10 that concentration and probe concentration, which is added,-4mol·L-11.0mL is added
PPi solution, is diluted to scale, is placed at room temperature for 5 minutes, and the quartz colorimetric utensil for introducing 3.0cm carries out fluoremetry, strong according to fluorescence
Degree finds sample concentration on working curve.The minimum concentration value of detection identification is 1.0 × 10-7mol·L-1。
Three, other anions and canons fluorescence excite comparative experiments
Preparing anion concentration respectively is 1.00 × 10-2mol·L-1And containing only OH-、ACO-、ClO-、Br-、Cl-、F-、
NO3 -、SO4 2-、BF4 -、H2PO4 -、HSO4 -、I-, PPi, only identify PPi when, fluorescence again from 448nm red shift 530nm, and
And yellow fluorescence is issued under the irradiation of 365nm ultraviolet lamp.
Four, anti-interference test
Other anion OH are added after fluorescence probe identifies PPi-、ACO-、ClO-、Br-、Cl-、F-、NO3 -、SO4 2-、
BF4 -、H2PO4 -、HSO4 -、I-Change in fluorescence it is as shown in Figure 3 and Figure 4, the results showed that fluorescent reagent A detect Zn2+When not by other
Cation influences, the results showed that not by other anion effects when fluorescent reagent detects PPi.
Detailed description of the invention
Fig. 1 is the structural formula of fluorescence probe.
Fig. 2 is fluorescence probe (1.00 × 10-5mol·L-1) and different anions OH-、ACO-、ClO-、Br-、Cl-、F-、
NO3 -、SO4 2-、BF4 -、H2PO4 -、HSO4 -, fluorescence spectrum in the presence of I.
Fig. 3 is influence of the counter anion to reagent Fluorometric assay PPi；
Fig. 4 is fluorescence titration spectrogram of the ppi to fluorescence probe of various concentration；
Fig. 5 is fluorescence probe to identification PPi minimum detection limit；
Fig. 6 is the nuclear magnetic spectrogram of shell A.
Specific embodiment
Below with reference to embodiment, the present invention is further illustrated, but is not intended as the foundation limited the present invention.
The embodiment of the present invention
Embodiment 1: a kind of fluorescence probe, the molecular formula of the fluorescence probe are as follows: C40H45N4ZnBr, structural formula such as attached drawing 1
It is shown.
Embodiment 2: a kind of preparation method of fluorescence probe described in embodiment 1, steps are as follows:
(1) with 4- bromobenzaldehyde, 2- acetylpyridine, 4- pyridine ethylene and brominated alkanes, ammonium hydroxide, acid chloride, triphenyl phasphine, three
Ethamine and dimethylformamide (DMF) raw material stir 2 hours at 3 DEG C, and reflux 22 is stirred at room temperature 45 minutes, must precipitate
Filter, is recrystallized in acetic acid, obtains reactant；
(2) the reactant taking-up of step (1) is cooled to room temperature, generates precipitating, solid is obtained after filtering, then will
Solid dries to obtain object A；The nuclear magnetic spectrum of object A is as shown in Fig. 6；
(3) by object A and Zn2+It is mixed in neutral aqueous solution by concentration ratio 1:1, obtains fluorescence probe.
Embodiment 3: a kind of preparation method of fluorescence probe described in embodiment 1, steps are as follows:
(1) with 4- bromobenzaldehyde, 2- acetylpyridine, 4- pyridine ethylene and brominated alkanes, ammonium hydroxide, acid chloride, triphenyl phasphine, three
Ethamine and dimethylformamide (DMF) raw material stir 3 hours at 0 DEG C, and reflux 18 is stirred at room temperature 30 minutes, must precipitate
Filter, is recrystallized in acetic acid, obtains reactant；
(2) the reactant taking-up of step (1) is cooled to room temperature, generates precipitating, solid is obtained after filtering, then will
Solid dries to obtain object A；
(3) by object A and Zn2+It is mixed in neutral aqueous solution by concentration ratio 1:1, obtains fluorescence probe.
