CN109232627A - There are the fluorescent chemicals of sensing function and the preparation method and application of fluorescence sense film to gas phase acetone and peroxidating explosive - Google Patents
There are the fluorescent chemicals of sensing function and the preparation method and application of fluorescence sense film to gas phase acetone and peroxidating explosive Download PDFInfo
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- CN109232627A CN109232627A CN201811315218.0A CN201811315218A CN109232627A CN 109232627 A CN109232627 A CN 109232627A CN 201811315218 A CN201811315218 A CN 201811315218A CN 109232627 A CN109232627 A CN 109232627A
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- compound
- layer separation
- methylene chloride
- pillar layer
- acetone
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 title claims abstract description 130
- 239000002360 explosive Substances 0.000 title claims abstract description 45
- 239000000126 substance Substances 0.000 title claims abstract description 39
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 87
- 238000000034 method Methods 0.000 claims abstract description 31
- 238000001514 detection method Methods 0.000 claims abstract description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 129
- 239000007789 gas Substances 0.000 claims description 62
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical class CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 58
- 238000000926 separation method Methods 0.000 claims description 48
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 41
- 150000001875 compounds Chemical class 0.000 claims description 39
- 239000003480 eluent Substances 0.000 claims description 34
- 239000002904 solvent Substances 0.000 claims description 31
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- 239000000243 solution Substances 0.000 claims description 27
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 24
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- 229940125904 compound 1 Drugs 0.000 claims description 20
- 229940126214 compound 3 Drugs 0.000 claims description 20
- 229940125898 compound 5 Drugs 0.000 claims description 20
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 claims description 16
- 229940125782 compound 2 Drugs 0.000 claims description 16
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims description 16
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- 229910052786 argon Inorganic materials 0.000 claims description 12
- 239000011159 matrix material Substances 0.000 claims description 12
- 238000002390 rotary evaporation Methods 0.000 claims description 11
- CTFNJPHOILFHEL-UHFFFAOYSA-N CC1=C(C=CC=C1)[P] Chemical compound CC1=C(C=CC=C1)[P] CTFNJPHOILFHEL-UHFFFAOYSA-N 0.000 claims description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 239000005725 8-Hydroxyquinoline Substances 0.000 claims description 8
- CQHNJWAZNZBMMO-UHFFFAOYSA-N B(O)(O)O.IC1=CC=CC=C1 Chemical compound B(O)(O)O.IC1=CC=CC=C1 CQHNJWAZNZBMMO-UHFFFAOYSA-N 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- WEUCTTBUEWINIJ-UHFFFAOYSA-N acetic acid;zinc;dihydrate Chemical compound O.O.[Zn].CC(O)=O WEUCTTBUEWINIJ-UHFFFAOYSA-N 0.000 claims description 8
- 150000008065 acid anhydrides Chemical class 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 229940043279 diisopropylamine Drugs 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 8
- KUFWTXSQQKDMAI-UHFFFAOYSA-N ethynylsilicon Chemical compound [Si]C#C KUFWTXSQQKDMAI-UHFFFAOYSA-N 0.000 claims description 8
- 150000002460 imidazoles Chemical class 0.000 claims description 8
- 229960003540 oxyquinoline Drugs 0.000 claims description 8
- 229910000160 potassium phosphate Inorganic materials 0.000 claims description 8
- 235000011009 potassium phosphates Nutrition 0.000 claims description 8
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
- 239000011574 phosphorus Substances 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 claims description 6
- 239000011521 glass Substances 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
- 238000001704 evaporation Methods 0.000 claims description 5
- 230000008020 evaporation Effects 0.000 claims description 5
- 150000003973 alkyl amines Chemical class 0.000 claims description 4
- 238000010828 elution Methods 0.000 claims description 4
- 239000011550 stock solution Substances 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims description 3
- 238000000576 coating method Methods 0.000 claims description 3
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 claims description 3
- 239000000741 silica gel Substances 0.000 claims description 3
- 229910002027 silica gel Inorganic materials 0.000 claims description 3
- 125000005595 acetylacetonate group Chemical group 0.000 claims description 2
- 229920002521 macromolecule Polymers 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 230000035945 sensitivity Effects 0.000 abstract description 9
- 230000003287 optical effect Effects 0.000 abstract description 5
- 238000013461 design Methods 0.000 abstract description 4
- 238000011084 recovery Methods 0.000 abstract description 4
- 238000009833 condensation Methods 0.000 abstract description 3
- 230000005494 condensation Effects 0.000 abstract description 3
- 238000007614 solvation Methods 0.000 abstract description 3
- 238000011896 sensitive detection Methods 0.000 abstract description 2
- 239000010408 film Substances 0.000 description 52
- 230000002194 synthesizing effect Effects 0.000 description 24
- 239000007850 fluorescent dye Substances 0.000 description 17
- 238000012360 testing method Methods 0.000 description 14
- 238000003756 stirring Methods 0.000 description 12
- 230000004044 response Effects 0.000 description 11
- 241000736199 Paeonia Species 0.000 description 8
- 235000006484 Paeonia officinalis Nutrition 0.000 description 8
- 150000003949 imides Chemical class 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RKFFUJHJOUYEKT-UHFFFAOYSA-N boron;quinoline Chemical compound [B].N1=CC=CC2=CC=CC=C21 RKFFUJHJOUYEKT-UHFFFAOYSA-N 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- -1 Aminomethyl phenyl Chemical group 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 238000001914 filtration Methods 0.000 description 4
- 230000001376 precipitating effect Effects 0.000 description 4
- ZTLXICJMNFREPA-UHFFFAOYSA-N 3,3,6,6,9,9-hexamethyl-1,2,4,5,7,8-hexaoxonane Chemical compound CC1(C)OOC(C)(C)OOC(C)(C)OO1 ZTLXICJMNFREPA-UHFFFAOYSA-N 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- DAEAPNUQQAICNR-GFCOJPQKSA-N dadp Chemical compound C1=NC=2C(N)=NC=NC=2N1C1C[C@H](O)[C@@H](COP(O)(=O)OP(O)(O)=O)O1 DAEAPNUQQAICNR-GFCOJPQKSA-N 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 238000001917 fluorescence detection Methods 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 238000007689 inspection Methods 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 238000001871 ion mobility spectroscopy Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- 230000005311 nuclear magnetism Effects 0.000 description 2
- QNIVIMYXGGFTAK-UHFFFAOYSA-N octodrine Chemical compound CC(C)CCCC(C)N QNIVIMYXGGFTAK-UHFFFAOYSA-N 0.000 description 2
- 229960001465 octodrine Drugs 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 241000220225 Malus Species 0.000 description 1
- 235000011430 Malus pumila Nutrition 0.000 description 1
- 235000015103 Malus silvestris Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 240000008790 Musa x paradisiaca Species 0.000 description 1
- 235000018290 Musa x paradisiaca Nutrition 0.000 description 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 241000220324 Pyrus Species 0.000 description 1
