CN113008853B - Method for in-situ marking and visual tracing of explosive based on fluorescent energetic molecules - Google Patents
Method for in-situ marking and visual tracing of explosive based on fluorescent energetic molecules Download PDFInfo
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- 239000002360 explosive Substances 0.000 title claims abstract description 68
- 230000000007 visual effect Effects 0.000 title claims abstract description 18
- 238000011065 in-situ storage Methods 0.000 title claims abstract description 13
- 238000000034 method Methods 0.000 title claims abstract description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 15
- 238000005516 engineering process Methods 0.000 claims abstract description 10
- 238000002372 labelling Methods 0.000 claims abstract description 10
- 230000003595 spectral effect Effects 0.000 claims abstract description 8
- 238000004020 luminiscence type Methods 0.000 claims abstract description 4
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- 238000001514 detection method Methods 0.000 claims description 13
- 238000010521 absorption reaction Methods 0.000 claims description 10
- 230000035945 sensitivity Effects 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 238000010276 construction Methods 0.000 claims description 4
- 238000006862 quantum yield reaction Methods 0.000 claims description 4
- 238000000862 absorption spectrum Methods 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 238000002189 fluorescence spectrum Methods 0.000 claims description 2
- 238000003384 imaging method Methods 0.000 claims description 2
- 238000011835 investigation Methods 0.000 claims 2
- 238000010791 quenching Methods 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 5
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- 238000012360 testing method Methods 0.000 description 4
- 239000011540 sensing material Substances 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000005474 detonation Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
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- JDFUJAMTCCQARF-UHFFFAOYSA-N tatb Chemical compound NC1=C([N+]([O-])=O)C(N)=C([N+]([O-])=O)C(N)=C1[N+]([O-])=O JDFUJAMTCCQARF-UHFFFAOYSA-N 0.000 description 2
- TZRXHJWUDPFEEY-UHFFFAOYSA-N Pentaerythritol Tetranitrate Chemical compound [O-][N+](=O)OCC(CO[N+]([O-])=O)(CO[N+]([O-])=O)CO[N+]([O-])=O TZRXHJWUDPFEEY-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- QEIQICVPDMCDHG-UHFFFAOYSA-N pyrrolo[2,3-d]triazole Chemical compound N1=NC2=CC=NC2=N1 QEIQICVPDMCDHG-UHFFFAOYSA-N 0.000 description 1
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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"
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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
- G01N21/645—Specially adapted constructive features of fluorimeters
- G01N21/6456—Spatial resolved fluorescence measurements; Imaging
- G01N21/6458—Fluorescence microscopy
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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"
- G01N2021/6439—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" with indicators, stains, dyes, tags, labels, marks
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Abstract
The invention discloses an in-situ labeling and visual tracing method for explosives based on fluorescent energetic molecules, which comprises the following steps: step 1: constructing fluorescent energetic molecules; and 2, step: investigating the spectral property of the fluorescent energetic molecule; and 3, step 3: optimizing the luminescence signal of the fluorescence energetic molecule; and 4, step 4: and (3) marking and tracing the explosive by the fluorescent energetic molecules. The invention provides a method for enlarging a conjugated system of an explosive aiming at the marking and tracing technology of the explosive, and regulates and controls the chemical position of a nitro group to be used as a chromogenic group so as to enhance the light absorption efficiency, so that the nitro group can not quench the fluorescence of explosive molecules but enhance the fluorescence of the explosive molecules, thereby realizing the marking and tracing of the explosive.
Description
Technical Field
The invention relates to the technical fields of energetic materials, public safety, environmental protection and the like, and an embodiment of the invention relates to the analysis of the existence and the content of a fluorescent energetic molecule through a self fluorescent signal of the fluorescent energetic molecule, and the fluorescent energetic molecule can be doped in other explosives to further mark and trace the other explosives so as to improve the detection sensitivity and the naked eye visibility of the other explosives.
