CN114573625B - BOPYIN fluorescent probe with acid response and preparation method thereof - Google Patents
BOPYIN fluorescent probe with acid response and preparation method thereof Download PDFInfo
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- 239000002253 acid Substances 0.000 title claims abstract description 39
- 239000007850 fluorescent dye Substances 0.000 title claims abstract description 13
- 238000002360 preparation method Methods 0.000 title abstract description 5
- 239000000523 sample Substances 0.000 claims abstract description 11
- 239000007788 liquid Substances 0.000 claims abstract description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 142
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 140
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 138
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 119
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 57
- 239000002953 phosphate buffered saline Substances 0.000 claims description 47
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 42
- 229910017604 nitric acid Inorganic materials 0.000 claims description 42
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 38
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 36
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 27
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 23
- 239000000243 solution Substances 0.000 claims description 23
- 229940126214 compound 3 Drugs 0.000 claims description 14
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 12
- 238000004440 column chromatography Methods 0.000 claims description 12
- 229940125904 compound 1 Drugs 0.000 claims description 11
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 7
- 235000019270 ammonium chloride Nutrition 0.000 claims description 6
- 239000012295 chemical reaction liquid Substances 0.000 claims description 6
- 229940125782 compound 2 Drugs 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 4
- BVDLHLPSFYRKIC-UHFFFAOYSA-N N1C=CC=C1.N1C=CC=C1.[B] Chemical compound N1C=CC=C1.N1C=CC=C1.[B] BVDLHLPSFYRKIC-UHFFFAOYSA-N 0.000 claims description 3
- -1 compound 2 Chemical compound 0.000 claims description 3
- 238000010898 silica gel chromatography Methods 0.000 claims description 2
- 239000012265 solid product Substances 0.000 claims description 2
- 238000010025 steaming Methods 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- 238000000746 purification Methods 0.000 abstract description 9
- 238000000926 separation method Methods 0.000 abstract description 3
- 150000007513 acids Chemical class 0.000 abstract description 2
- 238000001308 synthesis method Methods 0.000 abstract description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 238000005810 carbonylation reaction Methods 0.000 abstract 1
- 238000006114 decarboxylation reaction Methods 0.000 abstract 1
- 239000011259 mixed solution Substances 0.000 description 61
- 238000002189 fluorescence spectrum Methods 0.000 description 18
- FEIOASZZURHTHB-UHFFFAOYSA-N methyl 4-formylbenzoate Chemical compound COC(=O)C1=CC=C(C=O)C=C1 FEIOASZZURHTHB-UHFFFAOYSA-N 0.000 description 10
- 239000012452 mother liquor Substances 0.000 description 9
- 239000010413 mother solution Substances 0.000 description 9
- 238000001514 detection method Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 230000035484 reaction time Effects 0.000 description 5
- 238000005303 weighing Methods 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000003935 benzaldehydes Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000001788 irregular Effects 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 206010001029 Acute pulmonary oedema Diseases 0.000 description 1
- 208000009043 Chemical Burns Diseases 0.000 description 1
- LIQLLTGUOSHGKY-UHFFFAOYSA-N [B].[F] Chemical group [B].[F] LIQLLTGUOSHGKY-UHFFFAOYSA-N 0.000 description 1
- 230000037374 absorbed through the skin Effects 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 206010069351 acute lung injury Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 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
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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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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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
- C09K2211/1018—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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- 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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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Life Sciences & Earth Sciences (AREA)
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Abstract
The application discloses a conjugated BOPYAIN fluorescent probe with acid response and a preparation method thereof, the structure can detect various acids in a liquid environment, and the structure of the fluorescent probe is as follows:
Description
Technical Field
The application discloses a BOPYIN fluorescent probe with acid response and a preparation method thereof, wherein the probe can distinguish the molar quantity of acid through different fluorescence intensities, and can detect the change of the molar quantity of acid in various liquid environments.
Background
Hydrochloric acid is a volatile acid and toxic. If a large amount of concentrated hydrochloric acid is inhaled or taken by mistake, the phenomenon of airway mucous membrane damage can occur, and acute lung injury can occur seriously. Trifluoroacetic acid is a volatile acid that can be harmful to the body if inhaled or absorbed through the skin. Sulfuric acid is a strong acid and if inadvertently contacted with sulfuric acid, chemical burns may result, the risk of which increases with increasing sulfuric acid concentration. Nitric acid is a strong volatile acid that if inhaled can irritate the respiratory tract causing acute pulmonary edema. Burns may be caused if the eyes are in contact with the skin.
Most of the existing methods for realizing acid detection by using different fluorescent probes have the defects of complex operation method, long reaction time, low sensitivity and the like. Therefore, a detection method that is simple to operate, rapid to detect, and capable of highly sensitive identification of acids is needed.