- 238000001069 Raman spectroscopy Methods 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 239000012491 analyte Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 150000001638 boron Chemical class 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001548 drop coating Methods 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000011540 sensing material Substances 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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"
- 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
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- 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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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- 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
- C09K2211/104—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with other heteroatoms
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- 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
- C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
-
- 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
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Physics & Mathematics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Optics & Photonics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Molecular Biology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
The invention discloses have the fluorescent chemicals of sensing function and the preparation method and application of fluorescence sense film to gas phase acetone and peroxidating explosive, the molecular channel formed after being accumulated on a molecular scale using nonplanar structure, using the phenomenon that capillary condensation and solvation, realize acetone steam, the sensitive, highly selective of peroxidating explosive steam, recovery and stability recognition detection at room temperature, substantially solve the problems, such as that operating temperature is high when detection existing for previous methods, and the design of the fluorescence sense film to have excellent performance provides new thinking.Preparation method of the present invention is easy to operate, reaction condition is mild, prepared fluorescent chemicals photochemistry, thermodynamic stability are good, obtained fluorescence sense film high sensitivity, the good, long service life of selectivity, it is a kind of excellent fluorescence sense film, the Sensitive Detection that may be implemented to acetone steam and peroxidating explosive is used in combination in this kind of film and Commercial optical instrument.
Description
Technical field
The invention belongs to small molecule fluorescent sense film field of material technology, it is related to a kind of fluorescent chemicals and glimmering based on this
The preparation method and application of the fluorescence sense film of optical compounds, and in particular to a kind of pair of gas phase acetone and peroxidating explosive have
The fluorescent chemicals of sensing function and the preparation method and application of fluorescence sense film.
Background technique
In recent years, due to effective chemical property and low cost etc., so that acetone becomes the important materials of organic synthesis, quilt
It is widely used in industrial production, laboratory and medical industry.But acetone is a kind of colourless, volatile, inflammable gas, in air
Middle exposure easily becomes acetone steam, and Long Term Contact can cause damages to human health, gently then may lead eyes and throat
Stimulation, and cause the symptoms such as nausea, headache, vomiting, central nervous system heavy then that the mankind can be damaged, or even can be to people
The liver of body, kidney, pancreas cause non-response damage；Meanwhile the unregulated exhaust in acetone or vehicle exhaust pollutes owner
One of form, it is considered to be potential danger carcinogenic substance and important pollutant；In addition, the one of acetone or animal body metabolism
Kind product, concentration can reflect the body condition of organism, can be used for the early stage quick nondestructive of the diseases such as lung cancer, diabetes
Detection；More importantly acetone still synthesize be often used in the attack of terrorism the peroxidating with mass destruction power it is quick-fried
One of the most important raw material of fried object, peroxidating explosive can be reduced by the detection to acetone gas and gives mankind's bring calamity
It is difficult.Therefore, from environmental protection and human health and the angle of reduction terrorism, develop inexpensive, fast in real time
Speed, method is convenient, accurately and reliably acetone analyzing detecting method is quick for the early stage of crime prevention, environmental protection and disease
Nodestructive testing undoubtedly has very important significance.
Various detection techniques or method has been developed in importance based on acetone, up to the present, people.Gas
The techniques or methods such as matter combination, ion mobility spectrometry, surface-enhanced Raman, nuclear magnetic resonance, resistance type sensor are all successfully reported
Road.However, these methods often exist cumbersome, high cost, sensitivity not enough, poor selectivity, it is not portable the deficiencies of, it is difficult
It is used with putting it over.For example, resistance type sensor burning the hotest is studied at present, although showing higher detection to acetone
Sensitivity, but its main deficiency is to need to carry out under higher operating temperature (200-600 degrees Celsius), and preparation process is more
It is complicated, it is difficult to meet practical application.Therefore, develop it is a kind of it is highly sensitive at room temperature, highly selective, repeatable, response and restore speed
The Detection Techniques for spending fast acetone gas have and its important actual combat value and the inexorable trend of acetone sensor development.
It is well known that fluorescence sense is one kind after ion mobility spectrometry, internationally recognized a new generation's microscratch amount Detection Techniques.However,
According to literature survey, the acetone Detection Techniques based on fluorescence sense means are rarely reported.In addition, existing fluorescence detection technology is still
The disadvantages of that there are sensitivity is not high, anti-interference ability is poor, gas phase detection is more difficult, study carefully its be in the nature sensing material performance not
It is good, so it is of crucial importance to develop the excellent fluorescent material of sensing capabilities.
Imide derivatives are with its excellent photoelectric properties, photochemical stability, thermal stability in photoelectric functional material
It material, fluorescence sense and the fields such as catalyzes and synthesizes and gets more and more people's extensive concerning.However due to the stronger intermolecular phase of acid imide
Interaction, having its derivative material, luminous efficiency is lower, and intermolecular aggregation is compared with the defects of strong, dissolubility is poor.And
There is the prominent disadvantage such as permeability difference in preparation-obtained fluorescence sense film, be unfavorable for expansion of the determinand molecule in film
It dissipates, thus sensing capabilities are bad.
Summary of the invention
In order to overcome the disadvantages of the above prior art, the purpose of the present invention is to provide a kind of pair of gas phase acetone and peroxidating
Explosive has the fluorescent chemicals of sensing function and the preparation method and application of fluorescence sense film.
In order to achieve the above object, the present invention is achieved by the following scheme:
The invention discloses the fluorescent chemicals that a kind of pair of gas phase acetone and peroxidating explosive have sensing function, the fluorescence
The structural formula of compound is as follows:
Wherein, n=1~20.
