CN106883843A - A kind of fluorescence probe and its application and preparation in explosive is detected - Google Patents
A kind of fluorescence probe and its application and preparation in explosive is detected Download PDFInfo
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/127—Preparation from compounds containing pyridine rings
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- 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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- 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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- 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 relates to a class, in the presence of the explosives such as nitro compound there is the fluorescence probe of Quenching in fluorescence intensity.The structure of described fluorescence probe is
Description
Technical field
The present invention relates to fluorescence probe field, and in particular to a kind of synthetic method of fluorescence probe and its detection
Application in the explosives such as nitro compound.
Background technology
All parts of the world terrorist action in recent years is becoming increasingly rampant, such as 2004 Russian aircraft case of explosions,
Bombay train case of explosion in 2006, India's vegetarian pul case of explosions in 2008 and Moscow metro in 2010 are quick-fried
Fried case etc., this is manufactured because the explosive weapon based on nitro compound is very easy, but they but may be used
To cause huge harm and loss, especially AT STATION, the dense population areas such as airport.Therefore, develop high
Effect sensitively detects that the method for the explosives such as nitro compound has turned into and concerns global safety problem and carried
Upper schedule.
At present, the method for the detection explosive for having grown up is a lot, such as chemical on-the-spot test method, chemistry
Electric-resistivity method, portable mass spectrography, combined gas chromatography mass spectrometry, GC -ECD, surface enhanced
Raman spectroscopy, nuclear quadrupole resonance method, hot fast neutron analysis method, ion mobility spectrometry and x-ray method etc..
However, most detection method cost input is higher, detection process is excessively complicated, and these factors are all serious
Constrain application of some methods in actually detected.Such as, although chemical on-the-spot test method detection specificity
It is very strong but sensitivity is not high, cannot also realize remote detection；X-ray method can detect a large amount of hiding blasts
Property device, portable mass spectrography can be recognized accurately the chemical constitution of explosive, but the characteristics of its hardware intensive type
Reduce the practicality in complex environment.
Fluorescent probe technique is one of means of explosive such as effective detection nitro compound, because the technology phase
Technical requirement is not high for, it is easy to practical, and detection sensitivity is high, to many explosives point
Son even some particular functional groups have recognition reaction.At present, 2- ethynyl pyridine structures are still not based on
Five butterfly alkene quinones fluorescence probes synthetic method and application, therefore, patent describes such fluorescence probe
Synthetic method and its application in the detection explosive such as nitro compound.
The content of the invention
It is an object of the invention to provide a kind of system of the fluorescence probe that can detect the explosives such as nitro compound
Preparation Method and application, the fluorescence probe are with five butterfly alkene quinones obtained in condensed-nuclei aromatics and 2- acetenyls
Pyridine lithium is a kind of fluorescence probe with explosive functions such as detection nitro compounds of Material synthesis.
The purpose of the present invention is accomplished in the following manner：
A kind of synthetic method of the fluorescence probe with explosive functions such as detection nitro compounds, including it is following
Step：
(1) with condensed-nuclei aromatics, acetic acid and 1,4-benzoquinone as raw material, synthesis obtains triptycene quinones II；
(2) with condensed-nuclei aromatics, acetic acid, compound ii and tetrachloroquinone as raw material, synthesis obtains five butterfly alkene quinones
Class compound III；
(3) with 2- ethynyl pyridines, n-BuLi, n-hexane and tetrahydrofuran as raw material, synthesis is obtained
2- ethynyl pyridine lithiums, i.e. compounds Ⅳ；
(4) with compound III, tetrahydrofuran and compounds Ⅳ as raw material, synthesis obtains fluorescence probe precursor,
That is compound V；
(5) with compound V, stannous chloride, acetic acid and acetone as raw material, the fluorescence needed for synthesis is obtained is visited
Pin, i.e., a kind of fluorescence probe with the explosive detection function such as nitro compound, its general structure I is as follows：
In formula I, R1~R4 is H, alkyl, aryl or containing heteroatomic substitution base.R1~R4 is alkane
It is alkyl, the aryl of C1~C20, the preferably alkyl of C1~C10, aryl when base, aryl；
R1~R4 is when containing hetero atom substituents, be sulfonic group, carboxyl, hydroxyl, halogen, amino, amido,
Alkoxy, cyano group or nitro.