Disclosure of Invention
In order to solve the above problems, the present application provides an acid-responsive bopylin fluorescent probe which has strong acid sensitivity and can distinguish the molar amount of acid by different fluorescence intensities in various liquid environments, and has a molecular formula of C 26 H 24 BF 2 N 3 O 2 The structural formula is as follows:
the synthesis method of the fluorescent probe comprises the following synthesis paths:
(1) Adding a seven-membered boron dipyrrole compound 1 and toluene into a reaction bottle at room temperature, adding a compound 2, piperidine and acetic acid, and heating and refluxing to obtain a reaction liquid 1;
(2) Spin-steaming the reaction liquid 1 in the step (1), and separating by silica gel column chromatography to obtain a solid product 3;
(3) Respectively adding tetrahydrofuran, methanol, ammonium chloride and zinc into the compound 3 in the step (2), and carrying out heating reflux reaction to obtain a reaction solution 2;
(4) And (3) respectively washing, extracting, drying, performing column chromatography and spin-drying the reaction liquid 2 in the step (3) to obtain a green solid compound I.
In the step (1), the compound 2 is para-position derivative of benzaldehyde, and the feeding mole ratio of the seven-membered fluoroborodipyrrole compound to the para-position derivative of benzaldehyde is 1:1-10.
The feeding sequence of the step (1) is seven-membered boron dipyrrole fluoride compound, toluene, compound 2, piperidine and acetic acid; the feeding ratio of the compound 1 to the piperidine to the acetic acid is 1:1-10:1-10.
The heating temperature of the step (1) is 100-140 ℃ and the heating time is 6-12 hours.
The application applies the prepared fluorescent probe to the detection of hydrochloric acid, trifluoroacetic acid, sulfuric acid and nitric acid in a liquid environment.
The liquid environment comprises one or more of water, ethanol, acetonitrile, PBS and DMSO.
The application has the following beneficial effects:
(1) The probe of the application has obvious response to acid and is stable under neutral or acidic conditions, which indicates that the compound can be used as a probe for detecting the acid content.
(2) The fluorescence probe with the fluorine-boron structure can distinguish the molar quantity of the acid through different fluorescence intensities, so that the change of the molar quantity of the acid in the liquid environment can be detected. The molar ratio of the probe to the hydrochloric acid detection limit is 1:1.67-16.67 (volume ratio of PBS to DMSO is 5:5), the molar ratio of the probe to trifluoroacetic acid detection limit is 1:1.67-38.33 (volume ratio of PBS to DMSO is 6:4), the molar ratio of the probe to the sulfuric acid limit is 1:1.67-21.67 (water to DMSO volume ratio 9:1), the molar ratio of probe to nitric acid limit of detection is 1:1.67-10 (water to DMSO volume ratio 5:5).
(3) The probe reaction condition is mild, easy to control and simple in product purification.
Drawings
FIG. 1 is a hydrogen spectrum of compound I obtained in example 1.
FIG. 2 is a mass spectrum of compound I obtained in example 1.
FIG. 3 is a hydrogen spectrum of compound 3 obtained in example 1.
FIG. 4 is a fluorescence spectrum of compound I obtained in example 6 titrated with hydrochloric acid in DMSO solution.
FIG. 5 is a fluorescence spectrum of compound I obtained in example 6 titrated with hydrochloric acid in a mixed solution of PBS and DMSO in a volume ratio of 5:5.
FIG. 6 is a fluorescence spectrum of compound I obtained in example 7 titrated with trifluoroacetic acid in acetonitrile.
FIG. 7 is a fluorescence spectrum of compound I obtained in example 7 titrated with trifluoroacetic acid in a mixed solution of PBS and DMSO in a volume ratio of 6:4.
FIG. 8 is a fluorescence spectrum of compound I obtained in example 8 titrated with sulfuric acid in DMSO solution.
FIG. 9 is a plot of the volume ratio of water to DMSO for compound I obtained in example 8 at 9:1 to a sulfuric acid titration.
FIG. 10 is a fluorescence spectrum of the compound I obtained in example 9 titrated with nitric acid in ethanol solution.
FIG. 11 is a fluorescence spectrum of compound I obtained in example 9 titrated with nitric acid in a mixed solution with a water to DMSO volume ratio of 5:5.
Detailed Description
The present application will be further illustrated by the following examples, but the scope of the application is not limited to the examples.