The invention also discloses the above-mentioned fluorescent chemicals for having sensing function to gas phase acetone and peroxidating explosive
Preparation method, comprising the following steps:
1) prepare compound 1
Acid anhydride, alkylamine, acetic acid dihydrate zinc, imidazoles and water are added sequentially in reaction kettle, at 190~200 DEG C
Reaction 24~30 hours, by reaction solution cooled to room temperature, then by reaction solution be poured into water until Precipitation it is complete, take out
Filter, with water and methanol elution, dry, progress pillar layer separation, obtained compound 1；
2) prepare compound 2
Compound 1 is dissolved in methylene chloride, bromine is added into reaction system, is then refluxed for being stirred to react 5~8 small
When, reaction solution rotary evaporation is removed into solvent, carries out pillar layer separation, compound 2 is made；
3) prepare compound 3
Under protection of argon gas, by compound 2, triisopropyl acetenyl silicon, tris(dibenzylideneacetone) dipalladium, three (adjacent first
Base phenyl) phosphorus is placed in Shrek pipe, dry toluene and anhydrous diisopropylamine are added thereto, reaction system is at 65~80 DEG C
Reaction 18~24 hours, then rotary evaporation removes solvent, carries out pillar layer separation, and compound 3 is made；
4) prepare compound 4
Compound 3 is dissolved in anhydrous tetrahydro furan, and being stirred at room temperature dissolves it sufficiently, then thereto by
Be added dropwise to the tetrahydrofuran solution of tetrabutyl ammonium fluoride, room temperature is protected from light that the reaction was continued 3~5 hours, then into reaction system plus
Obtained dried object is carried out pillar layer separation, compound 4 is made by water using filter, drying；
Wherein, the structural formula of the compound 4 are as follows:
Wherein, n is 1~20 in structural formula；
5) prepare compound 5
8-hydroxyquinoline, 4- iodobenzene boric acid, potassium phosphate are dissolved in solvent, it is small that 20~24 are reacted at 100~110 DEG C
When, then rotary evaporation removes solvent, carries out pillar layer separation, obtains greenish yellow solid, i.e. compound 5；
Wherein, the structural formula of the compound 5 are as follows:
6) target product is prepared
Under protection of argon gas, by compound 4, compound 5, tris(dibenzylideneacetone) dipalladium and three (o-methyl-phenyl) phosphorus
It is placed in Shrek pipe, dry toluene is added thereto and anhydrous triethylamine, reaction system react 18~24 at 65~80 DEG C
Hour, then rotary evaporation removes solvent, carries out pillar layer separation, obtains target product and explodes to gas phase acetone and peroxidating
Object has the fluorescent chemicals of sensing function.
Preferably, the consumption proportion of reactant is as follows in each step:
In step 1), the molar ratio to acid anhydride, alkylamine, acetic acid dihydrate zinc, imidazoles and water is 1:(0.5~0.6):
(0.19~0.25): (25~35): (45~55)；
In step 2), the molar ratio of compound 1, bromine and methylene chloride is 1:(2.2~3): (1700~1800)；
In step 3), compound 2, triisopropyl acetenyl silicon, tris(dibenzylideneacetone) dipalladium, three (o-methyl-phenyls)
The molar ratio of phosphorus, dry toluene and anhydrous diisopropylamine is 1:(1.1~1.5): (1.1~1.2): (0.65~0.75): (90
~100): (14~18)；
In step 4), the molar ratio of compound 3, tetrabutyl ammonium fluoride and anhydrous tetrahydro furan is 1:(3~4): (160
~175)；
In step 5), the molar ratio of 8-hydroxyquinoline, 4- iodobenzene boric acid and potassium phosphate is 1:(8.5~9.5): (2.8~
3.2)；
It is compound 5, compound 4, tris(dibenzylideneacetone) dipalladium, three (o-methyl-phenyl) phosphorus, anhydrous in step 6)
The molar ratio of toluene and anhydrous triethylamine is 1:(2.1~2.5): (0.1~0.15): (0.65~0.75): (20~25):
(3.6~5).
Preferably, each step pillar layer separation eluent selection is as follows:
In step 1), pillar layer separation is using methylene chloride as eluent；
In step 2), pillar layer separation is using methylene chloride as eluent；
In step 3), pillar layer separation is using methylene chloride-n-hexane system as eluent, wherein methylene chloride with just
The volume ratio of hexane is 1:1；
In step 4), pillar layer separation is using methylene chloride-n-hexane system as eluent, wherein methylene chloride with just
The volume ratio of hexane is 2:1；
In step 6), carrying out pillar layer separation is using methylene chloride-n-hexane system as eluent, wherein methylene chloride
Volume ratio with n-hexane is 2:1.
Preferably, in step 5), the solvent is Isosorbide-5-Nitrae-dioxane, toluene or n,N-Dimethylformamide.
The invention also discloses use the above-mentioned fluorescence chemical combination for having sensing function to gas phase acetone and peroxidating explosive
The method that object prepares fluorescence sense film, comprising the following steps:
1) fluorescent chemicals for having sensing function to gas phase acetone and peroxidating explosive are taken, it is molten that chloroform is added
Agent, compound concentration are 1 × 10-4~1 × 10-3The stock solution of mol/L stands, is sealed, spare；
2) fluorescent chemicals package assembly made from step 1) is evenly applied in matrix, is placed at room temperature for 1~2 hour,
In vacuum oven, 40~60 DEG C drying 12~24 hours under 3000Pa pressure are taken out, are sealed, and fluorescence sense is made
Film.
Preferably, in step 2), the matrix is silica gel plate matrix, filter paper matrix, glass matrix or macromolecule oil base
Matter；The coating volume is 0.05~0.2 μ L/cm2。
The invention also discloses adopt fluorescence sense film obtained with the aforedescribed process.
The invention also discloses detecting acetone gas and/or peroxidating explosive gas using above-mentioned fluorescence sense film
Application in body.
Preferably, the peroxidating explosive gas is three peroxidating tri acetylacetonates and/or diperoxy diacetone.
