CN107840855A - A kind of fluorescence probe and application thereof - Google Patents
A kind of fluorescence probe and application thereof Download PDFInfo
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- CN107840855A CN107840855A CN201711067277.6A CN201711067277A CN107840855A CN 107840855 A CN107840855 A CN 107840855A CN 201711067277 A CN201711067277 A CN 201711067277A CN 107840855 A CN107840855 A CN 107840855A
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- fluorescence probe
- fluorescence
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- 239000000523 sample Substances 0.000 title claims abstract description 51
- 238000001514 detection method Methods 0.000 claims abstract description 16
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims abstract description 8
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229920003026 Acene Polymers 0.000 claims abstract description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052796 boron Inorganic materials 0.000 claims abstract description 4
- 235000019260 propionic acid Nutrition 0.000 claims abstract description 4
- 229940018563 3-aminophenol Drugs 0.000 claims abstract description 3
- 238000006482 condensation reaction Methods 0.000 claims abstract description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 15
- 239000007788 liquid Substances 0.000 claims description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 238000012360 testing method Methods 0.000 claims description 4
- 238000004458 analytical method Methods 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 229960000549 4-dimethylaminophenol Drugs 0.000 claims description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical group C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000004440 column chromatography Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims 2
- 238000010189 synthetic method Methods 0.000 claims 2
- -1 m-aminophenol Compound Chemical class 0.000 claims 1
- 238000003556 assay Methods 0.000 abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 2
- 239000001257 hydrogen Substances 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 abstract 1
- GMKQZLBFXYUXGT-UHFFFAOYSA-N C1C=CC=C1.N1C=CC=CC=C1 Chemical compound C1C=CC=C1.N1C=CC=CC=C1 GMKQZLBFXYUXGT-UHFFFAOYSA-N 0.000 abstract 1
- 229940126214 compound 3 Drugs 0.000 abstract 1
- 239000007850 fluorescent dye Substances 0.000 abstract 1
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 abstract 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000012670 alkaline solution Substances 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 241000933522 Bacillus pseudofirmus OF4 Species 0.000 description 1
- 238000007445 Chromatographic isolation Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000011953 bioanalysis Methods 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- JKRHDMPWBFBQDZ-UHFFFAOYSA-N n'-hexylmethanediimine Chemical compound CCCCCCN=C=N JKRHDMPWBFBQDZ-UHFFFAOYSA-N 0.000 description 1
- QCCWVNLOJADEAV-UHFFFAOYSA-N n,n-dimethyl-1h-pyrrol-3-amine Chemical class CN(C)C=1C=CNC=1 QCCWVNLOJADEAV-UHFFFAOYSA-N 0.000 description 1
- 238000001139 pH measurement Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000003756 stirring 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/022—Boron compounds without C-boron linkages
-
- 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
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
-
- 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"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1055—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with other heteroatoms
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Physics & Mathematics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Optics & Photonics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- 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)
Abstract
The invention discloses a kind of fluorescent probe molecule (I) for being used to detect alkaline pH, (prepared by the condensation reaction of the propionic acid of 4,4 difluoro, 4 boron 3a, 4a azepine cyclopentadiene acene 8 and m-aminophenol by compound 3 for the fluorescence probe.For the fluorescence probe to pH detection range 8.5 11.5, optimal detection range is 9.5 11.0.Molecule I preparation conditions of the present invention are gentle, and step is easy, and cost is low, has multiple hydrogen bond donors and acceptor in the molecular structure, can be adapted to the demand of aqueous assay, there is good application prospect.
Description
(1) technical field
The present invention relates to chemical analysis, field of bioanalysis, more particularly to a kind of fluorescence probe for detecting pH value and its conjunction
Into method and purposes.
(2) background technology
In recent years, a large amount of fluorescence probes are designed to be synthesized, and very strong detection instrument is provided for life science.
Because fluoroscopic examination has the advantages of easy to operate, to be adapted to living cells detection etc. notable, its application in biology obtains
Fast development.Measure pH most popular method has pH meter, pH test paper etc., and these methods have many offices in biosystem is applied to
Limit, so needing to design more efficient pH fluorescence probes, to detect applied to the pH in biosystem.
It is considerably less to detect the fluorescence probe of alkaline pH, this kind of probe such as lives in pH10.5 environment in research extreme microorganism
In microorganism (Bacillus pseudofirmus OF4 etc.), or microorganism in basic soil have it is very important
Value；Fluorescence probe can turn into the important component of the molecular device to pH sensings, so needing to develop some detection alkali
Property pH fluorescence probe, it can particularly cover the probe of this pH scope of 9.0-11.0.
(3) content of the invention
The technical problem to be solved in the present invention is that solve the deficiencies in the prior art, there is provided a kind of fluorescence for detecting alkaline ph values
Probe.