Example 1
Compound 1 (686 mg,2 mmol) was weighed, 60.00mL of toluene was mixed and dissolved, methyl p-formylbenzoate (328 mg,2 mmol), piperidine (0.18 mL,2 mmol), acetic acid (0.12 mL,2 mmol) and heated at 100 ℃ for 12 hours to complete the reaction, the reaction was distilled off, and the compound 3 (303.2 mg, 31.3% yield) was obtained after purification by column chromatography. Compound 3 (4819 mg,1 mmol) was weighed and dissolved in 40.0mL of DCM solution, then zinc powder (325 mg,5 mmol) was slowly added, the reaction was stirred for 2 hours at 35 ℃ and completed, the reaction was extracted, dried by spin, and after column chromatography separation and purification, green solid I (137.6 mg, yield 31%) was obtained, molecular formula was C 26 H 24 BF 2 N 3 O 2 The structural formula is
Example 2
Compound 1 (686 mg,2 mmol) was weighed, 60.00mL of toluene was mixed and dissolved, methyl p-formylbenzoate (650 mg,4 mmol), piperidine (0.18 mL,2 mmol), acetic acid (0.12 mL,2 mmol) and heated at 100 ℃ for 10 hours to complete the reaction, the reaction was distilled off, and the compound 3 (772.6 mg, yield 81.5%) was obtained after purification by column chromatography. When the amount of methyl paraformylbenzoate was increased 2 times as compared with example 1, the yield was increased by 50.2%, and the reaction time was shortened by 2 hours. Compound 3 (489 mg,1 mmol) was weighed and dissolved in 40.0mL of a mixture of DCM and MeOH (volume ratio of DCM to MeOH is 1:1), zinc powder (325 mg,5 mmol) was slowly added thereto, and the mixture was heated and stirred at 35 ℃ for 2 hours to complete the reaction, the reaction was extracted, dried by spin-drying, and separated and purified by column chromatography to obtainTo green solid I (207.5 mg, 45.2% yield), formula C 26 H 24 BF 2 N 3 O 2 The structural formula isWhen the solvent was changed to a mixture of DCM and MeOH (volume ratio of DCM to MeOH: 1), the yield was increased by 14.2% compared to example 1.
Example 3
Compound 1 (686 mg,2 mmol) was weighed, 60.00mL of toluene was mixed and dissolved, methyl p-formylbenzoate (650 mg,4 mmol), piperidine (0.36 mL,4 mmol), acetic acid (0.24 mL,4 mmol) were sequentially added, the reaction was stirred for 10 hours at 100 ℃ and heated to complete the reaction, the reaction was distilled off, and after purification by column chromatography, compound 3 (351.7 mg, 37.1% yield) was obtained. When the amount of piperidine, acetic acid was increased 2-fold with respect to example 2, the yield was not significantly changed. Compound 3 (489 mg,1 mmol) was weighed into 40.0mL of a mixture of DCM and MeOH (volume ratio of DCM to MeOH: 1:1), zinc powder (325 mg,5 mmol), ammonium chloride (267.5 mg,5 mmol) was slowly added thereto, the mixture was heated and stirred at 35 ℃ for 2 hours to complete the reaction, the reaction was extracted, dried by spinning, and the green solid I (342.4 mg, yield 74.6%) was obtained after separation and purification by column chromatography, molecular formula C 26 H 24 BF 2 N 3 O 2 The structural formula isWhen ammonium chloride was added to the system in an amount equivalent to 3 times the molar amount of the compound, the yield was improved by 32.1% as compared with example 2.
Example 4
Compound 1 (686 mg,2 mmol) was weighed, 60.00mL of toluene was mixed and dissolved, methyl p-formylbenzoate (650 mg,4 mmol), piperidine (0.18 mL,2 mmol), acetic acid (0.12 mL,2 mmol) and heated at 120 ℃ for 6 hours to complete the reaction, the reaction was distilled off, and the compound 3 (811.5 mg, yield 85.6%) was obtained after purification by column chromatography. When the reaction temperature was increased by 20℃corresponding to example 2, the yield was increased by 4.1%, and the reaction time was shortened by 4 hours. Compound 3 (489 mg,1 mmol) was weighed out in 40.0mL of DCM and MeOHTo the mixture of DCM and MeOH in a volume ratio of 1:2, zinc powder (325 mg,5 mmol), ammonium chloride (267.5 mg,5 mmol) and stirring at 35 deg.C for 2 hr to complete the reaction, extracting the reaction, spin drying, and separating and purifying by column chromatography to obtain green solid I (273.6 mg, 59.6% yield) with molecular formula of C 26 H 24 BF 2 N 3 O 2 The structural formula isWhen the volume ratio of DCM to MeOH in the solvent was changed from 1:1 to 1:2, the yield was reduced by 15% compared to example 3.
Example 5
Compound 1 (686 mg,2 mmol) was weighed, 60.00mL of toluene was mixed and dissolved, methyl p-formylbenzoate (650 mg,4 mmol), piperidine (0.18 mL,2 mmol), acetic acid (0.12 mL,2 mmol) was added sequentially, the mixture was heated and stirred at 140 ℃ for 6 hours to complete the reaction, the reaction was distilled off, and the compound 3 (681.6 mg, yield 71.9%) was obtained after purification by column chromatography. When the reaction temperature was increased by 20℃corresponding to example 2, the yield was reduced by 9.6%, and the reaction time was shortened by 4 hours. Compound 3 (489 mg,1 mmol) was weighed into a 40.0mL mixture of DCM and MeOH (volume ratio of DCM to MeOH: 1:1), zinc powder (650 mg,10 mmol), amine chloride (535 mg,10 mmol) were slowly added, the reaction was stirred for 1.5 hours at 35℃until complete, the reaction was extracted, dried by spinning, and the column chromatography was separated and purified to give green solid I (345.2 mg, yield 75.2%) of formula C 26 H 24 BF 2 N 3 O 2 The structural formula isWhen the amounts of zinc powder and ammonium chloride were increased 2 times as compared with example 3, the yield was not significantly changed, and the reaction time was shortened by 0.5 hour.