Compared with prior art, the invention has the following advantages:
The fluorescent chemicals disclosed by the invention for having sensing function to gas phase acetone and peroxidating explosive are by design
Imide derivative modification four-coordination organic boron quinoline fluorescent chemicals, in the molecular structure of compounds, boron atom
Using classical sp3Hybrid form so that entire molecule displays go out rigidity it is relatively strong, typical positive four with special space structure
Face body configuration can effectively inhibit imido intermolecular stronger interaction, reduce the accumulation of intercellular tight
Effect, greatly increase it is deliquescent make its derivative luminescent material performance enhancement simultaneously, be fluorescence sense film building
It lays a good foundation.
The invention also discloses the above-mentioned fluorescent chemicals for having sensing function to gas phase acetone and peroxidating explosive, i.e.,
The synthetic method of imide modified four-coordination boron quinoline, this method is easy to operate, and raw material is easy to get, and reaction condition is mild,
It is low for equipment requirements, it is suitble to large-scale production.
The invention also discloses based on the above-mentioned fluorescent chemicals for having sensing function to gas phase acetone and peroxidating explosive
The preparation method of the fluorescence sense film of i.e. imide modified four-coordination boron quinoline, this method is easy to operate, controllably
Property it is strong, low in cost, prepared fluorescence sense film photochemistry, thermodynamic stability be good, long service life, is a kind of excellent
Acetone gas at room temperature, peroxidating explosive gas sensing thin film material, efficiently solve acetone gas sensor work
The high problem of temperature.
The present invention by above-mentioned fluorescent chemicals by simple solution self-assembling technique, solution drop coating after being assembled in
Silica matrix surface is prepared with excellent photochemistry, thermodynamic stability, and loose porous fluorescence sense film.
Since the fluorescent chemicals have special nonplanar structure, so that the sense film being prepared has very big specific surface area
And porosity, it is rich in molecular channel, it is ensured that determinand molecule is spread well in film；In addition, the duct pair formed
Biggish help is all had in the promotion of sensing selectivity and sensitivity.Sensing capabilities are studies have shown that the fluorescence sense film exists
Highly sensitive, highly selective response is shown to acetone gas at room temperature, and is responded with turnaround time quickly, sensing process is complete
It is reversible, using the factor of capillary condensation phenomenon and solvation caused by nonplanar structure, eliminate the dry of common interference object
It disturbs, practicability is high.This kind of film and Commercial optical instrument are used in combination to the Sensitive Detection that acetone gas may be implemented.This
Outside, by sense film device, acetone gas special detector can also be developed.Finally, testing sense film to peroxide
The response for changing explosive TATP and DADP, shows excellent sensing capabilities.
Detailed description of the invention
Fig. 1 is the high resolution mass spectrum figure of target fluorescent compound produced by the present invention；
Fig. 2 is the nucleus magnetic hydrogen spectrum figure of target fluorescent compound produced by the present invention；
Fig. 3 is the nuclear-magnetism carbon spectrogram of target fluorescent compound produced by the present invention；
Fig. 4 is the nuclear-magnetism boron spectrogram of target fluorescent compound produced by the present invention；
Fig. 5 is the excitation-emission spectrogram of fluorescence sense film produced by the present invention；
Fig. 6 is the obtained fluorescence sense film photochemical stability monitoring figure of the present invention；
Fig. 7 is fluorescence sense film thermodynamic stability produced by the present invention monitoring figure；
Fig. 8 is that fluorescence sense film produced by the present invention responds the gas phase fluorescence sense of acetone and common interference object
Figure；
Fig. 9 is response sensitivity test chart of the fluorescence sense film produced by the present invention to acetone gas；
Figure 10 is recovery test chart of the fluorescence sense film produced by the present invention to acetone gas；
Figure 11 is the long-time stability test chart that fluorescence sense film produced by the present invention responds acetone gas.
Figure 12 be fluorescence sense film produced by the present invention to three peroxidating tri acetylacetonate (a) of peroxidating explosive gas and
Diperoxy diacetone (b) sensing testing figure.
Specific embodiment
In order to enable those skilled in the art to better understand the solution of the present invention, below in conjunction in the embodiment of the present invention
Attached drawing, technical scheme in the embodiment of the invention is clearly and completely described, it is clear that described embodiment is only
The embodiment of a part of the invention, instead of all the embodiments.Based on the embodiments of the present invention, ordinary skill people
The model that the present invention protects all should belong in member's every other embodiment obtained without making creative work
It encloses.
In addition, term " includes " and " having " and their any deformation, it is intended that covering non-exclusive includes example
Such as, the process, method, system, product or equipment for containing a series of steps or units those of are not necessarily limited to be clearly listed
Step or unit, but may include being not clearly listed or intrinsic for these process, methods, product or equipment other
Step or unit.
