CN109912635A - It is a kind of using BODIPY as benzo-crown ether class compound, the Preparation method and use of fluorogen - Google Patents
It is a kind of using BODIPY as benzo-crown ether class compound, the Preparation method and use of fluorogen Download PDFInfo
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Abstract
The invention discloses a kind of using BODIPY as benzo-crown ether class compound, the Preparation method and use of fluorogen, is related to the detection technique field of the salt in environment, pesticide, food and industrial circle containing potassium.It is with 8- methyl BODIPY and 18- bromo- 2,3,5,6,8,9,11,12,14,15- decahydro benzos [b] [1,4,7,10,13,16] six oxygen rings, 14 carbon tetraene synthesizes 8- [18- methyl -2,3 under the action of catalyst acetic acid palladium, 5,6,8,9,11,12,14,15- decahydro benzo [b] [Isosorbide-5-Nitraes, 7,10,13,16] six oxygen rings, 14 carbon tetraene] BODIPY, which can be used as a kind of detection of fluorescent molecular probe for potassium ion in environment, pesticide, food and industrial circle, also can be used as and diagnoses the illness and the labelled reagent of quality monitoring.
Description
Technical field:
The present invention relates to the invention belongs to spectrofluorimetry technology, a kind of completely new fluorescence point is synthesized by palladium chtalyst
Son, by it, we realize the detection and analysis to potassium ion.
Background technique:
1. fluorescence analysis refers to that the characteristic for generating fluorescence under ultraviolet light using Cucumber and its intensity carry out object
The method of the qualitative and quantitative analysis of matter.G.G. Stokes (G.G.Strokes) discovery fluorescence in 1852, real fluorescence
Spectral measurement then starts from 1960's.
2. sample and known substance are placed under ultraviolet source, root by quantitative fluorescence analysis simultaneously frequently with direct comparison method
Property, color and the intensity to be fluoresced according to them, identifies whether they contain same fluorescent material.Certain is being added in Cucumber
After kind reagent, product can generate fluorescence, and same method identification can also be used.Most common method is to use sepectrophotofluorometer
The fluorescence excitation spectrum and fluorescence emission spectrum of sample are drawn, and is compared with both spectrum of known substance, to reflect
Determine ingredient.Quantitative fluorescence analysis is the standard solution that known fluorescent material is first made into various concentration, uses fluorescence spectrophotometer
Its fluorescence intensity at a certain wavelength of photometer measurement simultaneously draws standard curve, measures examination under conditions of then identical again
The fluorescence intensity of sample is found the content of test substance by standard curve.Since the seventies, fluorescence analysis is in instrument, method and examination
Agent etc. development is very fast, has a wide range of applications in environmental monitoring: carrying out fluorescence analysis by means of organic reagent
Inorganic elements is up to more than 60, and sensitivity for analysis is close with Atomic absorption spectrometry up to micrograms per litre grade, but spectra1 interfer- is few；It is glimmering
Photodetector and liquid chromatograph are combined, and quantitative analysis can be carried out to organic pollutant, as water and waste water are unified in monitoring method
The measurement of polycyclic aromatic hydrocarbon and paper layer fluorescence analysis survey BaP etc..
3. Multifunction fluorescent fluorescent dye BODIPY (4,4- bis- fluoro- 4- boron -3a, 4a- diaza-s- and hexichol), because
Its superior chemistry and photophysics property become one of the basic building block of current organic optoelectronic material, in functional BODIPY
In, having the BODIPY of the pi-conjugated length of extension is the key that class in such compound.By π-extension, can fine-tune
Energy gap and photophysical property between HOMO and LUMO, it will usually which generating compared with parent BODIPY core there is red shift to inhale
Transmit/receive the molecule for penetrating maximum value.They usually can be by between transition metal-catalyzed BODIPY core and aromatic moiety
CC coupling, or the traditional preparation methods by using functionalization pyrroles and benzaldehyde.
Summary of the invention:
One of the objects of the present invention is to provide a kind of new using BODIPY as the benzo-crown ether class compound of fluorogen.