Example 6
Compound I (3.4 mg,0.01 mmol) was weighed, 1mL of acetonitrile was added to dissolve and prepare a mother liquor of 0.01mol/L, then 6 μl of the mother liquor was respectively dissolved in 3mL of distilled water, 3mL of ethanol, 3mL of acetonitrile, 3mL of dimethyl sulfoxide to prepare a solution to be measured of 20 μmol/L, and then 0.01mol/L of hydrochloric acid was successively added dropwise to the solution to be measured (each time, 10 μl was added dropwise until the fluorescence intensity no longer increased or decreased), and the change of the fluorescence spectrum was detected, respectively. It can be observed that the fluorescence intensity increases with increasing molar amount of acid. Taking the example in DMSO solvent, the peak at 589nm is stepped up to a concentration of 0.01mol/L hydrochloric acid, 10. Mu.L is added for the first time, followed by 10. Mu.L each time, until a total of 70. Mu.L is added. When the total amount of hydrochloric acid was added to 70. Mu.L, i.e., 0.7. Mu. Mol, the fluorescence intensity was not increased any more, giving FIG. 4. Meanwhile, the mother solution is added with 0.01mol/L hydrochloric acid in water, and the peak value at 558nm is increased along with the increase of the molar quantity of the hydrochloric acid; adding 0.01mol/L hydrochloric acid into ethanol, wherein the peak value at 563nm increases with the increase of the molar quantity of the hydrochloric acid; hydrochloric acid was added to acetonitrile in an amount of 0.01mol/L, and the peak at 559nm increased with an increase in the molar amount of hydrochloric acid.
Weighing compound I (3.4 mg,0.01 mmol), adding 1mL of acetonitrile, dissolving to prepare a mother solution of 0.01mol/L, and then dissolving 6 mu L of mother solution into 3mL of mixed solution, wherein the mixed solution is prepared by mixing water and DMSO in a volume ratio of 9:1 or 8:2 or 7:3 or 6:4 or 5:5 respectively; the ratio of PBS to DMSO volume is 9:1 or 8:2 or 7:3 or 6:4 or 5:5; the volume ratio of water to ethanol is 9:1 or 8:2 or 7:3 or 6:4 or 5:5; the volume ratio of PBS to ethanol is 9:1 or 8:2 or 7:3 or 6:4 or 5:5; the ratio of water to acetonitrile volume is 9:1 or 8:2 or 7:3 or 6:4 or 5:5; the volume ratio of PBS to acetonitrile is 9:1 or 8:2 or 7:3 or 6:4 or 5:5, a 20 mu mol/L solution to be detected is prepared, then 0.01mol/L hydrochloric acid is gradually dripped into the solution to be detected (10 mu L is dripped each time until the fluorescence intensity is not increased or reduced any more), and the change of the fluorescence spectrum is detected respectively. It was observed that the fluorescence intensity increased with increasing molar amount of acid in the mixed solution with a 5:5 ratio of PBS to DMSO volume, and that the fluorescence intensity did not increase or decrease gradually in the remaining 29 mixed solutions. In the fluorescence spectrum of the mixed solution with a volume ratio of PBS to DMSO of 5:5, the peak at 626nm was gradually increased, the concentration of hydrochloric acid was 0.01mol/L, 10. Mu.L was added for the first time, followed by 10. Mu.L each time, until a total of 100. Mu.L was added. When the total amount of hydrochloric acid was added to 100. Mu.L, i.e., 1. Mu. Mol, the fluorescence intensity was not increased any more, giving FIG. 5.
Example 7
Compound I (3.4 mg,0.01 mmol) was weighed, 1mL of acetonitrile was added to dissolve and prepare a mother liquor of 0.01mol/L, then 6 μl of the mother liquor was dissolved in 3mL of distilled water, ethanol, acetonitrile and dimethyl sulfoxide, respectively, to prepare a solution to be measured of 20 μmol/L, and then 0.01mol/L of trifluoroacetic acid was gradually added dropwise to the solution to be measured (each time, 10 μl was added dropwise until the fluorescence intensity no longer increased or decreased), and the change of the fluorescence spectrum was detected, respectively. It can be observed that the fluorescence intensity increases with increasing molar amount of acid. Taking the example in acetonitrile solution, the peak at 585nm is gradually raised, the concentration of trifluoroacetic acid is 0.01mol/L, 10. Mu.L is added for the first time, followed by 10. Mu.L each time, until 190. Mu.L in total is added. When the total amount of trifluoroacetic acid was added to 190. Mu.L, i.e., 1.9. Mu. Mol, the fluorescence intensity was no longer increased, giving FIG. 6. The peak at 609nm of the addition of 0.01mol/L trifluoroacetic acid to water increased with the increase in the molar amount of trifluoroacetic acid. The peak at 611nm increased with increasing molar amount of trifluoroacetic acid by adding 0.01mol/L trifluoroacetic acid to DMSO. The peak at 615nm of 0.01mol/L trifluoroacetic acid added to ethanol increased with increasing molar amount of trifluoroacetic acid.