The invention will be described in further detail with reference to the accompanying drawing:
Embodiment 1
The preparation of target fluorescent compound (in the present embodiment, n=7, raw material chooses octodrine)
1. synthesizing compound 1
16.5g acid anhydride, 3.8mL octodrine, 2.0g acetic acid dihydrate zinc, 85g imidazoles and 36mL water are added sequentially to
In 200mL reaction kettle, reaction system is heated to 190 DEG C, stirs lower reaction 24 hours, by reaction solution cooled to room temperature,
Then reaction solution is poured into a large amount of water, a large amount of precipitatings are precipitated, filter, is eluted with water and methanol, is dry, being to wash with methylene chloride
De- liquid carries out pillar layer separation, and peony compound 1 is made；
Its reaction equation is as follows:
2. synthesizing compound 2
0.636g compound 1 is weighed in 250mL single port bottle, be added 165mL methylene chloride stirring and dissolving, with syringe to
0.19mL bromine is added in reaction system, is then heated to 45 DEG C, return stirring reacts 5 hours, rotates reaction solution steam later
Hair removes solvent, carries out pillar layer separation by eluent of methylene chloride, orange red compound 2 is made；
Its reaction equation is as follows:
3. synthesizing compound 3
Under protection of argon gas, it is (adjacent that 511mg compound 2,91.5mg tris(dibenzylideneacetone) dipalladium, 236 mg tri- are weighed
Aminomethyl phenyl) in 35mL Shrek pipe, 10mL dry toluene and the anhydrous diisopropylamine of 2mL is added in phosphorus thereto, then with injecting
0.25mL triisopropyl acetenyl silicon is added in device, and reaction system is stirred to react 18 hours at 65 DEG C, cooled to room temperature, so
After rotate evaporation of solvent, using methylene chloride: n-hexane=1:1 system as eluent carry out pillar layer separation, be made dark red
Color compound 3；
Its reaction equation is as follows:
4. synthesizing compound 4
150mg compound 3 is weighed in 10mL single port bottle, 4mL anhydrous tetrahydro furan is added, and be stirred at room temperature 5 points
Clock dissolves it sufficiently, adds the tetrahydrofuran solution of the 1mol/L of 0.732mL tetrabutyl ammonium fluoride, it is anti-that room temperature is protected from light continuation
It answers 3 hours, suitable quantity of water is added thereto, filtering, drying, by obtained dried object methylene chloride: n-hexane=2:1 system is
Eluant, eluent carries out pillar layer separation, and peony compound 4 is made；
Its reaction equation is as follows:
5. synthesizing compound 5
0.1452g 8-hydroxyquinoline, 2.2316g 4- iodobenzene boric acid, 0.6368g potassium phosphate are weighed in 100mL single port bottle
In, the anhydrous Isosorbide-5-Nitrae-dioxane of 50mL is added, temperature of reaction system is risen to 100 DEG C, is stirred to react 20 hours, then rotation is steamed
Hair removes solvent, is that eluent carries out pillar layer separation with methylene chloride, obtains greenish yellow solid, i.e. compound 5；
Its reaction equation is as follows:
6. synthesizing target fluorescent compound
Under protection of argon gas, weigh 36mg compound 4,20mg compound 5,3.37mg tris(dibenzylideneacetone) dipalladium,
2.5mL dry toluene and anhydrous three second of 0.5mL is added in 15mL Shrek pipe in (o-methyl-phenyl) phosphorus of 6.9mg tri- thereto
Amine, reaction system react 18 hours at 65 DEG C, and then rotary evaporation removes solvent, with methylene chloride: n-hexane=2:1 system
Pillar layer separation is carried out for eluent, target fluorescent compound is obtained, i.e., has sensing to gas phase acetone and peroxidating explosive
The fluorescent chemicals of function；
Its reaction equation is as follows:
Structural characterization data result through target fluorescent compound produced by the present invention is as shown in Figs 1-4.
Embodiment 2
The preparation (n=3 in the present embodiment) of target fluorescent compound
1. synthesizing compound 1
16.5g acid anhydride, 2.3mL butylamine, 2.0g acetic acid dihydrate zinc, 85g imidazoles and 36mL water are added sequentially to 200mL
In reaction kettle, reaction system is heated to 190 DEG C, stirs lower reaction 24 hours, reaction solution cooled to room temperature then will
Reaction solution pours into a large amount of water, and a large amount of precipitatings are precipitated, filter, with water and methanol elution, dry, using methylene chloride as eluent into
Peony compound 1 is made in row pillar layer separation；
Its reaction equation is as follows:
2. synthesizing compound 2
0.554g compound 1 is weighed in 250mL single port bottle, be added 165mL methylene chloride stirring and dissolving, with syringe to
0.19mL bromine is added in reaction system, is then heated to 45 DEG C, return stirring reacts 5 hours, rotates reaction solution steam later
Hair removes solvent, carries out pillar layer separation by eluent of methylene chloride, orange red compound 2 is made；
Its reaction equation is as follows:
3. synthesizing compound 3
Under protection of argon gas, it is (adjacent that 455mg compound 2,91.5mg tris(dibenzylideneacetone) dipalladium, 236 mg tri- are weighed
Aminomethyl phenyl) in 35mL Shrek pipe, 10mL dry toluene and the anhydrous diisopropylamine of 2mL is added in phosphorus thereto, then with injecting
0.25mL triisopropyl acetenyl silicon is added in device, and reaction system is stirred to react 18 hours at 65 DEG C, cooled to room temperature, so
After rotate evaporation of solvent, using methylene chloride: n-hexane=1:1 system as eluent carry out pillar layer separation, be made dark red
Color compound 3；
Its reaction equation is as follows:
4. synthesizing compound 4
136mg compound 3 is weighed in 10mL single port bottle, 4mL anhydrous tetrahydro furan is added, and be stirred at room temperature 5 points
Clock dissolves it sufficiently, adds the tetrahydrofuran solution of the 1mol/L of 0.732mL tetrabutyl ammonium fluoride, it is anti-that room temperature is protected from light continuation
It answers 3 hours, suitable quantity of water is added thereto, filtering, drying, by obtained dried object methylene chloride: n-hexane=2:1 system is
Eluant, eluent carries out pillar layer separation, and peony compound 4 is made；
Its reaction equation is as follows:
5. synthesizing compound 5
0.1452g 8-hydroxyquinoline, 2.2316g 4- iodobenzene boric acid, 0.6368g potassium phosphate are weighed in 100mL single port bottle
In, the anhydrous Isosorbide-5-Nitrae-dioxane of 50mL is added, temperature of reaction system is risen to 100 DEG C, is stirred to react 20 hours, then rotation is steamed
Hair removes solvent, is that eluent carries out pillar layer separation with methylene chloride, obtains greenish yellow solid, i.e. compound 5；
Its reaction equation is as follows:
6. synthesizing compound 6
Under protection of argon gas, weigh 32mg compound 4,20mg compound 5,3.37mg tris(dibenzylideneacetone) dipalladium,
2.5mL dry toluene and anhydrous three second of 0.5mL is added in 15mL Shrek pipe in (o-methyl-phenyl) phosphorus of 6.9mg tri- thereto
Amine, reaction system react 18 hours at 65 DEG C, and then rotary evaporation removes solvent, with methylene chloride: n-hexane=2:1 system
Pillar layer separation is carried out for eluent, target fluorescent compound is obtained, i.e., has sensing to gas phase acetone and peroxidating explosive
The fluorescent chemicals of function；
Its reaction equation is as follows:
Embodiment 3
The preparation (n=5 in the present embodiment) of target fluorescent compound