The synthetic method of the above-mentioned fluorescence probe with the explosive detection function such as nitro compound, it is described
Condensed-nuclei aromatics in step (1), (2) is anthracene or anthracene substituent, and substitution base is for alkyl, aryl or containing miscellaneous original
The substitution base of son；It is alkyl, the aryl of C1~C20 when substitution base is alkyl, aryl, preferably C1~
The alkyl of C10, aryl；Substitution base is when containing hetero atom substituents, is sulfonic group, carboxyl, hydroxyl, halogen
Element, amino, amido, alkoxy, cyano group or nitro.
The synthetic method of the above-mentioned fluorescence probe with the explosive detection function such as nitro compound, it is described
Reaction condition in step (1) is that condensed-nuclei aromatics, acetic acid and 1,4-benzoquinone, condensed ring are added in there-necked flask
Aromatic hydrocarbons is 1 with the mol ratio of 1,4-benzoquinone:0.5~1:2；Agitator is started, 4~10h is heated to reflux, reacted cold
To room temperature, suction filtration, filter residue hot wash obtains compound ii after drying.
The synthetic method of the above-mentioned fluorescence probe with the explosive detection function such as nitro compound, it is described
Reaction condition in step (2) is that condensed-nuclei aromatics, acetic acid, compound ii and tetrachloro are added in there-necked flask
Benzoquinones, condensed-nuclei aromatics is 1 with the mol ratio of compound ii:0.5~1:2；Agitator is started, it is heated to reflux 30~
40h, after reaction is cooled to room temperature, suction filtration, filter residue is washed with ether, and compound III is obtained after drying.
The synthetic method of the above-mentioned fluorescence probe with the explosive detection function such as nitro compound, it is described
Reaction condition in step (3) is 2- ethynyl pyridines to be added in there-necked flask and is processed through anhydrous and oxygen-free
Tetrahydrofuran；Start agitator and reactant is cooled to -10~0 DEG C, under stirring and nitrogen protection
The hexane solution containing n-BuLi is added dropwise, the solution containing compounds Ⅳ is obtained.
The synthetic method of the above-mentioned fluorescence probe with the explosive detection function such as nitro compound, it is described
Reaction condition in step (4) is the tetrahydrochysene for compound III being added in there-necked flask and being processed through anhydrous and oxygen-free
Furans；Start agitator, stirring and nitrogen protection under be added dropwise (3) in obtain containing the molten of compounds Ⅳ
Liquid；At room temperature react 10~20h, with watery hydrochloric acid and after, with chloroform extract, organic phase anhydrous Na 2SO4
Chloroform is steamed after drying, compound V is obtained.
The synthetic method of the above-mentioned fluorescence probe with the explosive detection function such as nitro compound, it is described
Reaction condition in step (5) is addition compound V and the acetone in round-bottomed flask；Agitator is started, is dripped
Plus the acetic acid solution containing stannous chloride；20~30h is reacted at room temperature, reactant mixture is filtered, filter residue
Washed with NaHCO3, then dissolved with chloroform, chloroform is steamed after being dried through anhydrous magnesium sulfate, needed for obtaining
Fluorescence probe.
A kind of fluorescence probe prepared according to above-mentioned synthetic method.
According to fluorescence probe answering in the explosives such as detection nitro compound prepared by above-mentioned synthetic method
With.
Beneficial effects of the present invention：
The present invention reacts using by five butterfly alkene quinones obtained in condensed-nuclei aromatics and 2- ethynyl pyridines lithium
To prepare required fluorescence probe, the chloroformic solution of the fluorescence probe can occur in the presence of having nitro compound
Fluorescence-quenching, and be quenched degree and increase with the increase of nitro-compound concentration.Compared to existing
Some detection techniques, the fluorescence probe cost input in the present invention is less, and synthetic route is simple, post processing
It is convenient.