Weighing compound I (3.4 mg,0.01 mmol), dissolving 1mL of acetonitrile to prepare 0.01mol/L mother liquor, and dissolving 6 mu L of mother liquor into 3mL of mixed solution, wherein the mixed solution is prepared by mixing water and DMSO in a volume ratio of 9:1 or 8:2 or 7:3 or 6:4 or 5:5 respectively; the ratio of PBS to DMSO volume is 9:1 or 8:2 or 7:3 or 6:4 or 5:5; the volume ratio of water to ethanol is 9:1 or 8:2 or 7:3 or 6:4 or 5:5; the volume ratio of PBS to ethanol is 9:1 or 8:2 or 7:3 or 6:4 or 5:5; the ratio of water to acetonitrile volume is 9:1 or 8:2 or 7:3 or 6:4 or 5:5; the volume ratio of PBS to acetonitrile is 9:1 or 8:2 or 7:3 or 6:4 or 5:5, 20 mu mol/L of solution to be detected is prepared, 0.01mol/L of trifluoroacetic acid is gradually dripped into the solution to be detected (10 mu L is dripped each time until the fluorescence intensity is not increased or reduced), and the change of the fluorescence spectrum is detected respectively. It can be observed that the ratio between the volumes of PBS and DMSO is 6:4, the fluorescence intensity in the mixed solution increases with the increase of the molar amount of the acid, and the fluorescence intensity in the other 29 mixed solutions does not change. The ratio of PBS to DMSO volume is 6:4, the peak at 582nm was gradually increased, the concentration of trifluoroacetic acid was 0.01mol/L, 10. Mu.L was added for the first time, followed by 10. Mu.L each time, until a total of 230. Mu.L was added. When the total amount of trifluoroacetic acid was added to 230. Mu.L, i.e., 2.3. Mu. Mol, the fluorescence intensity was no longer increased, giving FIG. 7.
Example 8
Compound I (3.4 mg,0.01 mmol) was weighed, 1mL of acetonitrile was added to dissolve and prepare a mother liquor of 0.01mol/L, then 6 μl of the mother liquor was dissolved in 3mL of distilled water, ethanol, acetonitrile, dimethyl sulfoxide, respectively, to prepare a solution to be measured of 20 μmol/L, and then 0.01mol/L of sulfuric acid was added thereto, respectively (10 μl was added dropwise each time until the fluorescence intensity was no longer increased or decreased), and the change of the fluorescence spectrum thereof was detected, respectively. It can be observed that the fluorescence intensity increases with increasing molar amount of acid. Taking the example in DMSO solution, the peak at 589nm was gradually increased, and when the total amount of sulfuric acid was added to 70. Mu.L, i.e., 0.7. Mu. Mol, the fluorescence intensity was no longer increased, giving FIG. 8. The mother liquor of this example was used to add 0.01mol/L sulfuric acid to water, the peak at 605nm increasing with increasing molar amount of sulfuric acid; adding 0.01mol/L sulfuric acid to ethanol, wherein the peak value at 607nm increases with the increase of the molar amount of sulfuric acid; the peak at 607nm increases with increasing molar amount of sulfuric acid by adding 0.01mol/L sulfuric acid to acetonitrile.