Background
Explosives, as a high energy material, are widely used in the fields of weapon systems, civil blasting, etc. due to their high energy characteristics and destructive effects. The analysis and detection of the explosive not only relate to the quality control of the development and production process, but also relate to the environmental detection of manufacturing sewage or using sites, and in addition, the analysis and detection of the explosive plays an important role in terrorist explosion early warning in the field of public safety. However, the explosive molecules themselves have weak conjugated systems or strong electron-withdrawing groups, so that the explosive molecules themselves do not actively emit signals. Currently, in order to realize highly sensitive in-situ detection of explosives, an additional design is usually required to prepare a fluorescent sensing material, and the molecules of the explosives are indirectly detected by using fluorescence quenching caused by the interaction of the fluorescent sensing material and the molecules of the explosives. Most fluorescent materials are conventional materials, cannot be used as energetic materials by themselves, and when the fluorescent materials are doped into explosives, the energy of the explosives is reduced, so that the high-energy characteristics of the explosives are not maintained. The novel material with both fluorescence and high energy, namely the fluorescent energetic molecules, is developed, so that the high energy of the explosive can be kept, the explosive can be endowed with an actively emitted signal, and the analysis detection and naked eye identification of the explosive can be realized without additionally preparing a sensing material. However, so far, no report on the use of fluorescent energetic molecules for explosive labeling and tracing has been found.
Disclosure of Invention
At present, the self-conjugated system of explosive molecules is weaker, or the explosive molecules have strong electron-withdrawing nitro groups, so that the explosive molecules do not have actively-emitted fluorescent signals, and the explosive molecules cannot be directly subjected to in-situ detection and naked eye identification. Therefore, the invention provides the fluorescent energetic molecules based on the fluorescence emission signals, which are used for in-situ labeling and visual tracing analysis of explosive molecules.
In order to achieve the purpose, the invention adopts the following technical scheme:
in order to realize the autofluorescence emission of the nitro-explosive, expand the conjugated system of explosive molecules, generate fluorescence enhancement signals, investigate the fluorescence properties of the nitro-explosive, optimize the generation conditions of the fluorescence signals, dope the nitro-explosive into other explosive molecules, investigate the marking effect and the tracing condition of the nitro-explosive in a solution or solid state, and finally form a high-sensitivity marking and visual tracing technology for the nitro-explosive based on the fluorescence energetic molecules.
In order to obtain a novel dissolving technology and a novel dissolving method aiming at TATB, the invention adopts the following specific technical scheme:
(1) Construction of novel fluorescent energetic molecules: in order to enable the nitrobenzene explosive molecules to have a fluorescence effect, a conjugated system of the nitrobenzene explosive molecules is firstly expanded, and the number of phenyl condensed rings is not less than 3. Then, a nitro group is introduced to serve as a chromophore, and the position of the nitro group is regulated so that the absorption coefficient and the luminous efficiency of explosive molecules are high. In addition, the introduced nitro group is also used as an explosion-causing group, so that the energy level of the fluorescent molecule is improved, and the fluorescent molecule becomes a fluorescent energetic molecule.
(2) Examination of spectral properties of fluorescent energetic molecules: and (3) observing the ultraviolet absorption spectrum and the maximum absorption wavelength of the fluorescent energetic molecules by using an ultraviolet absorption spectrometer, observing the fluorescent emission spectrum and the maximum emission wavelength of the fluorescent energetic molecules by using the fluorescent spectrometer, and calculating the spectral parameters of the fluorescent energetic molecules, such as the molar absorption coefficient, the Stokes shift, the fluorescence quantum yield and the like.
(3) Optimizing the luminescence signal of the fluorescent energetic molecule: the influence of different solvents such as acetonitrile, methanol, dimethyl sulfoxide, dimethyl formamide and the like on fluorescence signals of the fluorescent energetic molecules is inspected, the influence of different water contents on the fluorescence signals of the fluorescent energetic molecules is analyzed, and the influence of different pH values on the fluorescence signals of the fluorescent energetic molecules is researched. The conditions are optimized such that the fluorescent energetic molecule has an optimal fluorescence emission signal.
(4) Marking and tracing explosive by fluorescent energetic molecules: a certain content of fluorescent energetic molecules is doped into other non-luminous explosives such as TNT, HMX and PETN. Establishing a liquid sample high-sensitivity marking technology, and inspecting the detection sensitivity of fluorescent energetic molecules to other explosive in-situ marks by using a fluorescence spectrometer. And establishing a visual tracing technology of the solid sample, and inspecting the sensitivity of the fluorescent energetic molecules to the visual detection of other explosives by adopting a fluorescent microscopic imaging technology.