Fluorescence probe of the present invention can effectively combine nitro compound because it has big cavity structure,
The electron deficient performance of its electron rich structure and nitro compound determines that the two combines rear electric charge and part coupling occurs
Cooperation is used, and causes fluorescence to be quenched, so as to play a part of the explosives such as detection nitro compound.
Brief description of the drawings
Synthesize the flow chart of fluorescence probe o-IPP in Fig. 1 embodiments 1~5；
In Fig. 2 embodiments 6 fluorescence probe o-IPP after various concentrations nitrobenzene 10 minutes is added with 260
Fluorescence spectra when nm light is excited.
Specific embodiment
Embodiment is used to further illustrate the present invention, but the invention is not restricted to embodiment.
The synthesis of the triptycene quinone of embodiment 1：
Add 0.41g (2.30mmol) anthracene, 1.39g (12.86mmol) right in 100mL there-necked flasks
Benzoquinones and 40mL acetic acid.Agitator is started, 6h is heated to reflux, after reaction is cooled to room temperature, suction filtration, filter residue
With hot wash, 0.37g (1.30mmol) triptycene quinone is obtained after drying, yield is 56.6%.By matter
Spectrum,1H-NMR and12C-NMR nuclear magnetic spectrograms confirm that product is triptycene quinone.
The synthesis of the butterfly alkene quinone of embodiment 2 five：
0.18g (1.00mmol) anthracene, the butterflies of 0.28g (1.00mmol) three are added in 100mL there-necked flasks
Alkene quinone, 0.25g (1.00mmol) tetrachloroquinones and 60mL acetic acid.Agitator is started, 36h is heated to reflux,
After reaction is cooled to room temperature, suction filtration, filter residue is washed with ether, and the butterfly alkene of 0.26g (0.57mmol) five is obtained after drying
Quinone, yield is 56.5%.By mass spectrum,1H-NMR and12C-NMR nuclear magnetic spectrograms confirm that product is five
Butterfly alkene quinone.
The synthesis of the 2- ethynyl pyridines mile (compounds Ⅳ) of embodiment 3：
10mL there-necked flasks are placed in ice-water bath and logical nitrogen, 0.5mL (4.56mmol) 2- second is added
The tetrahydrofuran that alkynyl pyridine and 5mL are processed through anhydrous and oxygen-free.Start agitator and be cooled to reactant
0 DEG C, n-BuLi/n-hexane that 1.9mL concentration is 2.7M is dropwise added dropwise under stirring and nitrogen protection
Solution, obtains the solution containing compounds Ⅳ.Confirm to contain compounds Ⅳ in product by mass spectrum.
The synthesis of the fluorescence probe precursor o-IPP precursor of embodiment 4：
0.25g (0.54mmol) five butterfly alkene quinones and 40mL are added in 100mL there-necked flasks through anhydrous
The tetrahydrofuran of anaerobic treatment.Agitator is started, 7mL is dropwise added dropwise under stirring and nitrogen protection implements
The solution containing compounds Ⅳ obtained in example 3.16h is reacted at room temperature, with dilute salt that mass concentration is 10%
After acid is neutralized to pH=7, extracted with chloroform, organic phase anhydrous Na2SO4Chloroform is steamed after drying, is obtained
0.25g (0.37mmol) o-IPP precursor, yield is 69.4%.By mass spectrum,1H-NMR and12C-NMR nuclear magnetic spectrograms confirm that product is o-IPP precursor.
The synthesis of the fluorescence probe o-IPP of embodiment 5：
0.20g (0.30mmol) o-IPP precursor and 5mL third is added in 50mL round-bottomed flasks
Ketone.Agitator is started, it is the stannous chloride/acetic acid solution of 0.1mol/L that 10mL concentration is added dropwise.At room temperature
Reaction 24h, reactant mixture is filtered, filter residue saturation NaHCO3Solution is washed, then molten with chloroform
Solution, steams chloroform and obtains 0.12g (0.19mmol) fluorescence probe o-IPP after being dried through anhydrous magnesium sulfate, and yield is
63.0%.By mass spectrum,1H-NMR and12C-NMR nuclear magnetic spectrograms confirm that product is o-IPP.