Weighing compound I (3.4 mg,0.01 mmol), adding 1mL of acetonitrile, dissolving to prepare a mother solution of 0.01mol/L, and then dissolving 6 mu L of mother solution into 3mL of mixed solution, wherein the mixed solution is prepared by mixing water and DMSO in a volume ratio of 9:1 or 8:2 or 7:3 or 6:4 or 5:5 respectively; the ratio of PBS to DMSO volume is 9:1 or 8:2 or 7:3 or 6:4 or 5:5; the volume ratio of water to ethanol is 9:1 or 8:2 or 7:3 or 6:4 or 5:5; the volume ratio of PBS to ethanol is 9:1 or 8:2 or 7:3 or 6:4 or 5:5; the ratio of water to acetonitrile volume is 9:1 or 8:2 or 7:3 or 6:4 or 5:5; the volume ratio of PBS to acetonitrile is 9:1 or 8:2 or 7:3 or 6:4 or 5:5, a solution to be detected of 20 mu mol/L is prepared, and then 0.01mol/L sulfuric acid is respectively added (10 mu L is added dropwise each time until the fluorescence intensity is no longer increased or reduced) to respectively detect the change of the fluorescence spectrum. It can be observed that the fluorescence intensity in three mixed solutions, namely, 5:5 water to DMSO volume ratio, 6:4 PBS to DMSO volume ratio and 5:5 PBS to DMSO volume ratio, does not gradually increase or decrease with the increase of the molar amount of the acid, but shows irregular changes and cannot be used as a reagent for detecting the acid; the rest 27 mixed solutions have strong fluorescence intensity at the corresponding wavelength, and the fluorescence intensity is increased along with the increase of the molar quantity of the acid, so that the mixed solutions show regular change and can be used as detection reagents. Taking as an example a mixed solution with a water to DMSO volume ratio of 9:1, fig. 9 is obtained. It was observed that as the amount of acid increased, the peak at 753nm in the fluorescence spectrum was gradually increased, the concentration of sulfuric acid was 0.01mol/L, 10. Mu.L was added for the first time, followed by 10. Mu.L each time, until 130. Mu.L was added in total. When the total amount of sulfuric acid was added to 130. Mu.L, i.e., 1.3. Mu. Mol, the fluorescence intensity was not increased any more. To a mixed solution of water and DMSO in a volume ratio of 8:2, 0.01mol/L sulfuric acid was added, and the peak at 548nm increased with increasing molar amount of sulfuric acid. To a mixed solution having a volume ratio of water to DMSO of 7:3, 0.01mol/L sulfuric acid was added, and the peak at 550nm increased with increasing molar amount of sulfuric acid. To a mixed solution of water and DMSO in a volume ratio of 6:4, 0.01mol/L sulfuric acid was added, and the peak at 555nm increased with increasing molar amount of sulfuric acid. To a mixed solution of PBS and DMSO in a volume ratio of 9:1, 0.01mol/L sulfuric acid was added, and the peak at 549nm increased with increasing molar amount of sulfuric acid. To a mixed solution of PBS and DMSO in a volume ratio of 8:2, 0.01mol/L sulfuric acid was added, and the peak at 552nm increased with increasing molar amount of sulfuric acid. To a mixed solution of PBS and DMSO in a volume ratio of 7:3, 0.01mol/L sulfuric acid was added, and the peak at 556nm increased with increasing molar amount of sulfuric acid. To a mixed solution of water and ethanol in a volume ratio of 9:1, 0.01mol/L sulfuric acid was added, and the peak at 547nm increased with increasing molar amount of sulfuric acid. To a mixed solution of water and ethanol in a volume ratio of 8:2, 0.01mol/L sulfuric acid was added, and the peak at 551nm increased with increasing molar amount of sulfuric acid. To a mixed solution of water and ethanol in a volume ratio of 7:3, 0.01mol/L sulfuric acid was added, and the peak at 555nm increased with increasing molar amount of sulfuric acid. To a mixed solution having a volume ratio of water to ethanol of 6:4, 0.01mol/L sulfuric acid was added, and a peak at 544nm increased with an increase in the molar amount of sulfuric acid. To a mixed solution of water and ethanol in a volume ratio of 5:5, 0.01mol/L sulfuric acid was added, and the peak at 559nm increased with increasing molar amount of sulfuric acid. In the mixed solution with the volume ratio of PBS to ethanol of 9:1, 0.01mol/L sulfuric acid is added, the peak value at 547nm increases with the increase of the molar amount of the sulfuric acid, in the mixed solution with the volume ratio of PBS to ethanol of 8:2, 0.01mol/L sulfuric acid is added, and the peak value at 550nm increases with the increase of the molar amount of the sulfuric acid. To a mixed solution of PBS and ethanol in a volume ratio of 7:3, 0.01mol/L sulfuric acid was added, and the peak at 548nm increased with increasing molar amount of sulfuric acid. To a mixed solution of PBS and ethanol in a volume ratio of 6:4, 0.01mol/L sulfuric acid was added, and the peak at 545nm increased with increasing molar amount of sulfuric acid. To a mixed solution of PBS and ethanol in a volume ratio of 5:5, 0.01mol/L sulfuric acid was added, and a peak at 549nm increased with an increase in the molar amount of sulfuric acid. To a mixed solution having a volume ratio of water to acetonitrile of 9:1, 0.01mol/L of sulfuric acid was added, and a peak at 613nm increased with an increase in the molar amount of sulfuric acid. To a mixed solution having a volume ratio of water to acetonitrile of 8:2, 0.01mol/L of sulfuric acid was added, and the peak at 622nm increased with an increase in the molar amount of sulfuric acid. To a mixed solution having a volume ratio of water to acetonitrile of 7:3, 0.01mol/L of sulfuric acid was added, and a peak at 611nm increased with an increase in the molar amount of sulfuric acid. To a mixed solution having a volume ratio of water to acetonitrile of 6:4, 0.01mol/L of sulfuric acid was added, and a peak at 607nm increased with an increase in the molar amount of sulfuric acid. To a mixed solution having a volume ratio of water to acetonitrile of 5:5, 0.01mol/L of sulfuric acid was added, and the peak at 609nm increased with an increase in the molar amount of sulfuric acid. To a mixed solution of PBS and acetonitrile in a volume ratio of 9:1, 0.01mol/L sulfuric acid was added, and the peak at 607nm increased with an increase in the molar amount of sulfuric acid. To a mixed solution of PBS and acetonitrile in a volume ratio of 8:2, 0.01mol/L sulfuric acid was added, and the peak at 610nm increased with increasing molar amount of sulfuric acid. To a mixed solution of PBS and acetonitrile in a volume ratio of 7:3, 0.01mol/L sulfuric acid was added, and the peak at 611nm increased with an increase in the molar amount of sulfuric acid. To a mixed solution of PBS and acetonitrile in a volume ratio of 6:4, 0.01mol/L sulfuric acid was added, and the peak at 607nm increased with an increase in the molar amount of sulfuric acid. To a mixed solution of PBS and acetonitrile in a volume ratio of 5:5, 0.01mol/L sulfuric acid was added, and the peak at 609nm increased with an increase in the molar amount of sulfuric acid.
