CN109030433A - The preparation and its application in detection hydrogen peroxide and glucose of porphyrin compound fluorescent molecule - Google Patents
The preparation and its application in detection hydrogen peroxide and glucose of porphyrin compound fluorescent molecule Download PDFInfo
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- 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
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/1018—Heterocyclic compounds
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- 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
- C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N2021/6432—Quenching
Abstract
The present invention provides a kind of preparation of porphyrin compound fluorescent molecule and its applications in detection hydrogen peroxide and glucose, and the preparation method: pyrroles is dissolved in propionic acid, obtains dropping liquid；Propionic acid solution oil bath heating to slightly boiled, addition benzaldehyde, dropwise addition dropping liquid reflux is cooled to room temperature, stands；It filters, washs, drying obtains sample；Silica gel column chromatography purifying, rotates, and drying obtains TPP；TPP is dissolved in chloroform, and the concentrated sulfuric acid, agitating and heating, constant temperature reflux is added dropwise, green clear solution is obtained, room temperature is cooled to, ice water is immersed, obtains purple solution, filtering, is spin-dried for, filtrate is filtered with methanol, vacuum drying, obtains crude product, is dissolved in hot methanol, propyl alcohol is added in stirring, until precipitating, filters, propyl alcohol is added in the filtrate collected under stirring conditions again, until precipitating, porphyrin compound fluorescent molecule is made.Fluorescent molecule made from the preparation method is relatively stable, is applied to hydrogen peroxide and glucose detection, is greatly improved the sensitivity of detection.
Description
Technical field
The invention belongs to chemosynthesis technical fields, are related to a kind of preparation method of porphyrin compound fluorescent molecule, are based on
Synthesis green and the higher porphyrins tetrasulfonic acid base phenyl porphyrin (TPPS of yield4), and utilize its stronger fluorescence
Property this feature, construct a kind of sensitive " Turn-off " the type fluorescent optical sensor of comparison to detect hydrogen peroxide and glucose.
Background technique
In recent years, easy to operate, cheap, detection limits low, with higher sensitivity fluorescent technique and is widely used in
The detection of each substance, with the development of science and technology, occurring utilizing institute between fluorescent material molecule and solvent or solute molecule
The method for causing fluorescence to decline or disappear occurred, i.e. fluorescent quenching " Turn-off ".Fluorescent quenching process is actually
The life span of light emitting molecule excitation state is vied each other and shortened with luminescence process, mainly applies following principle: 1) energy transfer
Mechanism；2) charge transfer mechanism.It, can be effective under ultraviolet or visible light action since Porphyrin Molecule has certain photo-sensitive characteristic
Discharge singlet oxygen, thus Porphyrin Molecule be widely used in fluorescence detection, therefore select the excellent molecule of fluorescence property and
Construct the thing that novel fluorescent optical sensor has become very urgent.
Summary of the invention
The object of the present invention is to provide the high porphyrins (TPPS of a kind of green non-pollution, yield4) fluorescent molecule
Preparation method.
It is a further object to provide the fluorescent molecules that prepare in aforementioned manners of one kind in detection hydrogen peroxide and
Application in glucose.
To achieve the above object, the technical scheme adopted by the invention is that: a kind of preparation of porphyrin compound fluorescent molecule
Method, which is characterized in that the preparation method specifically sequentially includes the following steps:
1) 8mL pyrroles is dissolved in 35mL propionic acid, obtains dropping liquid；
2) 250mL propionic acid solution oil bath heating is added into 11mL benzaldehyde, a dropping step 1 to slightly boiled) made from dropping liquid,
Flow back 1h, stops being added dropwise, is cooled to room temperature, stands 12h at a temperature of 4 DEG C；Filter, washed with dehydrated alcohol it is colourless to solution, so
It is washed again with 200mL hot water afterwards, dries, obtain sample；Purified with silica gel column chromatography, rotated, drying is made 5,10,15,20- tetra-
Phenyl porphyrin；
3) made from step 25,10,15,20- tetraphenylporphyrins are dissolved in chloroform, the dropwise addition 10mL concentrated sulfuric acid, under stirring condition
95 DEG C are heated to, constant temperature reflux 4h obtains green clear solution, after being cooled to room temperature, immerses in 50mL ice water, it is molten to obtain purple
Liquid, filtering, remove sodium sulfate crystal, be spin-dried for, after filtrate is filtered with methanol, 80 DEG C at a temperature of be dried in vacuo 8h, obtain and slightly produce
The crude product is dissolved in methanol, propyl alcohol is added under conditions of stirring by product, until precipitate, filters, and obtains purple product, then
Propyl alcohol is added under conditions of stirring in the filtrate collected, until precipitating, repeats to add propyl alcohol agitation and filtration 2~3 in filtrate
It is secondary, porphyrin compound fluorescent molecule is made.