The technical solution adopted by the present invention is：
A kind of fluorescence probe, it is characterised in that the fluorescence probe has following structure formula (I)：
Above-mentioned fluorescence probe passes through compound 3- (4,4- bis- fluoro- 4- boron -3a, 4a- azepines-cyclopentadiene acene -8- propionic acid
Prepared by the condensation reaction of (Formula II) between m-aminophenol, reaction equation is as follows：
The solvent of the reaction can be dichloromethane, and condensing agent can be dicyclohexylcarbodiimide and 4- dimethylamino pyrroles
Pyridine, react at room temperature, there are two key reaction products, wherein non-blooming product component is probe I, the separation of routine can be passed through
Purification process, as column chromatographic isolation and purification obtains.
Above-mentioned fluorescence probe can be used for the detection and analysis of pH in chemical system or biosystem.
The method for using above-mentioned fluorescence probe detect pH comprises the following steps：
Fluorescence probe is dissolved in DMSO, is configured to detect liquid, concentration 1mM；Prepare the standard in pH8.0-pH12.0 sections
Solution, the above-mentioned μ L of detection liquid 1 are added in above-mentioned each standard liquid (1000 μ L), fluorescence intensity FI is determined after mixing, with
The logarithm (logFI) of fluorescence intensity is ordinate, and pH value is that standard curve is made in abscissa；It can be determined and treated according to standard curve
The pH of test sample product.
Above-mentioned fluorescence probe is 9.5-11.0 in 8.5-11.5, optimal detection range to pH detection range.
Molecule I preparation conditions of the present invention are gentle, and step is easy, and cost is low, has multiple hydrogen in the molecular structure
Key donor and acceptor atom, the demand of aqueous assay can be adapted to, there is good application prospect.
(4) illustrate
Fig. 1：At room temperature, in different pH solution, the fluorescence emission spectrum of probe (1 μM), ordinate is fluorescence intensity in figure,
Abscissa is launch wavelength.
Fig. 2：At room temperature, under different pH, the fluorescence intensity-pH curves of probe (1 μM), ordinate is that fluorescence is strong in figure
Degree, abscissa is pH value.
Fig. 3：According to standard curve made from the fluorescence intensity under different pH, ordinate is the logarithm of fluorescence intensity in figure
Value, abscissa is pH value.
Fig. 4：Probe (1 μM) is added to (right side) after pH8.5 solution (left side) and pH10.5 solution, shot under daylight light irradiation
Fluoroscopic image, show that probe sends macroscopic green fluorescence in alkaline solution.
(5) embodiment
Technical scheme is described further with specific embodiment below, but protection scope of the present invention is unlimited
In this：
Embodiment
The preferred embodiments of the present invention are illustrated below in conjunction with accompanying drawing, it will be appreciated that described herein preferred real
Apply example to be merely to illustrate and explain the present invention, be not intended to limit the present invention.
Embodiment 1：Prepare probe I：
By 3- (4,4- bis- fluoro- 4- boron -3a, 4a- azepines-cyclopentadiene acene -8- propionic acid (Formula II) (0.2mmol), two rings
Hexyl carbodiimide (0.2mmol), DMAP (0.02mmol), 3- amino-phenols (0.2mmol) are dissolved in drying
Dichloromethane in (20ml), stirring reaction 1 hour at room temperature, rotate solvent evaporated, can by the isolation and purification method of routine,
As column chromatography (petroleum ether: ethyl acetate=1 can be selected in eluant, eluent: 1) isolate and purify, key reaction product has two, wherein without
The component of fluorescence is probe I, obtains final product 2mg, yield 2.8%.HRMS(ESI)：m/z calcd for(C18H16BF2N3O2
+H)+：356.1382 found 356.1381.
Embodiment 2：Determine fluorescence emission spectrum of the fluorescence probe in different pH solution：
Different pH solution is prepared first, and probe is dissolved in into DMSO is added separately in above-mentioned solution again, makes probe
Final concentration of 1 μM.By its fluorescence intensity of fluorescent spectrophotometer assay, accompanying drawing 1 can be clearly seen that, in pH9.0,
Probe solution does not almost have fluorescence.10.0 are increased to pH, the fluorescence intensity of fluorescence probe starts gradually to strengthen.Accompanying drawing 2
The probe can be drawn near pH10.36, the detection sensitivity highest of probe.
Embodiment 3：Standard curve determination pH is drawn using above-mentioned fluorescence probe
Fluorescence probe is dissolved in DMSO, is configured to detect liquid, concentration 1mM；Prepare the standard in pH8.5-pH12.0 sections
Solution, the above-mentioned μ L of detection liquid 1 are added in above-mentioned each standard liquid (1000 μ L), fluorescence intensity FI is determined after mixing, with
The logarithm (logFI) of fluorescence intensity is ordinate, and pH value is that standard curve (accompanying drawing 3) is made in abscissa；Can according to standard curve
To determine the pH of testing sample.