Example 9
Weighing compound I (3.4 mg,0.01 mmol), adding 1mL of acetonitrile, dissolving to prepare a mother solution of 0.01mol/L, then dissolving 6 mu L of mother solution into 3mL of distilled water, ethanol, acetonitrile and dimethyl sulfoxide respectively to prepare a solution to be tested of 20 mu mol/L, adding 0.01mol/L of nitric acid into the solution (10 mu L is added dropwise each time until the fluorescence intensity is no longer increased or reduced), and detecting the change of the fluorescence spectrum of the solution. It can be observed that the fluorescence intensity increases with increasing molar amount of acid. Taking the example in ethanol solution, the 584nm peak is stepped up to a nitric acid concentration of 0.01mol/L, 10. Mu.L is added for the first time, followed by 10. Mu.L each time, until a total of 40. Mu.L is added. When the total amount of nitric acid was added to 40. Mu.L, i.e., 0.4. Mu. Mol, the fluorescence intensity was not increased any more, giving FIG. 10. The peak at 580nm increases with increasing molar amount of nitric acid by adding 0.01mol/L nitric acid to water. The peak at 585nm increased with increasing molar amount of nitric acid by adding 0.01mol/L nitric acid to DMSO. The peak at 589nm increases with increasing molar amount of nitric acid by adding 0.01mol/L nitric acid to acetonitrile.
Weighing compound I (3.4 mg,0.01 mmol), adding 1mL of acetonitrile, dissolving to prepare a mother solution of 0.01mol/L, and then dissolving 6 mu L of mother solution into 3mL of mixed solution, wherein the mixed solution is prepared by mixing water and DMSO in a volume ratio of 9:1 or 8:2 or 7:3 or 6:4 or 5:5 respectively; the ratio of PBS to DMSO volume is 9:1 or 8:2 or 7:3 or 6:4 or 5:5; the volume ratio of water to ethanol is 9:1 or 8:2 or 7:3 or 6:4 or 5:5; the volume ratio of PBS to ethanol is 9:1 or 8:2 or 7:3 or 6:4 or 5:5; the ratio of water to acetonitrile volume is 9:1 or 8:2 or 7:3 or 6:4 or 5:5; the volume ratio of PBS to acetonitrile is 9:1 or 8:2 or 7:3 or 6:4 or 5:5, a 20 mu mol/L solution to be detected is prepared, then 0.01mol/L nitric acid is respectively added (10 mu L is added dropwise each time until the fluorescence intensity is no longer increased or reduced), and the change of the fluorescence spectrum is respectively detected. It can be observed that the fluorescence intensity increases with increasing molar amount of acid in the mixed solution of water to DMSO volume ratio of 9:1, water to DMSO volume ratio of 5:5, water to ethanol volume ratio of 9:1, water to ethanol volume ratio of 7:3, water to ethanol volume ratio of 6:4, water to acetonitrile volume ratio of 5:5, water to acetonitrile volume ratio of 9:1, water to acetonitrile volume ratio of 7:3, PBS to DMSO volume ratio of 7:3, PBS to ethanol volume ratio of 6:4, PBS to ethanol volume ratio of 5:5, PBS to acetonitrile volume ratio of 8:2, PBS to acetonitrile volume ratio of 7:3, and the fluorescence intensity does not increase or decrease with increasing molar amount of acid in the remaining 17 mixed solutions, but shows irregular variation, and cannot be used as a detection reagent. Taking as an example a mixed solution with a water to DMSO volume ratio of 9:1, fig. 11 is obtained. It was observed that the peak at 558nm in the fluorescence spectrum was gradually increased with increasing amount of acid, the concentration of nitric acid being 0.01mol/L, 10. Mu.L being added for the first time, followed by 10. Mu.L each time, until a total of 60. Mu.L was added. When the total amount of nitric acid was added to 60. Mu.L, i.e., 0.6. Mu. Mol, the fluorescence intensity was not increased any more. To a mixed solution of water and DMSO in a volume ratio of 5:5 was added 0.01mol/L nitric acid, and the peak at 541nm increased with increasing molar amount of nitric acid. 0.01mol/L nitric acid is added into the mixed solution with the volume ratio of water to ethanol being 9:1, and the peak value at 549nm is increased along with the increase of the molar quantity of the nitric acid. To a mixed solution of water and ethanol in a volume ratio of 7:3, 0.01mol/L nitric acid was added, and the peak at 551nm increased