The present invention has the following structure formula using BODIPY as the benzo-crown ether class compound of fluorogen:
The compound molecular weight is 572.29, identifies to obtain above-mentioned molecular structural formula by nucleus magnetic hydrogen spectrum, the present invention has
Fluorescent chromophore BODIPY parent ring, auxiliary substituent roll into a ball benzo-crown ether, can be used as a kind of fluorescent molecular probe, are used for ring
The detection of sylvite in border, medicine, food and health field also can be used as and diagnose the illness and the labelled reagent of quality monitoring.
The second object of the present invention is to providing above-mentioned using BODIPY as the preparation method of the benzo-crown ether class compound of fluorogen.
Its by by the bromo- 2,3,5,6,8,9,11,12,14,15- decahydro benzo [b] of 8- methyl BODIPY and 18- [1,4,
7,10,13,16] six oxygen rings, 14 carbon tetraene synthesized under the action of catalyst acetic acid palladium 8- [methyl -2,3,5,6,8 18-,
14 carbon tetraene of 9,11,12,14,15- decahydro benzo [b] [1,4,7,10,13,16] six oxygen ring] BODIPY is (hereinafter referred to as: 18
It is preced with 6BODIPY), which is described using BODIPY as the benzo-crown ether class compound of fluorogen.
Specifically, being carried out as follows when should be prepared using BODIPY as the benzo-crown ether class compound of fluorogen:
First by the bromo- 2,3,5,6,8,9,11,12,14,15- decahydro benzo [b] of described 8- methyl BODIPY, 18- [1,4,7,
10,13,16] solvent Isosorbide-5-Nitrae dioxane is added in six oxygen rings, 14 carbon tetraene, palladium acetate catalysts is added, with PPh3For
Catalyst ligand, while K is added2CO3Hydrogen bromide absorbent is generated for being catalyzed；Described 8- methyl BODIPY, 18- bromo- 2,3,5,
14 carbon tetraene of 6,8,9,11,12,14,15- decahydro benzo [b] [1,4,7,10,13,16] six oxygen ring, 1,4 dioxane, vinegar
Sour palladium, PPh3And K2CO3Dosage molar ratio be (19~21): (23~25): (1500~2000): (0.9~1.1): (1.9~
2.1): (1.9~2.1) after raw material is stirred to react 12~18 hours under 95~105 DEG C, anhydrous and oxygen-free environment, reaction is mixed
Object object pours into CH2Cl2In to quench the reaction, after being washed with water, then through MgSO4It dries, filters, is then evaporated on revolving instrument, most
Pass through column chromatography [silica afterwards；Heptane/methylene chloride；1:2 (v/v)] purifying obtain it is described using BODIPY as the benzene of fluorogen
And crown ether compound.
The present invention is by the scheme of C (sp3)-H arylation of palladium chtalyst, with 8- methyl BODIPY and 18- bromo- 2,3,5,6,
14 carbon tetraene of 8,9,11,12,14,15- decahydro benzo [b] [1,4,7,10,13,16] six oxygen ring (4- bromobenzene and 18 hats 6) is made
For substrate, reaction generates target product 18 and is preced with 6BODIPY.
The above-mentioned bromo- 2,3,5,6,8,9,11,12,14,15- decahydro benzo [b] of 8- methyl BODIPY and 18- [1,4,7,10,
13,16] molar ratio of six oxygen rings, 14 carbon tetraene is 1 ︰ 1.2.It is using the purpose of the molar ratio: 18- bromo- 2,3,5,6,
In 14 carbon tetraene of 8,9,11,12,14,15- decahydro benzo [b] [1,4,7,10,13,16] six oxygen ring in a small amount of molecule on phenyl ring
Bromine can be captured by Pd, to generate by-product, thus the 18- bromo- 2 for needing mole slightly more, 3,5,6,8,9,11,12,14,
14 carbon tetraene of 15- decahydro benzo [b] [1,4,7,10,13,16] six oxygen ring.