Another technical solution of the present invention is: a kind of preparation method with above-mentioned porphyrin compound fluorescent molecule
Application of the porphyrin compound fluorescent molecule obtained in detection hydrogen peroxide and glucose.
Preparation method of the present invention has the advantages that
1) yield is high, green, and method than before has certain difference and improves, in conjunction with fluorescence probe after formed
Detection probe is ideal in fluorescence detection.
2) easy to operate, it is cheap, reduce its testing cost.
3) fluorescent molecule made from is relatively stable, and external world's influence is smaller, and fluorescence is more stable, and porphyrin compound is in the solution
With strong fluorescence, its table is remembered into fluorescence probe, is applied to hydrogen peroxide and glucose detection, its detection can be greatly improved
Sensitivity.
Detailed description of the invention
Fig. 1 is the hydrogen nuclear magnetic resonance spectrogram of fluorescent molecule made from preparation method of the present invention.
Fig. 2 is the infrared spectrum of fluorescent molecule made from preparation method of the present invention.
Fig. 3 is the fluorescent emission figure of fluorescent molecule made from preparation method of the present invention.
Fig. 4 is TPPS4-Fe2+Detect H2O2Fluorescent quenching figure.
Fig. 5 is TPPS4-Fe3+Fluorescent quenching figure.
Specific embodiment
Above scheme is further detailed below in conjunction with specific embodiment, these specific embodiments and be not limited to
It limits the scope of the invention.The implementation condition being not specified is the generally conventional condition of experiment, if temperature is ambient temperature.
The present invention provides a kind of preparation methods of porphyrins fluorescent molecule, specifically sequentially include the following steps:
1) 8mL pyrroles is dissolved in 35mL propionic acid, obtains dropping liquid；
2) 250mL propionic acid solution is added in three neck round bottom, oil bath heating adds 11mL benzaldehyde, by step to slightly boiled
1) dropping liquid made from is slowly added drop-wise in reaction flask the 1h that flows back, and stops being added dropwise, be cooled to room temperature, and is put into (4 DEG C) of refrigerator overnight
(12h)；It filters, is washed with dehydrated alcohol colourless to solution, then wash 2~3 with 200mL temperature again for 50~65 DEG C of hot water
It is secondary, after drying, obtain purple sample；To be purified with silica gel column chromatography, methylene chloride and petroleum ether (3 ︰ 1 of volume ratio) they are eluant, eluent,
5,10,15,20- tetraphenylporphyrins (TPP) (0.3mM) are made in revolving, drying；
3) in the three neck round bottom of 100mL, TPP made from step 2 is dissolved in chloroform, the 10mL concentrated sulfuric acid is slowly added dropwise,
95 DEG C are heated under stirring condition, constant temperature reflux 4h obtains green clear solution, careful to immerse 50mL ice after being cooled to room temperature
In water (0 DEG C), purple solution is obtained, is filtered, sodium sulfate crystal is removed, is spin-dried for, after filtrate continues filtering with methanol, at 80 DEG C
At a temperature of be dried in vacuo 8h, obtain crude product, which, which is dissolved in temperature, is in 30~55 DEG C of methanol, under conditions of stirring plus
Enter propyl alcohol, until precipitating, filter, obtain purple product, then propyl alcohol is added under stirring conditions in the filtrate collected, until going out
It now precipitates, repeats to add propyl alcohol agitation and filtration 2~3 times in filtrate, obtain sterling tetrasulfonic acid base phenyl porphyrin (TPPS4)
78.7mg, yield 50% or so, the sterling tetrasulfonic acid base phenyl porphyrin are porphyrin compound fluorescent molecule obtained.