with an increase in the molar amount of nitric acid. To a mixed solution of water and ethanol in a volume ratio of 6:4, 0.01mol/L nitric acid was added, and the peak at 551nm increased with an increase in the molar amount of nitric acid. To a mixed solution of water and ethanol in a volume ratio of 5:5 was added 0.01mol/L nitric acid, and the peak at 553nm increased with increasing molar amount of nitric acid. To a mixed solution having a volume ratio of water to acetonitrile of 9:1 was added 0.01mol/L nitric acid, and a peak at 597nm increased with an increase in the molar amount of nitric acid. To a mixed solution having a volume ratio of water to acetonitrile of 7:3, 0.01mol/L of nitric acid was added, and the peak at 588nm increased with an increase in the molar amount of nitric acid. To a mixed solution of PBS and DMSO in a volume ratio of 7:3 was added 0.01mol/L nitric acid, and the peak at 550nm increased with increasing molar amount of nitric acid. To a mixed solution of PBS and ethanol in a volume ratio of 6:4 was added 0.01mol/L nitric acid, and the peak at 547nm increased with increasing molar amount of nitric acid. To a mixed solution of PBS and ethanol in a volume ratio of 5:5 was added 0.01mol/L nitric acid, and the peak at 550nm increased with an increase in the molar amount of nitric acid. To a mixed solution of PBS and acetonitrile in a volume ratio of 8:2 was added 0.01mol/L nitric acid, and a peak at 552nm increased with an increase in the molar amount of nitric acid. To a mixed solution of PBS and acetonitrile in a volume ratio of 7:3 was added 0.01mol/L nitric acid, and the peak at 552nm increased with an increase in the molar amount of nitric acid.
Claims (6)
1. A BOPYIN fluorescent probe with acid response is characterized in that the molecular formula of the probe is C 26 H 24 BF 2 N 3 O 2 The structure is as follows:
2. the method for preparing a bopylin fluorescent probe with an acid response according to claim 1, comprising the following steps:
(1) Adding a seven-membered boron dipyrrole compound 1 and toluene into a reaction bottle at room temperature, adding a compound 2, piperidine and acetic acid, and heating and refluxing to obtain a reaction liquid 1;
(2) Spin-steaming the reaction liquid 1 in the step (1), and separating by silica gel column chromatography to obtain a solid product compound 3;
(3) Respectively adding dichloromethane, methanol, ammonium chloride and zinc into the compound 3 in the step (2), and carrying out heating reflux reaction to obtain a reaction solution 2;
(4) And (3) respectively washing, extracting, drying, performing column chromatography and spin-drying the reaction liquid 2 in the step (3) to obtain a green solid compound I.
3. The method according to claim 2, wherein in the step (1), the molar ratio of the heptafluoro-borodipyrrole compound 1 to the compound 2 is 1:1-10.
4. The method according to claim 2, wherein the feeding sequence of the step (1) is seven-membered boron dipyrrole compound 1, toluene, compound 2, piperidine and acetic acid; the feeding mole ratio of the compound 1 to the piperidine to the acetic acid is 1:1-10:1-10.
5. The method of claim 2, wherein the heating temperature in step (1) is 100 to 140 ℃ and the heating time is 6 to 12 hours.
6. The use of the fluorescent probe according to claim 1 for detecting hydrochloric acid, trifluoroacetic acid, sulfuric acid and nitric acid in a liquid environment selected from one or more of water, ethanol, acetonitrile, PBS and DMSO.
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| CN111100476A (en) * | 2019-12-05 | 2020-05-05 | 三峡大学 | Synthesis and application of pH fluorescent probe |
| CN113105488A (en) * | 2021-03-17 | 2021-07-13 | 三峡大学 | Synthesis method and application of viscosity-responsive conjugated BOPYIN fluorescent dye |
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| CN111100476A (en) * | 2019-12-05 | 2020-05-05 | 三峡大学 | Synthesis and application of pH fluorescent probe |
| CN113105488A (en) * | 2021-03-17 | 2021-07-13 | 三峡大学 | Synthesis method and application of viscosity-responsive conjugated BOPYIN fluorescent dye |
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