What the present invention obtained is a kind of completely new compound, and rationally, simply, low in raw material price meets processing step
The material stability of the theory of Green Chemistry and atom economy, synthesis is good, and compared with prior art, the present invention has following excellent
Point:
1, because the hydrogen of the methyl on 8 has acidity, pass through the C (sp of palladium chtalyst3) (the intersection dehydrogenation coupling of-H arylation
Reaction) scheme synthesis, reaction can by bromo- 2,3,5,6,8,9,11,12,14,15- decahydro benzo [b] of 18- [Isosorbide-5-Nitrae, 7,10,
13,16] six oxygen rings, 14 carbon tetraene is mounted directly to the meso methyl of BODIPY, generate aromatic fractions and BODIPY core it
Between p- be conjugated the substance that is interrupted by methylene linker.
2, substrate is dissolved in Isosorbide-5-Nitrae dioxane, before palladium acetate is added, dissolved with 8- methyl BODIPY, 18- bromo- 2,3,
1,4 dioxane of 14 carbon tetraene of 5,6,8,9,11,12,14,15- decahydro benzo [b] [1,4,7,10,13,16] six oxygen ring
10~15min is purged with argon gas.Guarantee that reaction carries out in the environment of anhydrous and oxygen-free, further ensures that the catalysis of palladium acetate is living
Property.
3, the new compound of one kind provided by the invention, it is with a benzo 18- methyl -2,3, and 5,6,8,9,11,12,
14 carbon tetraene of 14,15- decahydro benzo [b] [1,4,7,10,13,16] six oxygen ring is substituent group instead of 8- methyl BODPIPY
In acidic hydrogen on 8 methyl, although two such aromatic rings has obstructed conjugated structure by a methylene, 18- methyl -2,3,
14 carbon tetraene group of 5,6,8,9,11,12,14,15- decahydro benzo [b] [1,4,7,10,13,16] six oxygen ring still connects very much
Nearly BODIPY core allows effective electronics/energy transfer between substituent group and BODIPY, using 18 hats 6 as reactive group,
It can be used as a kind of detection of fluorescent molecular probe for K+ in environment, medicine, food and health field, also can be used as quality monitoring
Labelled reagent.
4, in direct C (sp3)-H arylation and direct BODIPY C (sp2) in-H arylation, ligand rises in coupling efficiency
Key effect selects PPh in this synthesis3As ligand, acceptable yield is obtained, yield is about 35-40%.
Third object of the present invention is to provide be preced with using BODPIPY as the benzo-crown ether class compound of fluorogen, i.e., 18
The purposes of 6BODIPY.Its purposes is: the benzo-crown ether class compound that BODPIPY is fluorogen is used as fluorescent molecular probe
In detection K+, K+By being generated after any one hydrolysis in the inorganic salts of potassium.
Concrete application method is: preparing more parts of potassium nitrate and described using BODIPY as the benzo-crown ether class compound of fluorogen
Standard solution, when preparation, keep described constant as the concentration of the benzo-crown ether class compound of fluorogen using BODIPY, pass through drop
Surely potassium nitrate solution is gradually added into obtain the mixed liquor of different proportion, by K in potassium nitrate solution+Molar concentration be converted into K+
Relative to described using BODIPY as the molar equivalent of the benzo-crown ether class compound of fluorogen, using Fluorescence Spectrometer as detector
Device, using launch wavelength as abscissa, with above-mentioned K+The corresponding fluorescence intensity of molar equivalent be ordinate, make fluorescence song
Line；Its fluorescence song is observed after addition is described using BODIPY as the solution of the benzo-crown ether class compound of fluorogen in solution to be detected
The variation of line, being compared by it with fluorescence curve may be implemented K in solution+Quantitative detection.
Detailed description of the invention:
Fig. 1 is the nucleus magnetic hydrogen spectrum figure for the 18 hat 6BODIPY that the present invention synthesizes.
Fig. 2 is the nuclear-magnetism carbon spectrogram for the 18 hat 6BODIPY that the present invention synthesizes.