Compared with the prior art, the invention has the following beneficial effects:
the invention provides a method for enlarging a conjugated system of an explosive aiming at the marking and tracing technology of the explosive, and regulates and controls the chemical position of a nitro group to be used as a chromogenic group so as to enhance the light absorption efficiency, so that the nitro group can not quench the fluorescence of explosive molecules but enhance the fluorescence of the explosive molecules, thereby realizing the marking and tracing of the explosive.
Drawings
Fig. 1 is a flow chart of a BPTAP construction strategy, where a: extended conjugated system, b: introducing nitro group.
FIG. 2 shows fluorescence signals of BPTAP in different solvents, wherein 1: DMSO,2: DMF,3: acetonitrile, 4: methanol.
FIG. 3 is the optimum solubility of TATB for the novel solvent system (10 g).
FIG. 4 shows the morphology of BPTAP itself.
Detailed Description
The present invention will be further described with reference to the following examples, which are intended to illustrate only some, but not all, of the embodiments of the present invention. Based on the embodiments of the present invention, other embodiments used by those skilled in the art without any creative effort belong to the protection scope of the present invention.
Example 1
(1) Construction of BPTAP fluorescent energetic molecules: the tetra-aza-pentalene is taken as a core structure, phenyl and pyridine are respectively arranged on two sides to form a condensed ring structure with 4 rings connected in parallel, and the conjugation degree of a molecular system is enlarged (figure 1). Four nitro groups are introduced into 2,4,8 and 10 positions of benzo-1, 3a,6 a-tetraazapentalenopyridine, and the introduced four nitro groups are used as chromophore to improve absorption and luminescence efficiency. On the other hand, the introduced four nitro groups serve as detonating groups to increase the energy level, so that BPTAP has good thermal stability (the thermal decomposition temperature is 375 ℃) and detonation energy (the detonation velocity is 7.43 km/s).
(2) Spectral properties of BPTAP study:
by ultraviolet absorptionThe spectrum obtained by the spectrometer has the ultraviolet absorption spectrum range of 400-600nm and the maximum absorption wavelength of 460nm. The fluorescence emission spectrum range of the BPTAP obtained by a fluorescence spectrometer is 450-650nm, and the maximum emission wavelength is 508nm. The calculated molar absorption coefficient of BPTAP is 4.12X 10 4 M -1 ·cm -1 Stokes shift 48nm, fluorescence quantum yield 0.24.
(3) Fluorescence signal optimization of BPTAP: when 5. Mu.g of BPTAP was dissolved in 10mL of different solvents such as acetonitrile, methanol, dimethyl sulfoxide, dimethylformamide and the like, the fluorescence intensity of BPTAP in acetonitrile, methanol, dimethyl sulfoxide and dimethylformamide was found to be 105.77, 16.75, 4.99 and 5.33 respectively, and the fluorescence intensity of BPTAP in acetonitrile was found to be the strongest (FIG. 2). The fluorescence intensity is respectively reduced by 21%, 64% and 73% by adding 10%, 20% and 40% of water into the BPTAP solvent system, and the fluorescence signal of the BPTAP is obviously reduced by increasing the water content. The fluorescence signals of BPTAP were tested in different pH environments, e.g., pH 5, 6, 7, 8, 9, etc., and it was found that the fluorescence intensity of BPTAP decreased significantly when the pH was greater than 7.0. Through condition optimization, the optimal conditions of the BPTAP fluorescent signal are acetonitrile solution, do not contain water and have the pH value of not more than 7.0.
(4) Labelling and tracing studies of BPTAP on explosives:
the fluorescence signals of BPTAP with different concentrations (0.1-1 mug/mL) are tested (figure 3), and the fluorescence intensity and the concentration have good linear relation, and the correlation coefficient R 2 =0.998, detection limit is 0.03ppm. Aiming at the liquid sample marking test of other explosives, 1mg of BPTAP is respectively doped in 100mg of TNT and HMX, and the test finds that the concentration range of TNT and HMX is 1-50 mu g/mL, the marking of TNT and HMX has good linear relation and the correlation coefficient R 2 =0.997, and the detection limits of the BPTAP-based marker for TNT and HMX are 0.48ppm and 0.15ppm, respectively. Aiming at a visual tracing test (figure 4) of a solid sample of other explosives, 5mg of BPTAP is respectively doped in 100mg of TNT and HMX, the mixture is uniformly mixed and then placed under a fluorescence microscope for testing, and uniform and obvious fluorescence signals in the mixed explosive sample are found, which indicates that the BPTAP realizes the visual tracing of TNT and HMX.
