CN109516979A - A method of utilizing fluorescence detection dinitric acid esters explosive - Google Patents
A method of utilizing fluorescence detection dinitric acid esters explosive Download PDFInfo
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Abstract
The present invention relates to a kind of methods using fluorescence detection dinitric acid esters explosive, comprising steps of providing the meta position pyridine compounds with following formula I:Liquid phase fluorescence probe is made in the meta position pyridine compounds；Object to be checked is added in liquid phase fluorescence probe and is detected, TEGDN and/or EGDN is contained in the object to be checked that fluorescence intensity weakens.Method according to the present invention using fluorescence detection dinitric acid esters explosive, it forms fluorescence probe using meta position pyridine compounds and is configured to solution, it directly will test object to be added in solution, cause the fluorescence spectrum of material change using fluorescence probe and TEGDN and/or EGDN effect, as long as therefore before and after comparing the variation of fluorescence color and intensity the detection to TEGDN and/or EGDN can be realized.
Description
Technical field
The present invention relates to fluorescence sense field, relate more specifically to a kind of using fluorescence detection dinitric acid esters explosive
Method.
Background technique
Terrorist is increasingly savage at present, and dinitric acid esters explosive triethylene glycol dinitrate (TEGDN) and second two
The manufacturing process of alcohol dinitrate (EGDN) is fairly simple and low in cost, becomes the explosive that terrorist is keen to.And TEGDN
It is all very big as harm of the plasticizer to soil, human body other than as explosive.
Highly sensitive sensor is the technical guarantee maintained social stability, and dinitric acid esters explosive is because lacking conjugation virtue
Fragrant ring forms pi-pi accumulation between hardly possible and probe molecule, so that detection becomes difficult.In nitrate esters explosive, PETN and NG because
Containing there are four with three nitrates, can be generated between probe molecule interaction force make it possible detection.Such as applicant
It is a kind of for detecting the high line fluorescence probe of NG the Applied Materials&Interfaces being published on ACS before on
Article (Lei Chen, Yixun Gao, Yuerong Wang, et al.Femtogram Level Detection of
Nitrate Ester Explosives via an 8-Pyrenyl-Substituted Fluorene Dimer Bridged
By a 1,6-Hexanyl Unit [J] .ACS Appl.Mater.Interfaces 2014,6:8817-8823), which is
Based on PET sensor mechanism using the nitrate on probe molecule and NG generate interaction force include dipole-dipole interaction,
Interaction of hydrogen bond, hydrophobic-hydrophobic interaction, thus achieve the purpose that detect NG, but the probe is in addition to generating NG
Also there is at least 10% or more response outside 80% or more response to other nitrate esters explosives.For another example it is published in
Article (the Ao Liu, Huan of the sucking action detection PETN with N atom pair nitro on Analytical Methods
Liu,Xin Peng,et al.Direct and Ultrasensitive Fluorescent Detection of PETN
Vapor Based on a Fuorene-dimer Probe Via a Synergic Backbone and Side-chain
Tuning [J] .Analytical Methods 2018,10:1029-1039), the probe is to other nitrates except PETN
Class explosive also has 30% or more response, and specificity is not fine.And the detection of TEGDN and EGDN mainly uses gas at present
The methods of phase chromatography, liquid chromatogram, mass spectrum and photoacoustic spectroscopy, detection process have the shortcomings that the time is long, sensitivity is low etc., cannot
Meet field quick detection needs.
Summary of the invention
The problems such as detection time in order to solve above-mentioned TEGDN of the existing technology and EGDN is long, the present invention is directed to mention
For a kind of method using fluorescence detection dinitric acid esters explosive.