The fluoroscopic examination of the o-IPP p-nitrophenyls of embodiment 6：
It is that 10 μM of o-IPP probe solutions for being dissolved in chloroform are added to by 3mL concentration
In the cuvette of 1cm × 1cm × 4cm, the nitrobenzene of different volumes is then separately added into so that it is final dense
Degree be respectively 0,195 μM, 244 μM, 732 μM, 1220 μM, 1830 μM, 2440 μM,
3250 μM, after 10 minutes, exciting light selects 260nm, and the fluorescence of working solution is measured with XRF
Spectrum is as shown in Figure 2.Fig. 2 shows that after adding nitrobenzene, fluorescence is significantly reduced at 385nm, and
And with the increase of nitrobenzene amount is added, Fluorescence-quenching is more obvious, thus o-IPP can be realized to nitre
The fluoroscopic examination of base benzene.
Conclusion：From the figures above and embodiment, fluorescence probe of the present invention has big cavity because of it
Structure and can effectively combine nitro compound, the electron deficient performance of its electron rich structure and nitro compound is determined
Determine the two and combined the generation part coupling of rear electric charge, cause fluorescence to be quenched, so as to play detection nitre
The effect of the explosives such as based compound.
Claims (10)
1. a kind of fluorescence probe, it is characterised in that：The structure of the fluorescence probe is as shown in formula I：
In formula I, R1~R4 is respectively H, alkyl, aryl or containing heteroatomic substitution base.
2. fluorescence probe according to claim 1, it is characterised in that：Described alkyl be C1~
The alkyl (the preferably alkyl of C1~C10) of C20；Aryl is phenyl or substituted phenyl, on phenyl
Substitution base for C1~C20 alkyl (the preferably alkyl of C1~C10), replace base number be
1~5；It is sulfonic group, carboxyl, hydroxyl, halogen, amino, amido, alkane containing heteroatomic substitution base
One or more in epoxide, cyano group or nitro.
3. the application of the fluorescence probe described in a kind of claim 1 or 2, it is characterised in that：Described is glimmering
Light probe can be used to detect the nitro compound in explosive, specifically, the fluorescence probe warp shown in formula I
After nitro compound effect, fluorescence intensity is quenched, so as to realize the detection of nitro compound.
4. the application of fluorescence probe according to claim 3, it is characterised in that：Nitro compound is
One kind or two in nitrobenzene, 2,4- dinitro benzenes, 2,4,6- trinitrophenols, 2,4,6- trinitrotoluenes
More than kind.
5. it is a kind of synthesize claim 1 or 2 described in fluorescence probe synthetic method, it is characterised in that
Comprise the following steps：
(1) with condensed-nuclei aromatics, acetic acid and 1,4-benzoquinone as raw material, synthesis obtains triptycene quinones II；
(2) with condensed-nuclei aromatics, acetic acid, compound ii and tetrachloroquinone as raw material, synthesis obtains five butterfly alkene
Quinones III；
(3) with 2- ethynyl pyridines, n-BuLi, n-hexane and tetrahydrofuran as raw material, synthesize
To 2- ethynyl pyridine lithiums, i.e. compounds Ⅳ；
(4) with compound III, tetrahydrofuran and compounds Ⅳ as raw material, synthesis obtains fluorescence probe precursor,
That is compound V；
(5) with compound V, stannous chloride, acetic acid and acetone as raw material, synthesis is obtained shown in formula I
Fluorescence probe.