1. synthesizing compound 1
By 16.5g acid anhydride, 3.1mL, amine, 2.0g acetic acid dihydrate zinc, 85g imidazoles and 36mL water are added sequentially to 200mL
In reaction kettle, reaction system is heated to 190 DEG C, stirs lower reaction 24 hours, reaction solution cooled to room temperature then will
Reaction solution pours into a large amount of water, and a large amount of precipitatings are precipitated, filter, with water and methanol elution, dry, using methylene chloride as eluent into
Peony compound 1 is made in row pillar layer separation；
Its reaction equation is as follows:
2. synthesizing compound 2
0.594g compound 1 is weighed in 250mL single port bottle, be added 165mL methylene chloride stirring and dissolving, with syringe to
0.19mL bromine is added in reaction system, is then heated to 45 DEG C, return stirring reacts 5 hours, rotates reaction solution steam later
Hair removes solvent, carries out pillar layer separation by eluent of methylene chloride, orange red compound 2 is made；Its reaction equation is such as
Under:
3. synthesizing compound 3
Under protection of argon gas, it is (adjacent that 484mg compound 2,91.5mg tris(dibenzylideneacetone) dipalladium, 236 mg tri- are weighed
Aminomethyl phenyl) in 35mL Shrek pipe, 10mL dry toluene and the anhydrous diisopropylamine of 2mL is added in phosphorus thereto, then with injecting
0.25mL triisopropyl acetenyl silicon is added in device, and reaction system is stirred to react 18 hours at 65 DEG C, cooled to room temperature, so
After rotate evaporation of solvent, using methylene chloride: n-hexane=1:1 system as eluent carry out pillar layer separation, be made dark red
Color compound 3；
Its reaction equation is as follows:
4. synthesizing compound 4
142mg compound 3 is weighed in 10mL single port bottle, 4mL anhydrous tetrahydro furan is added, and be stirred at room temperature 5 points
Clock dissolves it sufficiently, adds the tetrahydrofuran solution of the 1mol/L of 0.732mL tetrabutyl ammonium fluoride, it is anti-that room temperature is protected from light continuation
It answers 3 hours, suitable quantity of water is added thereto, filtering, drying, by obtained dried object methylene chloride: n-hexane=2:1 system is
Eluant, eluent carries out pillar layer separation, and peony compound 4 is made；
Its reaction equation is as follows:
5. synthesizing compound 5
0.1452g 8-hydroxyquinoline, 2.2316g 4- iodobenzene boric acid, 0.6368g potassium phosphate are weighed in 100mL single port bottle
In, the anhydrous Isosorbide-5-Nitrae-dioxane of 50mL is added, temperature of reaction system is risen to 100 DEG C, is stirred to react 20 hours, then rotation is steamed
Hair removes solvent, is that eluent carries out pillar layer separation with methylene chloride, obtains greenish yellow solid, i.e. compound 5；
Its reaction equation is as follows:
6. synthesizing target fluorescent compound
Under protection of argon gas, weigh 34mg compound 4,20mg compound 5,3.37mg tris(dibenzylideneacetone) dipalladium,
2.5mL dry toluene and anhydrous three second of 0.5mL is added in 15mL Shrek pipe in (o-methyl-phenyl) phosphorus of 6.9mg tri- thereto
Amine, reaction system react 18 hours at 65 DEG C, and then rotary evaporation removes solvent, with methylene chloride: n-hexane=2:1 system
Pillar layer separation is carried out for eluent, target fluorescent compound is obtained, i.e., has sensing to gas phase acetone and peroxidating explosive
The fluorescent chemicals of function；
Its reaction equation is as follows:
Embodiment 4
The preparation (n=15 in the present embodiment) of target fluorescent compound
1. synthesizing compound 1
16.5g acid anhydride, 6.8mL cetylamine, 2.0g acetic acid dihydrate zinc, 85g imidazoles and 36mL water are added sequentially to
In 200mL reaction kettle, reaction system is heated to 190 DEG C, stirs lower reaction 24 hours, by reaction solution cooled to room temperature,
Then reaction solution is poured into a large amount of water, a large amount of precipitatings are precipitated, filter, is eluted with water and methanol, is dry, being to wash with methylene chloride
De- liquid carries out pillar layer separation, and peony compound 1 is made；
Its reaction equation is as follows:
2. synthesizing compound 2
0.801g compound 1 is weighed in 250mL single port bottle, be added 165mL methylene chloride stirring and dissolving, with syringe to
0.19mL bromine is added in reaction system, is then heated to 45 DEG C, return stirring reacts 5 hours, rotates reaction solution steam later
Hair removes solvent, carries out pillar layer separation by eluent of methylene chloride, orange red compound 2 is made；
Its reaction equation is as follows:
3. synthesizing compound 3
Under protection of argon gas, it is (adjacent that 624mg compound 2,91.5mg tris(dibenzylideneacetone) dipalladium, 236 mg tri- are weighed
Aminomethyl phenyl) in 35mL Shrek pipe, 10mL dry toluene and the anhydrous diisopropylamine of 2mL is added in phosphorus thereto, then with injecting
0.25mL triisopropyl acetenyl silicon is added in device, and reaction system is stirred to react 18 hours at 65 DEG C, cooled to room temperature, so
After rotate evaporation of solvent, using methylene chloride: n-hexane=1:1 system as eluent carry out pillar layer separation, be made dark red
Color compound 3；
Its reaction equation is as follows:
4. synthesizing compound 4
177mg compound 3 is weighed in 10mL single port bottle, 4mL anhydrous tetrahydro furan is added, and be stirred at room temperature 5 points
Clock dissolves it sufficiently, adds the tetrahydrofuran solution of the 1mol/L of 0.732mL tetrabutyl ammonium fluoride, it is anti-that room temperature is protected from light continuation
It answers 3 hours, suitable quantity of water is added thereto, filtering, drying, by obtained dried object methylene chloride: n-hexane=2:1 system is
Eluant, eluent carries out pillar layer separation, and peony compound 4 is made；
Its reaction equation is as follows:
5. synthesizing compound 5
0.1452g 8-hydroxyquinoline, 2.2316g 4- iodobenzene boric acid, 0.6368g potassium phosphate are weighed in 100mL single port bottle
In, the anhydrous Isosorbide-5-Nitrae-dioxane of 50mL is added, temperature of reaction system is risen to 100 DEG C, is stirred to react 20 hours, then rotation is steamed
Hair removes solvent, is that eluent carries out pillar layer separation with methylene chloride, obtains greenish yellow solid, i.e. compound 5；
Its reaction equation is as follows:
6. synthesizing compound 6
Under protection of argon gas, weigh 45mg compound 4,20mg compound 5,3.37mg tris(dibenzylideneacetone) dipalladium,
2.5mL dry toluene and anhydrous three second of 0.5mL is added in 15mL Shrek pipe in (o-methyl-phenyl) phosphorus of 6.9mg tri- thereto
Amine, reaction system react 18 hours at 65 DEG C, and then rotary evaporation removes solvent, with methylene chloride: n-hexane=2:1 system
Pillar layer separation is carried out for eluent, target fluorescent compound is obtained, i.e., has sensing to gas phase acetone and peroxidating explosive
The fluorescent chemicals of function；
Its reaction equation is as follows:
Embodiment 5
In the synthesis for preparing imide modified four-coordination boron quinoline fluorescent chemicals step (5) of Examples 1 to 4
It closes in object 5, Isosorbide-5-Nitrae-dioxane used is replaced with isometric toluene, other steps of the embodiment and corresponding embodiment phase
Together, prepare compound 5, other steps are identical as Examples 1 to 4.