Method of the present invention using fluorescence detection dinitric acid esters explosive, comprising steps of S1, is provided under having
The meta position pyridine compounds of Formulas I:
Wherein, Ar is the fluorophor selected from least one of following A1-A15；Q is any natural number greater than 0；
Wherein, R is alkyl；X is C, N, Si or P；N is any natural number greater than 0；S2, by the meta position pyridine chemical combination
Liquid phase fluorescence probe is made in object；Object to be checked is added in liquid phase fluorescence probe and detects by S3, and fluorescence intensity weakens to be checked
Contain triethylene glycol dinitrate (TEGDN) and/or dinitroglycol (EGDN) in object.
Particularly, meta position pyridine compounds according to the present invention, since the lone pair electrons of nitrogen on meta position pyridine can be with fluorescence
A big conjugated system is formed between group (Ar), in the presence of TEGDN and/or EGDN, which is coupled
Function influence is so that fluorescence changes.Contrastingly, ortho position with similar structure and nitrogen-atoms on contraposition pyridine
Lone pair electrons can not form conjugated system between fluorophor, thus can not be applied in detection method of the invention.Specifically,
Meta position pyridine compounds according to the present invention react with TEGDN and/or EGDN, that is, occur by meta position pyridine compounds to
The electric charge transfer of TEGDN and/or EGDN, while fluorophor also occurs to peripheral pyridine groups (point of meta position pyridine compounds
Son forms spherical, and fluorophor is in inside, and meta position pyridine is on the outside) energy transfer, weaken its fluorescence intensity, and TEGDN
And/or two nitrates of EGDN are easier to and meta position pyridine in the two sides of long-chain compared to other nitrate esters explosives
It is wound coupling between conjunction object, to realize the specific recognition to TEGDN and/or EGDN.
In the step S1, the meta position pyridine compounds are synthesized by suzuki reaction.
In the step S2, by the way that the meta position pyridine compounds are dissolved into organic solvent, that the liquid phase is made is glimmering
Light probe.
The concentration of meta position pyridine compounds in the liquid phase fluorescence probe is 0.5-1.5mg/mL.It is preferred real at one
It applies in example, which is 1mg/mL.
The organic solvent is tetrahydrofuran.
In the step S3, the blue-fluorescence that liquid phase fluorescence probe issues occurs after acting on TEGDN and/or EGDN
Fluorescent quenching.
The number q of meta position pyridine in the meta position pyridine compounds is 2-8.It should be understood that q is more, in step s3
Fluorescence intensity that efficiency is quenched is higher.In a preferred embodiment, efficiency is quenched higher than 30%, more preferably higher than 70% in this,
Most preferably it is higher than 90%.In addition, the number of the fluorophor in the meta position pyridine compounds is more, fluorescence signal variation is got over
Obviously.
The detectable concentration of TEGDN and/or EGDN in the object to be checked can be less than 10-3M.Preferably, the object to be checked
In TEGDN and/or EGDN minimal detectable concentration be 5.28 μM.
Method according to the present invention using fluorescence detection dinitric acid esters explosive utilizes meta position pyridine compounds shape
At fluorescence probe and be configured to solution, directly will test object and be added in solution, using fluorescence probe and TEGDN and/or
EGDN effect causes the fluorescence spectrum of material change, as long as therefore before and after comparing the variation of fluorescence color and intensity can be realized pair
The detection of TEGDN and/or EGDN.The detection method carries out at room temperature, quickly, sensitive, and entire detection can be realized in several seconds
Process, and detection process avoids the interference of other reagents without adding any auxiliary reagent.Moreover, the detection method is only right
TEGDN and EGDN has extraordinary specific detection effect.In short, of the invention utilizes fluorescence detection dinitric acid esters explosive
Method, have the characteristics that the detection of highly sensitive, highly selective and rapid field, provide technical guarantee for public security system safety check.
The present invention has the advantages that following apparent:
(1) fluorescence probe is easy a large amount of preparations and structure-controllable.The property has benefited from the probe and (does not need to add without mixing
Enter the pre-treatment solvents such as alkali or acid), the molecular structure of controllable (molecular structure stabilized).