6. method according to claim 5, it is characterised in that in described step (1), (2)
Condensed-nuclei aromatics be anthracene or anthracene substituent, substitution base in anthracene substituent is for alkyl, aryl or containing hetero atom
Substitution base, the position of substitution is one or more in 1~No. 8 position；
Described alkyl is the alkyl (the preferably alkyl of C1~C10) of C1~C20；Aryl is benzene
Base or substituted phenyl, the alkyl that replacing on phenyl, base was C1~C20 be (preferably C1~C10's
Alkyl), the number for replacing base is 1~5；Containing it is heteroatomic substitution base be sulfonic group, carboxyl, hydroxyl,
One or more in halogen, amino, amido, alkoxy, cyano group or nitro.
7. method according to claim 5, it is characterised in that anti-in described step (1)
It is to add condensed-nuclei aromatics, acetic acid and 1,4-benzoquinone, condensed-nuclei aromatics to be rubbed with acetic acid in there-necked flask to answer condition
You are than being 1:0.25~1:1, condensed-nuclei aromatics is 1 with the mol ratio of 1,4-benzoquinone:0.5~1:2；
Agitator is started, 4~10h is heated to reflux, after reaction is cooled to room temperature, suction filtration, filter residue hot water
Washing, obtains compound ii after drying；
Reaction condition in described step (2) be in there-necked flask add condensed-nuclei aromatics, acetic acid,
Compound ii and tetrachloroquinone, condensed-nuclei aromatics are 1 with the mol ratio of acetic acid:0.25~1:1, condensed-nuclei aromatics with
The mol ratio of compound ii is 1:0.5~1:2, condensed-nuclei aromatics is 1 with the mol ratio of tetrachloroquinone:0.5~1:2；
Agitator is started, 30~40h is heated to reflux, after reaction is cooled to room temperature, suction filtration, filter residue ether
Washing, obtains compound III after drying.
8. method according to claim 5, it is characterised in that anti-in described step (3)
It is the tetrahydrofuran for 2- ethynyl pyridines being added in there-necked flask and being processed through anhydrous and oxygen-free, two to answer condition
The volume ratio of person is 1:10~1:20；
Start agitator and reactant is cooled to -10~0 DEG C, be added dropwise under stirring and nitrogen protection and contained
Hexane solution (the volume ratio of 2- ethynyl pyridines and the hexane solution containing n-BuLi of n-BuLi
It is 1:3~1:5) solution containing compounds Ⅳ, is obtained.
9. method according to claim 5, it is characterised in that anti-in described step (4)
It is the tetrahydrofuran for compound III being added in there-necked flask and being processed through anhydrous and oxygen-free to answer condition, the two
Mol ratio is 1:800~1:1500；
Start agitator, stirring and nitrogen protection under be added dropwise (3) in obtain containing the molten of compounds Ⅳ
Liquid；
10~20h is reacted at room temperature, after being neutralized to pH=7 with the watery hydrochloric acid that mass concentration is 10%, is used
Chloroform is extracted, and organic phase anhydrous Na 2SO4 steams chloroform after drying, and obtains compound V.
10. method according to claim 5, it is characterised in that anti-in described step (5)
It is addition compound V and the acetone in round-bottomed flask to answer condition, and the mol ratio of the two is 1:200~1:500；
Start agitator, dropwise addition concentration is 0.1mol/L stannous chlorides/acetic acid solution, the solution with it is foregoing
The volume ratio of acetone is 1:3~1:5；
20~30h being reacted at room temperature, reactant mixture being filtered, filter residue saturation NaHCO3 solution is washed
Wash, then dissolved with chloroform, chloroform is steamed after being dried through anhydrous magnesium sulfate, obtain the fluorescence shown in formula I and visit
Pin.
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| CN109836414A (en) * | 2019-03-26 | 2019-06-04 | 北京大学深圳研究生院 | A kind of five ptericne derivative, preparation method and its purposes in polyamines detection |
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| CN114656409B (en) * | 2022-03-17 | 2023-12-22 | 山东产研绿色与健康研究院有限公司 | Fluorescent material for rapidly detecting explosives, preparation method and application thereof |
| CN115260516A (en) * | 2022-08-17 | 2022-11-01 | 安徽工业大学 | Preparation method and application of fluorescent probe material based on sulfonyl calixarene structure |
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