Reaction equation in the preparation process of porphyrins fluorescent molecule are as follows:
Since porphyrin material has unique photoelectric characteristic, preparation method of the present invention is with existing tetrasulfonic acid base phenyl
Porphyrin (TPPS4) preparation method based on, improved, synthesized green and the TPPS that is significantly improved of yield4。
The present invention also provides a kind of, and the tetrasulfonic acid base phenyl porphyrin made from above-mentioned preparation method is detecting hydrogen peroxide
With the application in glucose, that is, utilize the TPPS of function admirable obtained above4Construct a kind of novel, sensitive " Turn-
Off " type fluorescent optical sensor detects hydrogen peroxide and glucose.Specifically:
When for detecting hydrogen peroxide: (0.1M) TPPS by made from4Aqueous solution, 500 μ L ultrapure waters are added, then are separately added into
30μL Fe2+Solution (2.6mM) and 500 μ L(0.1M) Tris-HCl buffer solution (pH=7.4), in the excitation wavelength of 515nm
Lower excitation, wave-length coverage are 600~800nm, due to energy loss being accompanied by, so launch wavelength during electron excitation
It generally to be grown compared with excitation wavelength, slit width is all 10nm.
Embodiment 1
8mL pyrroles is dissolved in 35mL propionic acid, dropping liquid is obtained；250mL propionic acid solution, oil bath heating are added in three neck round bottom
It is extremely slightly boiled, 11mL benzaldehyde is added, dropping liquid obtained is slowly added drop-wise in reaction flask the 1h that flows back, stops being added dropwise, it is cooling
To room temperature, it is put into refrigerator 12h；Filter, it is colourless with first value solution is washed with dehydrated alcohol, then again with 200ml hot water (50 DEG C-
65 DEG C) washing 2~3 times, after drying, obtain purple sample；Purified with silica gel column chromatography, methylene chloride and petroleum ether are eluant, eluent
(volume ratio is 3 ︰ 1), rotates, and 5,10,15,20- tetraphenylporphyrins (TPP) (0.3mM) are made in drying；In the three necks circle of 100mL
In the flask of bottom, TPP obtained is dissolved in chloroform, the concentrated sulfuric acid of 10mL is added dropwise, 95 DEG C, constant temperature reflux 4h are heated under stirring,
Green clear solution is obtained, after being cooled to room temperature, by its careful immersion ice water (0 DEG C), purple solution is obtained, filters, remove
Sodium sulfate crystal is spin-dried for, and after filtrate continues filtering with methanol, in 80 DEG C of vacuum drying 8h, crude product is dissolved in hot methanol, adds third
Alcohol, stirring, is precipitated, and purple product occurs in filtering, is repeated to add the operation such as propyl alcohol agitation and filtration 2~3 times, is obtained four sulphur of sterling
Acidic group phenyl porphyrin (TPPS4) 78.7mg, yield 50% or so.
Accurately weigh TPPS made from 0.20mg embodiment 14, it is dried in vacuo and is placed in nuclear magnetic tube, DMSO-d is added6It is molten
Agent carries out nuclear magnetic resonance hydrogen spectruming determining, as shown in Figure 1, testing the chemical displacement value of each compound measured as can be seen from Figure 1
It is as follows:1H NMR (400MHz, DMSO-d6) δ, ppm:8.85 (s, 8H), 8.17 (d, 8H, J=4.0Hz), 8.06
(d, 8H, J=8.0Hz), -2.94(s, 2H).The TPPS4Infrared spectrum, see Fig. 2, as can be seen from Figure 2 phenyl ring and porphin
The stretching vibration absworption peak 1445cm of C=C on quinoline ring−1Left and right；C-H stretching vibration absworption peak on aromatic ring is in 2580cm-1~
2940cm-1Left and right；Sulfonic characteristic absorption peak is respectively 1179cm-1、 1129cm-1And 638cm-1；1650 cm-1Left and right
For the stretching vibration of C-O, the stretching vibration absworption peak 1667cm of N=C on porphyrin ring and on phenyl ring-1 And 1609cm-1 Left and right.It should
TPPS4Fluorescent emission figure, irradiated as shown in figure 3, can be seen that from Fig. 3 fluorescence emission spectrum when with the excitation wavelength of 515nm
TPPS4When solution, it will appear two obvious fluorescence emission peaks in 645nm and 700nm.