(2) testing conditions are mild, can react at room temperature.Existing some detection means, such as gas-chromatography, magnetic field inspection
Survey etc. requires heating and is vaporized or decomposes, and complicated for operation to instrument requirements height, in comparison the present invention is more able to satisfy scene
Testing requirements.
(3) it is not necessarily to catalyst and sample pretreatment, so that detection is more credible more convenient.
(4) rapid reaction, it is easy to detect.TEGDN and EGDN solution is added drop-wise to probe solution, then measures its fluorescence light
The sensing to TEGDN and EGDN is realized in the variation of spectrum.
(5) selectivity is good.Probe only has a specificly-response to TEGDN and EGDN, and to other similar explosives and molten
Agent is almost without response.
In short, probe of the invention can act on the fluorescent emission wave for leading to probe therewith in the presence of TEGDN and EGDN
Long and fluorescence intensity changes, and the presence or absence of TEGDN and EGDN are determined according to the variation of fluorescence signal.PETN,NG,MN
And triethylene glycol, ethylene glycol etc. cannot cause the variation of its fluorescence signal.The present invention detected compared with chromatographic mass spectrometry is used in conjunction
Journey and the obvious simplification of operation, realize the specific detection to TEGDN and EGDN using the method for fluorescence sense for the first time.This
Outside, it is pre-processed also without to TEGDN and EGDN.
The TEGDN and EGDN in solution can be effectively detected using synthesized fluorescence probe, be a kind of new and effective
Fluorescence sense probe is expected to be used for strike terrorist and tests plasticizer TEGDN present in waste water and soil, while in phase
The design aspect for closing sensing material has directive significance.
Detailed description of the invention
Fig. 1 is 8Py-2F according to the present invention1H-NMR figure；
Fig. 2 is the Absorption and fluorescence spectrum figure of 8Py-2F and 2Py-F according to the present invention；
Fig. 3 is 8Py-2F according to the present invention and TEGDN effect front and back absorption and change in fluorescence situation；
Fig. 4 is 8Py-2F according to the present invention and EGDN effect front and back absorption and change in fluorescence situation；
Fig. 5 shows 8Py-2F according to the present invention and surveys to the selectivity of different nitrate esters explosives and interference with solvent
Examination；
Fig. 6 is 2Py-F according to the present invention1H-NMR figure；
Fig. 7 is 2Py-F according to the present invention13C-NMR figure；
Fig. 8 is 2Py-F according to the present invention and TEGDN effect front and back absorption and change in fluorescence situation；
Fig. 9 is 2Py-F according to the present invention and EGDN effect front and back absorption and change in fluorescence situation；
Figure 10 shows 2Py-F according to the present invention and surveys to the selectivity of different nitrate esters explosives and interference with solvent
Examination.
Specific embodiment
With reference to the accompanying drawing, presently preferred embodiments of the present invention is provided, and is described in detail.
Embodiment 1
The synthesis of 8Py-2F (- 2 fluorenes of 8 pyridine)
Under nitrogen protection, compound 1 (0.463g, 0.3mmol), 3- pyridine boronic acid (0.443g, 3.6mmol), Pd
(PPh3)4(117.6mg, 0.102mmol), K2CO3Aqueous solution (12mL, 2M), tetrahydrofuran 20mL, heating reflux reaction 72 are small
When.50mL saturated salt solution is poured into, tetrahydrofuran extracts three times.The anhydrous MgSO of organic phase4It is dry.Pillar layer separation is tied again
It is brilliant to obtain yellow solid (0.256g, yield 56.67%).
8Py-2F's1H-NMR is referring to Fig. 1.
The preparation of 8Py-2F fluorescence probe
The 8Py-2F of 3mg is dissolved into 3ml tetrahydrofuran solvent, liquid phase fluorescence probe is made.
The absorbing wavelength of fluorescence probe obtained be 235nm, launch wavelength 394nm, as shown in Figure 2.