Embodiment 4: a kind of preparation method of fluorescence probe described in embodiment 1, steps are as follows:
(1) with 4- bromobenzaldehyde, 2- acetylpyridine, 4- pyridine ethylene and brominated alkanes, ammonium hydroxide, acid chloride, triphenyl phasphine, three
Ethamine and dimethylformamide (DMF) raw material stir 1 hour at 5 DEG C, and reflux 24 is stirred at room temperature 60 minutes, must precipitate
Filter, is recrystallized in acetic acid, obtains reactant；
(2) the reactant taking-up of step (1) is cooled to room temperature, generates precipitating, solid is obtained after filtering, then will
Solid dries to obtain object A；
(3) by object A and Zn2+It is mixed in neutral aqueous solution by concentration ratio 1:1, obtains fluorescence probe.
Embodiment 5: a kind of application of above-mentioned fluorescence probe in selection identification pyrophosphate, is that fluorescence probe water is dilute
It releases, it is 1.00 × 10 that concentration, which is made,-5mol·L-1Reagent, sample to be identified is then instilled into the reagent, it is molten to obtain sample
Liquid, the laser to sample solution with excitation wavelength for 351nm carry out fluorescence excitation and the glimmering light activated wavelength of fluorescence of test analysis,
When sample to be identified is added and recognizes pyrophosphate, the fluorescence maximum emission wavelength of reagent by 448nm red shift to 550nm,
It proves to recognize pyrophosphate.
Claims (7)
1. a kind of fluorescence probe, it is characterised in that: the molecular formula of the probe are as follows: C40H45N4ZnBr；Structural formula are as follows:
2. a kind of preparation method of fluorescence probe according to claim 1, which comprises the steps of:
(1) with 4- bromobenzaldehyde, 2- acetylpyridine, 4- pyridine ethylene and brominated alkanes, ammonium hydroxide, acid chloride, triphenyl phasphine, triethylamine
It with dimethylformamide (DMF) raw material, stirs 1~3 hour, flows back 18~24 hours at 0~5 DEG C, it is stirred at room temperature 30~
60 minutes, filtering must be precipitated, is recrystallized in acetic acid, reactant is obtained；
(2) the reactant taking-up of step (1) is cooled to room temperature, generates precipitating, solid is obtained after filtering, then by solid
Dry to obtain object A；
(3) by object A and Zn2+It is mixed in neutral aqueous solution by concentration ratio 1:1, obtains fluorescence probe.
3. the preparation method of fluorescence probe according to claim 2, it is characterised in that: be with 4- bromine in the step (1)
Benzaldehyde, 2- acetylpyridine, 4- pyridine ethylene and brominated alkanes, ammonium hydroxide, acid chloride, triphenyl phasphine, triethylamine and dimethyl formyl
Amine (DMF) raw material stirs 2 hours at 3 DEG C, flows back 22 hours, is stirred at room temperature 45 minutes, filtering must be precipitated, in acetic acid
It is recrystallized, obtains reactant.
4. a kind of application of fluorescence probe according to claim 1 in selection identification pyrophosphate.
5. application of the fluorescence probe according to claim 4 in selection identification pyrophosphate, it is characterised in that: the knowledge
Method for distinguishing is that fluorescence probe is diluted with water, and fluorescent reagent is made, sample to be identified is then instilled into the reagent, obtains sample
Product solution carries out fluorescence excitation and the glimmering light activated wavelength of fluorescence of test analysis to sample solution.
6. application of the fluorescence probe according to claim 5 in selection identification pyrophosphate, it is characterised in that: described glimmering
Light activated excitation wavelength is 351nm, when sample to be identified is added and recognizes pyrophosphate, the fluorescence emission maximum of reagent
Wavelength is by 448nm red shift to 550nm.
7. application of the fluorescence probe according to claim 5 in selection identification pyrophosphate, it is characterised in that: described glimmering
The concentration of fluorescence probe is 1.00 × 10 in light reagent-5mol·L-1。
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