Fig. 3 passes through K2CO3(exciting in 488nm) fluorescence titration compound 18 is preced with 6BODIPY figure.
Fig. 4 passes through K2CO3Fluorescence intensity becomes at the 510nm that (exciting in 488nm) fluorescence titration compound 18 is preced with 6BODIPY
Change tendency chart.
Specific embodiment
Embodiment 1
One, the synthesis step of 18 hat 6BODIPY:
1, addition 8- methyl BODIPY (0.2mmol, 54mg) and 18- bromo- 2 in 15ml air-tight bottle, 3,5,6,8,9,11,
12,14,15- decahydro benzo [b] [Isosorbide-5-Nitrae, 7,10,13,16] six oxygen ring, 14 carbon tetraene (0.24mmol, 94mg), by air-tight bottle
It is fixed on thermostatic mixer, the Isosorbide-5-Nitrae oxepane (about 20mmol, 1730mg) of 2ml is added, then put a sizeable magnetic
For power stirrer in bottle, the pipe of argon bottle connects a syringe needle, and syringe needle is submerged, and opening argon gas valve, will be molten to blast argon gas
The oxygen and water dissolved in liquid is discharged, and stops logical argon gas after 15min, removes syringe needle, connect argon bottle from the interface of side, be passed through
Argon gas purges 15min, and Pd (OAc) then is added2(0.01mmol, the molar ratio with raw material BODIPY are 1:20), PPh3
(0.02mmol) and K2CO3(0.2mmol).Then, by mixture at 100 DEG C heating stirring (300r) 15 hours.
2, next, crude mixture is poured into CH2Cl2In (80-120ml) to quench the reaction, then with water (100ml) it washs
Three times, through MgSO4It dries, filters, is evaporated to dryness on revolving instrument.Pass through column chromatography [silica；Heptane/methylene chloride；1:
2 (v/v)] it obtains, be orange solids (41.7mg, 37%).
3, the 18 hat 6BODIPY that verifying obtains have the method for following molecular structural formula:
As shown in Figure 1, the product that above step 1,2 synthesizes is identified to obtain following molecular structural formulas by nucleus magnetic hydrogen spectrum:
Two, it applies: measuring K using 18 hat 6BODIPY as fluorescent labeling reagent+Presence:
1, instrument and condition:
The steady state emission spectrum of correction is recorded on SPEX Fluorolog, fluorescence detector excitation wavelength is 488nm, is made
All fluorescent emission measurements are carried out with the freshly prepd sample in 1cm quartz cell, record letter of multiple fluorescence spectrums as concentration
Number is used only in the dilution that absorbance under excitation wavelength is lower than 0.1 to measure the relative fluorescence quantum yield (Ф) in solution
Solution.It is measured under right angle (L-) arrangement and " magic angle " polarization conditions using the cuvette of 10mm optical path length.Rhodamine
6G is used as fluorescence quantum yield reference in ethanol (Ф r=0.88 is excited in 488nm).
2, the excitation and launch wavelength of 18 hat 6BODIPY are determined:
18 hat 6BODIPY are configured to the standard solution that concentration is 5 μm of ol/L with ethyl alcohol.
With SPEX Fluorolog fluorescent spectrophotometer assay, its excitation wavelength E is measuredx=488nm, launch wavelength Em
=510nm.
5, K in solution+The existing detection of ion:
Use K2CO3Aqueous solution fluorescence titration 18 be preced with 6BODIPY ethyl alcohol (1 μm of ol/L) solution be tested.Configuration
The K of 18 hat 6BODIPY the ethanol solution 10ml, 0.5mmol/L of 1mmol/L2CO3Aqueous solution 10ml takes 3ml ethyl alcohol in four-way ratio
In color ware, 3ml 18 is added and is preced with 6BODIPY standard solution, tests its fluorescence emission curves.Then 3 μ L k are added every time2CO3In
In four-way cuvette, its fluorescence emission curves is tested respectively, and fluorescence emission curves are recorded in Fig. 3.It is micro- in ethanol solution
Amount addition K2CO3Aqueous solution can observe that fluorescence intensity slightly enhances, as K in ethyl alcohol at 510nm+Concentration reach 10 μ
When mol/L (about 10 equivalents are preced with 6BODIPY in 18), the fluorescence intensity enhancing ratio at 510nm reaches 1.3.