Embodiment 4：Fluorescence probe detects alkaline solution
Fluorescence is dissolved in DMSO, is configured to detect liquid, concentration 1mM；Probe is added to pH8.5 solution (left side) and pH10.5
(right side) (1 μM of final concentration) after solution, fluoroscopic image is shot under daylight light irradiation, it is visible that probe sends naked eyes in alkaline solution
Green fluorescence.
Claims (7)
1. a kind of fluorescence probe, it is characterised in that the fluorescence probe has following structure formula (I)：
2. a kind of synthetic method of fluorescence probe as claimed in claim 1, it is characterised in that (4,4- bis- is fluoro- by compound 3-
4- boron -3a, 4a- azepine-condensation reaction be prepared of the cyclopentadiene acene -8- propionic acid (Formula II) between m-aminophenol
Compound (I), reaction equation is as follows：
A kind of 3. synthetic method of fluorescence probe as claimed in claim 2, it is characterised in that the solvent of the reaction is dichloromethane,
Condensing agent is dicyclohexylcarbodiimide and DMAP, is reacted at room temperature, and main reaction product has two, wherein without glimmering
The component of light is probe I, and reaction product isolates and purifies to obtain by conventional isolation and purification method such as column chromatography etc..
4. a kind of purposes of fluorescence probe as claimed in claim 1, it is characterised in that for pH in chemical system or biosystem
Detection and analysis.
A kind of 5. method for the detection pH for realizing purposes as claimed in claim 4, it is characterised in that comprise the following steps：
Fluorescence probe is dissolved in DMSO, is configured to detect liquid, concentration 1mM；The standard liquid in pH8.0-pH12.0 sections is prepared,
The above-mentioned μ L of detection liquid 1 are added in above-mentioned each standard liquid (1000 μ L), measure fluorescence intensity FI, strong with fluorescence after mixing
The logarithm (logFI) of degree is ordinate, and pH value is that standard curve is made in abscissa；Testing sample can be determined according to standard curve
PH.
6. a kind of purposes of fluorescence probe as claimed in claim 4, it is characterised in that the detection range of the pH is in 8.5-11.5.
7. a kind of purposes of fluorescence probe as claimed in claim 4, it is characterised in that the detection range of the pH is in 9.5-11.0.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711067277.6A CN107840855B (en) | 2017-11-02 | 2017-11-02 | fluorescent probe and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711067277.6A CN107840855B (en) | 2017-11-02 | 2017-11-02 | fluorescent probe and application thereof |
Publications (2)
| Publication Number | Publication Date |
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| CN107840855A true CN107840855A (en) | 2018-03-27 |
| CN107840855B CN107840855B (en) | 2019-12-13 |
Family
ID=61680735
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201711067277.6A Active CN107840855B (en) | 2017-11-02 | 2017-11-02 | fluorescent probe and application thereof |
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| Country | Link |
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| CN (1) | CN107840855B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111253420A (en) * | 2018-12-03 | 2020-06-09 | 中国科学院化学研究所 | Pyrene compound pH value fluorescent probe and preparation method and application thereof |
Citations (8)
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|---|---|---|---|---|
| CN101550156A (en) * | 2009-05-14 | 2009-10-07 | 浙江大学 | Fluorescence probe, synthetic method and uses thereof |
| CN102391854A (en) * | 2011-08-03 | 2012-03-28 | 浙江大学 | Fluorescent chemical sensor for detecting [H plus] and preparation method and usage thereof |
| CN103575714A (en) * | 2013-11-04 | 2014-02-12 | 广东工业大学 | Application of coumarone quinoline compound as difunctional pH probe |
| CN104531139A (en) * | 2015-01-06 | 2015-04-22 | 山西大学 | Carbazole type pH fluorescence probe and preparation method and application thereof |
| CN105548174A (en) * | 2015-12-04 | 2016-05-04 | 贵州大学 | Method using light on/off mode probe to measure solution pH |
| CN106083816A (en) * | 2016-07-06 | 2016-11-09 | 山西大学 | A kind of extremely acid carbazoles pH fluorescent probe and its preparation method and application |
| CN106483113A (en) * | 2016-10-26 | 2017-03-08 | 华南师范大学 | 1 pyrene formic acid is used as the application of pH fluorescence probe |
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-
2017
- 2017-11-02 CN CN201711067277.6A patent/CN107840855B/en active Active
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111253420A (en) * | 2018-12-03 | 2020-06-09 | 中国科学院化学研究所 | Pyrene compound pH value fluorescent probe and preparation method and application thereof |
| CN111253420B (en) * | 2018-12-03 | 2021-05-04 | 中国科学院化学研究所 | Pyrene compound pH value fluorescent probe and preparation method and application thereof |
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| Publication number | Publication date |
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| CN107840855B (en) | 2019-12-13 |
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