Embodiment 6
In the synthesis for preparing imide modified four-coordination boron quinoline fluorescent chemicals step (5) of Examples 1 to 4
Close in object 5, Isosorbide-5-Nitrae-dioxane used is replaced with isometric n,N-Dimethylformamide, other steps of the embodiment and
Corresponding embodiment is identical, prepare compound 5, other steps are identical as Examples 1 to 4.
Using target fluorescent compound made from above-described embodiment, i.e., there is sensing function to gas phase acetone and peroxidating explosive
The method that the fluorescent chemicals of energy prepare fluorescence sense film, comprising the following steps:
1) by target fluorescent compound solvent chloroform, compound concentration is 1 × 10-4~1 × 10-3Mol/L's is molten
Liquid stands the stock solution, to obtain the package assembly of fluorescent chemicals, is sealed, spare；
2) above-mentioned stock solution is evenly applied in clean silica gel plate matrix, coating volume is 0.05~0.2 μ L/
cm2, it is placed at room temperature for 1 hour, in vacuum oven, lower 50 DEG C of 3000Pa pressure are dried in vacuo 12 hours, are taken out, sealing is protected
It deposits, fluorescence sense film is prepared.
In order to verify effect of the invention, to synthesized based on acid imide four-coordination boron quinoline fluorescence in embodiment 1
The fluorescence sense film of compound has carried out a large amount of laboratory research experiment, and various experimental conditions are as follows:
1, basic Fluorescence behaviour characterization
Prepared fluorescence sense film is excited using 920 single photon counting Fluorescence Spectrometer of Edinburg instrument FLS
The characterization of emission spectrum, is as a result shown in Fig. 5.As shown in Figure 5, the maximum excitation wavelength of the fluorescence sense film be 400nm and
500nm, maximum emission wavelength are 500nm and 590nm, provide light source and Detection wavelength information for the building of fluorescent optical sensor.
Distinguishingly, we select 400nm as excitation light source, the fluorescence intensity at 590nm.
2, photochemistry and the thermodynamic stability test of fluorescence membrane
Photobleaching is an extremely important phenomenon for limiting fluorescence membrane sensor and obtaining practical application, therefore will be thin
Film is used for before fluorescence detection, is very important to the research of its photochemical stability and thermodynamic stability.Dependence test
As a result as shown in Figure 6 and Figure 7.Test result show prepared film by continuous 28 hours light irradiation after, fluorescence
Intensity there is no variation, shows it with excellent photochemical stability substantially；Moreover, in air expose six months with
On, fluorescence color and intensity also there is no and changes, it was demonstrated that it is with preferable thermodynamic stability, result above
The nonplanar structure of four-coordination boron compound is had benefited from, this is also that solid foundation has been established in the research of sensing behavior.
3, fluorescence membrane tests the detection of acetone and peroxidating explosive steam
It is measured using actual sample of the fluorescence sense detection platform to fluorescence sense film of the present invention.Wherein, wait divide
Analysis sample is acetone steam, peroxidating explosive steam, and chaff interferent chooses relatively conventional organic solvent (tetrahydrofuran, benzene, first
Benzene, methylene chloride, chloroform, dioxane, pentane, n-hexane, normal heptane, methanol), hydrogen peroxide, common explosive
(TNT, DNT, HMX, RDX, picric acid), water and its aqueous bath accessory (shampoo, hair conditioner, hand lotion, perfume etc.), milk
Oil, soiled clothes, fruit (apple, pears, banana) and air.
Operating process are as follows:
1) a small amount of different sample to be analysed are packaged in 4L Brown Glass Brown glass bottles and jars only, are stood overnight under room temperature state, for use；
2) fluorescence sense film is placed in detecting instrument, and tests 28 kinds of analysans respectively at room temperature；
3) analysans is tested, and using microsyringe sample introduction, the bottleneck with 100mL glass syringe in step 1) is drawn
The analyte gas of certain volume, and glass syringe is placed at instrument bleeding point, sample injection time is about 1~3 second, sample introduction speed
Degree is 1mL/s, after replying, repeats above-mentioned test.
4) determinand of various concentration is taken is obtained with the method for Dilution air response multiple.
Its test result is as illustrated in figs. 8-11.
By the test result of Fig. 8 it will be seen that the film is fluorescent quenching type to the response of acetone, and common have
Solvent shows a degree of sensitized fluorescence, and water, common explosive, bath accessory and fruit are strong to the fluorescence of film
Degree does not influence substantially, thus can illustrate, film shows excellent sensing selectivity to acetone steam, practical answers for its
With laying a good foundation.
Fig. 9 is sensitivity determination figure of the fluorescence sense film to acetone steam.From test result it will be seen that with
The fluorescence intensity of the increase of acetone steam concentration, film is significantly quenched.Acetone steam concentration be 50 ppm when, still have compared with
The fluorescent quenching of big degree, thus alternatively its bright sensing sensitivity is lower than 50ppm.
Figure 10 is that fluorescence sense film responds recovery to acetone steam and senses the test chart of speed.As seen from the figure, exist
After METHOD FOR CONTINUOUS DETERMINATION 60 times, the response curve measuring with first time is still shown, thus shows excellent reply
Property；Meanwhile response speed is lower than 1s, replys speed and is less than 10s, and sensing process completely reversibility, thus have realize completely
A possibility that practical application.