The fluorescence intensity change that its 510nm goes out sees table one, and variation tendency is found in Fig. 4.
Table one
Fig. 4 is K+The standard curve of concentration is compared after solution to be detected is handled by the above method by standard curve
It can be with the concentration of the potassium ion in quantitative detection solution.
Three, feature of the present invention:
1, the present invention has synthesized a kind of new BODIPY fluorescent molecule group for the first time, with the pyrroles's de novo formation method used in the past
It compares, does not need from the beginning to synthesize step by step, it can be with 8- methyl BODIPY and bromo aromatic compound one-step synthesis, synthesis step
Simply, operation is simple, and yield is considerable.
2, meeting the theory of atom economy and Green Chemistry, the synthesis of 18 hat 6BODIPY is simple, it has good stability, raw material
It is cheap, it is nontoxic.
3, induction force of the molecule to K ion is tested using fluorescence titrimetric method, it is easy to operate, without adding other
Color developing agent, reference solution, fluorescence enhancement naked eyes it is visible.
Embodiment 2
The preparation method of 18 hat 6BODIPY, carries out as follows:
Raw material dosage:
8- methyl BODIPY dosage is 19mmol；
14 carbon of [1,4,7,10,13,16] six oxygen ring of the bromo- 2,3,5,6,8,9,11,12,14,15- decahydro benzo [b] of 18-
Tetraene dosage is 23mmol；
1,4 dioxane dosages are 1500mmol；
Palladium acetate dosage is 1.1mmol；
PPh3Dosage is 1.9mmol；
K2CO3Dosage be 2.1mol；
First by the bromo- 2,3,5,6,8,9,11,12,14,15- decahydro benzo [b] of described 8- methyl BODIPY, 18- [1,4,7,
10,13,16] six oxygen rings, 14 carbon tetraene is added in solvent Isosorbide-5-Nitrae dioxane, palladium acetate is added, with PPh3For ligand, simultaneously
K is added2CO3；
After raw material is stirred to react 18 hours under 95 DEG C, anhydrous and oxygen-free environment, crude mixture is poured into CH2Cl2In, use water
After washing 2 times, then through MgSO4It dries, filters, is then evaporated on revolving instrument, finally by column chromatography [silica；Heptane/
Methylene chloride；1:2 (v/v)] purifying obtain 8- [18- methyl -2,3,5,6,8,9,11,12,14,15- decahydro benzo [b] [1,4,
7,10,13,16] six oxygen rings, 14 carbon tetraene] BODIPY, as 18 hat 6BODIPY.
Embodiment 3
Raw material dosage:
8- methyl BODIPY dosage is 21mmol；
14 carbon of [1,4,7,10,13,16] six oxygen ring of the bromo- 2,3,5,6,8,9,11,12,14,15- decahydro benzo [b] of 18-
Tetraene dosage is 25mmol；
1,4 dioxane dosages are 1800mmol；
Palladium acetate dosage is 0.9mmol；
PPh3Dosage is 2.1mmol；
K2CO3Dosage be 1.9mmol；
First by the bromo- 2,3,5,6,8,9,11,12,14,15- decahydro benzo [b] of described 8- methyl BODIPY, 18- [1,4,7,
10,13,16] six oxygen rings, 14 carbon tetraene is added in solvent Isosorbide-5-Nitrae dioxane, palladium acetate is added, with PPh3For ligand, simultaneously
K is added2CO3；
After raw material is stirred to react 12 hours under 105 DEG C, anhydrous and oxygen-free environment, crude mixture is poured into CH2Cl2In, use water
After washing 4 times, then through MgSO4It dries, filters, is then evaporated on revolving instrument, finally by column chromatography [silica；Heptane/
Methylene chloride；1:2 (v/v)] purifying obtain 8- [18- methyl -2,3,5,6,8,9,11,12,14,15- decahydro benzo [b] [1,4,
7,10,13,16] six oxygen rings, 14 carbon tetraene] BODIPY, as 18 hat 6BODIPY.