2,4,8, 10-tetranitrobenzo-1, 3a,6 a-tetraazapentalenopyridine (BPTAP) is used as a fluorescent energetic molecule, a large condensed ring system and 4 nitro group groups are provided, the maximum emission wavelength of the BPTAP is 508, the fluorescence quantum yield is 0.24, obvious green fluorescence is shown in both liquid state and solid state, a in figure 4 is the shape of the BPTAP, and b in figure 4 is the fluorescence emission effect of the BPTAP under an ultraviolet lamp. For the highly sensitive labeling of liquid samples, the sensitivity of BPTAP itself was 0.03ppm, and the sensitivity to TNT and HMX labels was 0.48ppm and 0.15ppm, respectively. Aiming at the visual tracing of a solid sample, the crystal of BPTAP has bright fluorescence, and obvious visual effect is shown by doping 5% of BPTAP into TNT and HMX solid powder, wherein c in fig. 4 is the original appearance of the TNT explosive doped with BPTAP, and d in fig. 4 is the fluorescence emission and tracing effect of the BPTAP doped in the TNT under an ultraviolet lamp.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents and improvements made within the spirit and principle of the present invention are intended to be included within the scope of the present invention.
Claims (5)
1. The method for in-situ marking and visual tracing of explosives based on fluorescent energetic molecules is characterized by comprising the following steps:
step 1: constructing fluorescent energetic molecules;
step 2: investigating the spectral property of the fluorescent energetic molecule;
and 3, step 3: optimizing the luminescence signal of the fluorescence energetic molecule;
and 4, step 4: marking and tracing the explosive by fluorescent energetic molecules;
in step 1, the construction of fluorescent energetic molecules comprises: enlarging the conjugated system of nitrobenzene explosive molecules, wherein the number of condensed phenyl rings is not less than 3; the introduction of nitro group as chromophore and the regulation of nitro position makes the explosive molecule possess high light absorption coefficient and luminous efficiency.
2. The method for in-situ labeling and visual tracing of explosives based on fluorescent energetic molecules as claimed in claim 1 wherein in step 2, the investigation of the spectral properties of fluorescent energetic molecules comprises: and calculating the molar absorption coefficient, stokes shift and fluorescence quantum yield spectral parameters of the fluorescent energetic molecules.
3. The method for in-situ labeling and visual tracing of explosives based on fluorescent energetic molecules as claimed in claim 2, wherein the investigation of the spectral properties of the fluorescent energetic molecules specifically comprises: and (3) adopting an ultraviolet absorption spectrometer to investigate the ultraviolet absorption spectrum and the maximum absorption wavelength of the fluorescent energetic molecules, and adopting a fluorescence spectrometer to investigate the fluorescence emission spectrum and the maximum emission wavelength of the fluorescent energetic molecules.
4. The method for in-situ labeling and visual tracing of explosives based on fluorescent energetic molecules as claimed in claim 1 wherein in step 3, the luminescent signal of fluorescent energetic molecules is optimized, comprising: and (3) investigating the influence of different solvents on the fluorescence signal of the fluorescent energetic molecule, analyzing the influence of different water contents on the fluorescence signal of the fluorescent energetic molecule, and researching the influence of different pH values on the fluorescence signal of the fluorescent energetic molecule.
5. The method for in-situ labeling and visual tracing of explosives based on fluorescent energetic molecules as claimed in claim 1 wherein in step 4, the labeling and tracing of explosives by fluorescent energetic molecules comprises: doping fluorescent energetic molecules into other non-luminous explosives, establishing a high-sensitivity marking technology for a liquid sample, and inspecting the detection sensitivity of the fluorescent energetic molecules to the in-situ marking of the other explosives by using a fluorescence spectrometer; establishing a visual tracing technology of the solid sample, and inspecting the sensitivity of the fluorescent energetic molecules to other explosive visual detection by adopting a fluorescent microscopic imaging technology.
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