The TPPS made from embodiment 14Detect hydrogen peroxide (H2O2): with TPPS obtained4Compound concentration is 0.1M's
TPPS4Aqueous solution；Pipetting 200 μ L should (0.1M) TPPS4Aqueous solution is added 500 μ L ultrapure waters, then is separately added into 30 μ L Fe2+It is molten
Liquid (2.6mM) and 500 μ L(0.1M) Tris-HCl buffer solution, obtain TPPS4-Fe2+Probe stock solution, in the excitation of 515nm
It is excited under wavelength, obtains fluorescent emission figure shown in Fig. 3, it is seen that TPPS4Excitation wavelength be 515nm, wave-length coverage be 600~
800nm, slit width are 10nm.
To the TPPS of preparation4-Fe2+The H of various concentration is added in probe stock solution2O2Solution observes fluorescence with H2O2It is dense
The increase of degree and the phenomenon that gradually quench, when being added to a certain extent, fluorescence is no longer changed, and sees Fig. 4, can be with from Fig. 4
Find out TPPS4-Fe2+The fluorescence intensity of system is with various concentration H2O2Solution concentration situation of change, with H2O2Solution is dense
Degree is continuously increased, TPPS4-Fe2+The continuous reduction of the fluorescence intensity of system, when being added to a certain extent, fluorescence is no longer sent out
Changing shows TPPS this moment4Fluorescent quenching degree has reached minimum.
The TPPS made from preparation method of the present invention4Detect H2O2, minimum detection limit (LOD) is 1.24nM.
Due to the ferrous ion (Fe in solution2+) ferric ion (Fe can be become by hydrogen peroxide oxidation3+), reaction
Formula are as follows: 2Fe2+(aq)+H2O2+2H+(aq)→2Fe3+(aq)+2H2O(l)；And ferric ion (Fe3+) meeting and TPPS4Formation is matched
Object, further occurrence charge transfer process are closed, the fluorescent quenching figure of principle is shown in Fig. 5.The present invention is made using this process
TPPS4Fluorescence reduce, be finally reached the detection to hydrogen peroxide.
For further expansion TPPS4-Fe2+The probe is used to detect some blood by the application range of probe, the present invention
Glucose in liquid or cell.Specific detection method are as follows: to above-mentioned TPPS4-Fe2+It is added in probe stock solution a certain amount of
Then the glucose of various concentration is added in glucose oxidase, observe the variation that fluorescence intensity occurs, can quench fluorescence.
Minimum detection limit (LOD) to the glucose in blood or cell is 0.38nM.
Utilize TPPS4-Fe2+Fluorescence probe can be widely applied to blood, in urine and cell glucose detection.
The present invention not only solves the detection to hydrogen peroxide, also expands based on the above principles to common general substance
The detection of glucose, detection method is not only easy to operate but also low in cost, sensitivity is relatively strong, time-consuming less, therefore can be pushed away
Chong Liyong.