Embodiment 4
Raw material dosage:
8- methyl BODIPY dosage is 20mmol；
14 carbon of [1,4,7,10,13,16] six oxygen ring of the bromo- 2,3,5,6,8,9,11,12,14,15- decahydro benzo [b] of 18-
Tetraene dosage is 24mmol；
1,4 dioxane dosages are 2000mmol；
Palladium acetate dosage is 0.9mmol；
PPh3Dosage is 2.0mmol；
K2CO3Dosage be 1.9mmol；
First by the bromo- 2,3,5,6,8,9,11,12,14,15- decahydro benzo [b] of described 8- methyl BODIPY, 18- [1,4,7,
10,13,16] six oxygen rings, 14 carbon tetraene is added in solvent Isosorbide-5-Nitrae dioxane, palladium acetate is added, with PPh3For ligand, simultaneously
K is added2CO3；
After raw material is stirred to react 12~18 hours under 95~105 DEG C, anhydrous and oxygen-free environment, crude mixture is poured into
CH2Cl2In, after being washed with water, then through MgSO4It dries, filters, is then evaporated on revolving instrument, finally by column chromatography [dioxy
SiClx；Heptane/methylene chloride；1:2 (v/v)] purifying obtain 8- [18- methyl -2,3,5,6,8,9,11,12,14,15- decahydro benzene
And 14 carbon tetraene of [b] [Isosorbide-5-Nitrae, 7,10,13,16] six oxygen ring] BODIPY, as 18 hat 6BODIPY.
The present invention is not limited to the above embodiments, on the basis of technical solution disclosed by the invention, the skill of this field
For art personnel according to disclosed technology contents, one can be made to some of which technical characteristic by not needing creative labor
A little replacements and deformation, these replacements and deformation are within the scope of the invention.
Claims (6)
1. a kind of using BODIPY as the benzo-crown ether class compound of fluorogen, it is characterised in that the structural formula of the compound are as follows:
2. one kind is as described in claim 1 using BODIPY as the preparation method of the benzo-crown ether class compound of fluorogen, special
Sign be by the bromo- 2,3,5,6,8,9,11,12,14,15- decahydro benzo [b] of 8- methyl BODIPY and 18- [1,4,7,10,13,
16] six oxygen rings, 14 carbon tetraene synthesized under the action of catalyst acetic acid palladium 8- [methyl -2,3,5,6,8,9,11,12 18-,
14,15- decahydro benzo [b] [Isosorbide-5-Nitrae, 7,10,13,16] six oxygen ring, 14 carbon tetraene] BODIPY, the compound be it is described with
BODIPY is the benzo-crown ether class compound of fluorogen.
3. as claimed in claim 2 using BODIPY as the preparation method of the benzo-crown ether class compound of fluorogen, feature exists
It is carried out in as follows:
First by the bromo- 2,3,5,6,8,9,11,12,14,15- decahydro benzo [b] of described 8- methyl BODIPY, 18- [1,4,7,10,
13,16] solvent Isosorbide-5-Nitrae dioxane is added in six oxygen rings, 14 carbon tetraene, palladium acetate catalysts is added, with PPh3For catalysis
Agent ligand, while K is added2CO3Hydrogen bromide absorbent is generated for being catalyzed；Described 8- methyl BODIPY, 18- bromo- 2,3,5,6,8,
14 carbon tetraene of 9,11,12,14,15- decahydro benzo [b] [1,4,7,10,13,16] six oxygen ring, 1,4 dioxane, palladium acetate,
PPh3And K2CO3Dosage molar ratio be (19~21): (23~25): (1500~2000): (0.9~1.1): (1.9~2.1):
(1.9~2.1), after raw material is stirred to react 12~18 hours under 95~105 DEG C, anhydrous and oxygen-free environment, by reaction mixture object
Pour into CH2Cl2In to quench the reaction, after being washed with water, then through MgSO4It dries, filters, is then evaporated on revolving instrument, finally leads to
Cross column chromatography [silica；Heptane/methylene chloride；1:2 (v/v)] purifying obtains described being preced with by the benzo of fluorogen of BODIPY
Ether compound.