The interaction of 8Py-2F fluorescence probe and TEGDN(A13 group)
TEGDN solution is instilled in liquid phase fluorescence probe solution, is uniformly mixed and is detected.
Compare the absorption of fluorescence probe and fluorescence spectrum before and after dropwise addition as shown in Figure 3, it can be seen that its absorption spectrum and
Fluorescence spectrum wavelength does not change substantially, and fluorescence intensity generation is significantly quenched, and it is 90.59% that efficiency, which is quenched,.
Embodiment 2
Fluorescence probe is prepared into according to embodiment 1.
The interaction of 8Py-2F fluorescence probe and EGDN(A13 group)
EGDN solution is instilled in liquid phase fluorescence probe solution, is uniformly mixed and is detected.
Compare the absorption of fluorescence probe and fluorescence spectrum before and after dropwise addition as shown in Figure 4, it can be seen that its absorption spectrum and
Fluorescence spectrum wavelength does not change substantially, and fluorescence intensity generation is significantly quenched, and it is 92.91% that efficiency, which is quenched,.
Embodiment 3
Fluorescence probe is prepared into according to embodiment 1.
The selectivity test of 8Py-2F fluorescence probe
Selection is the same as a series of nitrate esters explosive (pentaerythritol tetranitrate PETN, nitroglycerine NG, methyl nitrate
MN, TEGDN, EGDN) and a series of solvents (triethylene glycol TEG, ethylene glycol EG, ethyl alcohol EA, methanol MT, methylene chloride DCM),
It is acted on respectively with the tetrahydrofuran probe solution of the 8Py-2F of 1mg/mL, the variation of the fluorescence intensity of test effect front and back calculates
Its response efficiency.The selectivity test effect of 8Py-2F is as shown in Figure 5.As can be seen that 8Py-2F have to TEGDN and EGDN it is non-
Often good specificity, and other analytes are almost not responding to.Wherein, methanol MT and ethyl alcohol EA, ethylene glycol EG are common do
Solvent is disturbed, it should be the result shows that detection method according to the present invention will not be affected by the solvent；Triethylene glycol TEG and ethylene glycol EG
It, should be the result shows that detection method according to the present invention not will receive the influence of synthesis material for the synthesis material of TEGDN and EGDN.
Embodiment 4
The synthesis of 2Py-F (2 pyridines-fluorenes)
Under nitrogen protection, compound 2 (0.492g, 1mmol), 3- pyridine boronic acid (0.738g, 6mmol), Pd (PPh3)4
(196.45mg, 0.17mmol), K2CO3Aqueous solution (25mL, 2M), tetrahydrofuran 50mL, heating reflux reaction 36 hours.It pours into
50mL saturated salt solution, tetrahydrofuran extract three times.The anhydrous MgSO of organic phase4It is dry.Pillar layer separation recrystallizes white
Solid (0.403g, yield 82.55%).
2Py-F's1H-NMR referring to Fig. 6,13C-NMR is referring to Fig. 7.
The preparation of 2Py-F fluorescence probe
The 2Py-F of 3mg is dissolved into 3ml tetrahydrofuran solvent, liquid phase fluorescence probe is made.
The absorbing wavelength of fluorescence probe obtained be 234.5nm, launch wavelength 378nm, as shown in Figure 2.
The interaction of 2Py-F fluorescence probe and TEGDN(A3 group)
TEGDN solution is instilled in liquid phase fluorescence probe solution, is uniformly mixed and is detected.
Compare the absorption of fluorescence probe and fluorescence spectrum before and after dropwise addition as shown in Figure 8, it can be seen that its absorption spectrum and
Fluorescence spectrum wavelength does not change substantially, and fluorescence intensity generation is significantly quenched, and it is 30% that efficiency, which is quenched,.
Embodiment 5
Fluorescence probe is prepared into according to embodiment 4.
The interaction of 2Py-F fluorescence probe and EGDN(A3 group)
EGDN solution is instilled in liquid phase fluorescence probe solution, is uniformly mixed and is detected.