Claims (7)
1. a kind of preparation method of porphyrin compound fluorescent molecule, which is characterized in that the preparation method specifically according to the following steps into
Row:
1) 8mL pyrroles is dissolved in 35mL propionic acid, obtains dropping liquid；
2) 250mL propionic acid solution oil bath heating is added into 11mL benzaldehyde, a dropping step 1 to slightly boiled) made from dropping liquid,
Flow back 1h, stops being added dropwise, is cooled to room temperature, stands 12h at a temperature of 4 DEG C；Filter, washed with dehydrated alcohol it is colourless to solution, so
It is washed again with 200mL hot water afterwards, dries, obtain sample；Purified with silica gel column chromatography, rotated, drying is made 5,10,15,20- tetra-
Phenyl porphyrin；
3) made from step 25,10,15,20- tetraphenylporphyrins are dissolved in chloroform, the dropwise addition 10mL concentrated sulfuric acid, under stirring condition
95 DEG C are heated to, constant temperature reflux 4h obtains green clear solution, after being cooled to room temperature, immerses in 50mL ice water, it is molten to obtain purple
Liquid, filtering, remove sodium sulfate crystal, be spin-dried for, after filtrate is filtered with methanol, 80 DEG C at a temperature of be dried in vacuo 8h, obtain and slightly produce
The crude product is dissolved in methanol, propyl alcohol is added under conditions of stirring by product, until precipitate, filters, and obtains purple product, then
Propyl alcohol is added under conditions of stirring in the filtrate collected, until precipitating, repeats to add propyl alcohol agitation and filtration 2~3 in filtrate
It is secondary, porphyrin compound fluorescent molecule is made.
2. the preparation method of porphyrin compound fluorescent molecule according to claim 1, which is characterized in that the step 2
In, when being purified with silica gel column chromatography, using eluant, eluent, which is made of methylene chloride and petroleum ether, methylene chloride and stone
The volume ratio of oily ether is 3 ︰ 1.
3. the preparation method of porphyrin compound fluorescent molecule according to claim 1, which is characterized in that the step 2
In, filter, with dehydrated alcohol wash to solution it is colourless after, then washed for 50~65 DEG C of hot water with 200mL temperature.
4. the preparation method of porphyrin compound fluorescent molecule according to claim 1, which is characterized in that the step 3)
In, crude product is dissolved in the methanol that temperature is 30~55 DEG C.
5. porphyrin compound fluorescence made from a kind of preparation method with porphyrin compound fluorescent molecule described in claim 1 point
Application of the son in detection hydrogen peroxide and glucose.
6. application of the porphyrin compound fluorescent molecule according to claim 5 in detection hydrogen peroxide and glucose,
It is characterized in that, when for detecting hydrogen peroxide: by the aqueous solution of porphyrin compound fluorescent molecule obtained, it is ultrapure that 500 μ L are added
Water, then it is separately added into 30 μ L Fe2+The Tris-HCl buffer solution of solution and 500 μ L, excites, wave under the excitation wavelength of 515nm
Long range is 600~800nm, and slit width is all 10nm.
7. application of the porphyrin compound fluorescent molecule according to claim 5 in detection hydrogen peroxide and glucose,
It is characterized in that, when for detecting glucose: the TPPS for being 0.1M with porphyrin compound fluorescent molecule compound concentration obtained4It is water-soluble
Liquid；Pipette the 200 μ L TPPS4Aqueous solution is added 500 μ L ultrapure waters, then is separately added into 30 μ L Fe2+Solution and 500 μ L's
Tris-HCl buffer solution, obtains TPPS4-Fe2+Probe stock solution, to the TPPS4-Fe2+It is added in probe stock solution a certain amount of
Then the glucose of various concentration is added in glucose oxidase, observe the variation that fluorescence intensity occurs, can quench fluorescence.
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| CN110031440A (en) * | 2019-04-29 | 2019-07-19 | 滁州学院 | A kind of gas-sensitive type fluorescent optical sensor detection device and its application in grease type food inspection |
| CN111607100A (en) * | 2020-06-10 | 2020-09-01 | 苏州大学 | Crystalline material based on iron-based porphyrin ligand, preparation and application thereof |
| CN112028899A (en) * | 2020-08-31 | 2020-12-04 | 青海民族大学 | Preparation of TSPP and application thereof in detecting content of sulfur ions |
| CN114920765A (en) * | 2022-04-11 | 2022-08-19 | 南京农业大学 | Aryl boric acid substituted cationic porphyrin array sensor and preparation method and application thereof |
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| CN110031440A (en) * | 2019-04-29 | 2019-07-19 | 滁州学院 | A kind of gas-sensitive type fluorescent optical sensor detection device and its application in grease type food inspection |
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