4. as claimed in claim 2 using BODIPY as the preparation method of the benzo-crown ether class compound of fluorogen, feature exists
In before palladium acetate is added, dissolved with bromo- 2,3,5,6,8,9,11,12,14,15- decahydro benzo [b] of 8- methyl BODIPY, 18-
1,4 dioxane of 14 carbon tetraene of [1,4,7,10,13,16] six oxygen ring purge 10~15min with argon gas.
5. special using BODIPY as the purposes of the benzo-crown ether class compound of fluorogen as described in claim 1-4 any one
Sign is to be used for the benzo-crown ether class compound of BODIPY fluorogen to detect K as fluorescent molecular probe+。
6. according to claim 5 using BODIPY as the purposes of the benzo-crown ether class compound of fluorogen, it is characterised in that by as follows
Step carries out: preparing more parts of potassium nitrate and described using BODIPY as the standard solution of the benzo-crown ether class compound of fluorogen, matches
When processed, keep described constant as the concentration of the benzo-crown ether class compound of fluorogen using BODIPY, nitre is gradually added by titration
Sour potassium solution is to obtain the mixed liquor of different proportion, by K in potassium nitrate solution+Molar concentration be converted into K+Relative to it is described with
BODIPY is the molar equivalent of the benzo-crown ether class compound of fluorogen, using Fluorescence Spectrometer as detecting instrument, with launch wavelength
For abscissa, with above-mentioned K+The corresponding fluorescence intensity of molar equivalent be ordinate, make fluorescence curve；In solution to be detected
Be added it is described using BODIPY as the solution of the benzo-crown ether class compound of fluorogen after observe the variation of its fluorescence curve, pass through it
It is compared with fluorescence curve and K in solution may be implemented+Quantitative detection.
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| BLAKEMORE, JAMES D. ET AL: "Synthesis and study of crown ether-appended boron dipyrrin chemosensors for cation detection", 《TETRAHEDRON LETTERS》 * |
| CHONG, HUI ET AL: "Acid-Sensitive BODIPY Dyes: Synthesis through Pd-Catalyzed Direct C(sp3)-H Arylation and Photophysics", 《CHEMISTRY-A EUROPEAN JOURNAL》 * |
| FRANCIS D’SOUZA ET AL: "Ultrafast excitation transfer and charge stabilization in a newly assembled photosynthetic antenna-reaction center mimic composed of boron dipyrrin, zinc porphyrin and fullerene", 《PHYS. CHEM. CHEM. PHYS.》 * |
| HYUN JUNG KIM ET AL: "BODIPY Appended Crown Ethers: Selective Fluorescence Changes for Hg2+ Binding", 《BULL. KOREAN CHEM. SOC.》 * |
| SHUAI SHAO ET AL: "UltrafastPhotoinducedChargeSeparationin Wide-Band-CapturingSelf-AssembledSupramolecularBis(donor styryl)BODIPY–FullereneConjugates", 《CHEM.EUR.J.》 * |
| 尹振东: "用于荧光探针的氟硼二吡咯衍生物的设计_合成与光物理性质研究", 《吉林大学博士学位论文》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110407675A (en) * | 2019-08-10 | 2019-11-05 | 常州大学 | A kind of preparation of anthryl diethylene glycol monomethyl ether and its identification to potassium ion |
| CN110407675B (en) * | 2019-08-10 | 2022-09-02 | 常州大学 | Preparation of anthracenyl diethylene glycol monomethyl ether and identification of potassium ions by anthracenyl diethylene glycol monomethyl ether |
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