Compare the absorption of fluorescence probe and fluorescence spectrum before and after dropwise addition as shown in Figure 9, it can be seen that its absorption spectrum and
Fluorescence spectrum wavelength does not change substantially, and fluorescence intensity generation is significantly quenched, and it is 72.43% that efficiency, which is quenched,.
Embodiment 6
Fluorescence probe is prepared into according to embodiment 4.
The selectivity test of 2Py-F fluorescence probe
Selection is the same as a series of nitrate esters explosive (pentaerythritol tetranitrate PETN, nitroglycerine NG, methyl nitrate
MN, TEGDN, EGDN) and a series of solvents (triethylene glycol TEG, ethylene glycol EG, ethyl alcohol EA, methanol MT, methylene chloride DCM),
It is acted on respectively with the tetrahydrofuran probe solution of the 2Py-F of 1mg/mL, the variation of the fluorescence intensity of test effect front and back calculates it
Response efficiency.The selectivity test effect of 2Py-F is as shown in Figure 10.As can be seen that 2Py-F has very TEGDN and EGDN
Good specificity, and other analytes are almost not responding to.Wherein, methanol MT and ethyl alcohol EA, ethylene glycol EG are common interference
Solvent, should be the result shows that detection method according to the present invention will not be affected by the solvent；Triethylene glycol TEG and ethylene glycol EG are
The synthesis material of TEGDN and EGDN, should be the result shows that detection method according to the present invention not will receive the influence of synthesis material.
Above-described, only presently preferred embodiments of the present invention, the range being not intended to limit the invention, of the invention is upper
Stating embodiment can also make a variety of changes.Made by i.e. all claims applied according to the present invention and description
Simply, equivalent changes and modifications fall within the claims of the invention patent.The not detailed description of the present invention is
Routine techniques content.
Claims (8)
1. a kind of method using fluorescence detection dinitric acid esters explosive, which is characterized in that the method comprising the steps of:
S1 provides the meta position pyridine compounds with following formula I:
Wherein, Ar is the fluorophor selected from least one of following A1-A15；Q is any natural number greater than 0；
Wherein, R is alkyl；X is C, N, Si or P；N is any natural number greater than 0；
Liquid phase fluorescence probe is made in the meta position pyridine compounds by S2；
Object to be checked is added in liquid phase fluorescence probe and detects by S3, and three second two are contained in the object to be checked that fluorescence intensity weakens
Alcohol dinitrate and/or dinitroglycol.
2. the method according to claim 1, wherein in the step S1, reacting synthesis institute by suzuki
State meta position pyridine compounds.
3. the method according to claim 1, wherein in the step S2, by by the meta position pyridine
Conjunction object, which is dissolved into organic solvent, is made the liquid phase fluorescence probe.
4. according to the method described in claim 3, it is characterized in that, meta position pyridine compounds in the liquid phase fluorescence probe
Concentration is 0.5-1.5mg/mL.
5. according to the method described in claim 3, it is characterized in that, the organic solvent is tetrahydrofuran.
6. the method according to claim 1, wherein in the step S3, indigo plant that liquid phase fluorescence probe issues
After acting on triethylene glycol dinitrate and/or dinitroglycol fluorescent quenching occurs for color fluorescence.
7. the method according to claim 1, wherein the number of the meta position pyridine in the meta position pyridine compounds
Q is 2-8.
8. the method according to claim 1, wherein triethylene glycol dinitrate in the object to be checked and/or
The minimal detectable concentration of dinitroglycol is 5.28 μM.
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| CN110579470A (en) * | 2019-09-13 | 2019-12-17 | 中国科学院新疆理化技术研究所 | method for detecting explosives through real-time in-situ characterization of multimode coupling optical platform |
| CN113008853A (en) * | 2021-02-25 | 2021-06-22 | 中国工程物理研究院化工材料研究所 | Method for in-situ marking and visual tracing of explosive based on fluorescent energetic molecules |
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