Figure 11 is measurement chart of the fluorescence sense film to acetone steam response for a long time.30 days continuous (interval two days) is to third
After ketone steam is tested, sensing capabilities there is no variation, illustrate that it shows excellent stability, obtain for it substantially
It obtains practical application and has laid sturdy basis.
Figure 12 is response measurement chart of the fluorescence sense film to peroxidating explosive (TATP and DADP).As seen from the figure, with
The increase of peroxidating explosion object amount, the fluorescence intensity generation of film significantly become smaller, thus the inspection to the substance may be implemented
It surveys, provides possibility for its practical application.
In conclusion the organic boron derivative of four-coordination with nonplanar structure is introduced into setting for fluorescence sense by the present invention
Meter, the molecular channel formed after being accumulated on a molecular scale using nonplanar structure, using the phenomenon that capillary condensation and
Solvation realizes acetone steam, the sensitive, highly selective of peroxidating explosive steam, recovery and stabilization at room temperature
Property recognition detection, solve the problems, such as that operating temperature is high and glimmering to have excellent performance when previous methods existing detection substantially
The design of light sensing film provides new thinking.
Herein on basis, propose new for more difficult detection substance-peroxidating explosive (TATP/DADP) sensing
Strategy is realized and is answered the initiative of peroxidating explosive gas phase sensing that is, by the sensing to its room-temperature decomposition product acetone
With.Substantially solve the problems, such as that operating temperature is high when detection existing for previous methods, and thin for the fluorescence sense haveing excellent performance
The design of film provides new thinking.
Preparation method of the present invention is easy to operate, reaction condition is mild, and prepared fluorescent chemicals photochemistry, thermodynamics are steady
Fluorescence sense film high sensitivity, the good, long service life of selectivity qualitative good, obtain, are that a kind of excellent fluorescence sense is thin
The sensitive inspection that may be implemented to acetone steam and peroxidating explosive is used in combination in this kind of film and Commercial optical instrument by film
It surveys.In addition, acetone gas, peroxidating explosive gas specific detector can also be developed by sense film device.
The above content is merely illustrative of the invention's technical idea, and this does not limit the scope of protection of the present invention, all to press
According to technical idea proposed by the present invention, any changes made on the basis of the technical scheme each falls within claims of the present invention
Protection scope within.
Claims (10)
1. the fluorescent chemicals that a kind of pair of gas phase acetone and peroxidating explosive have sensing function, which is characterized in that this is Fluoresceinated
The structural formula for closing object is as follows:
Wherein, n=1~20.
2. the preparation side of the fluorescent chemicals described in claim 1 for having sensing function to gas phase acetone and peroxidating explosive
Method, which comprises the following steps:
1) prepare compound 1
Acid anhydride, alkylamine, acetic acid dihydrate zinc, imidazoles and water are added sequentially in reaction kettle, reacted at 190~200 DEG C
24~30 hours, by reaction solution cooled to room temperature, then by reaction solution be poured into water until Precipitation it is complete, filter,
With water and methanol elution, dry, progress pillar layer separation, obtained compound 1；
2) prepare compound 2
Compound 1 is dissolved in methylene chloride, bromine is added into reaction system, is then refluxed for being stirred to react 5~8 hours, it will
Reaction solution rotary evaporation removes solvent, carries out pillar layer separation, and compound 2 is made；
3) prepare compound 3
Under protection of argon gas, by compound 2, triisopropyl acetenyl silicon, tris(dibenzylideneacetone) dipalladium, three (o-methyl-benzenes
Base) phosphorus is placed in Shrek pipe, and dry toluene is added thereto and anhydrous diisopropylamine, reaction system are reacted at 65~80 DEG C
18~24 hours, then rotary evaporation removed solvent, carried out pillar layer separation, and compound 3 is made；
4) prepare compound 4
Compound 3 is dissolved in anhydrous tetrahydro furan, and being stirred at room temperature dissolves it sufficiently, is then added dropwise thereto
Entering the tetrahydrofuran solution of tetrabutyl ammonium fluoride, room temperature is protected from light that the reaction was continued 3~5 hours, then into reaction system plus water, then
It filtered, dried, obtained dried object is subjected to pillar layer separation, compound 4 is made；
Wherein, the structural formula of the compound 4 are as follows:
Wherein, n is 1~20 in structural formula；
5) prepare compound 5
8-hydroxyquinoline, 4- iodobenzene boric acid, potassium phosphate are dissolved in solvent, react 20~24 hours at 100~110 DEG C, so
After rotate evaporation of solvent, carry out pillar layer separation, obtain greenish yellow solid, i.e. compound 5；
Wherein, the structural formula of the compound 5 are as follows:
6) target product is prepared
Under protection of argon gas, compound 4, compound 5, tris(dibenzylideneacetone) dipalladium and three (o-methyl-phenyl) phosphorus are placed in
In Shrek pipe, dry toluene is added thereto and anhydrous triethylamine, reaction system are reacted 18~24 hours at 65~80 DEG C,
Then rotary evaporation removes solvent, carries out pillar layer separation, obtaining target product has gas phase acetone and peroxidating explosive
The fluorescent chemicals of sensing function.
3. the preparation of the fluorescent chemicals according to claim 2 for having sensing function to gas phase acetone and peroxidating explosive
Method, which is characterized in that the consumption proportion of reactant is as follows in each step:
In step 1), the molar ratio to acid anhydride, alkylamine, acetic acid dihydrate zinc, imidazoles and water is 1:(0.5~0.6): (0.19
~0.25): (25~35): (45~55)；
In step 2), the molar ratio of compound 1, bromine and methylene chloride is 1:(2.2~3): (1700~1800)；
In step 3), compound 2, triisopropyl acetenyl silicon, tris(dibenzylideneacetone) dipalladium, three (o-methyl-phenyl) phosphorus,
The molar ratio of dry toluene and anhydrous diisopropylamine is 1:(1.1~1.5): (1.1~1.2): (0.65~0.75): (90~
100): (14~18)；
In step 4), the molar ratio of compound 3, tetrabutyl ammonium fluoride and anhydrous tetrahydro furan is 1:(3~4): (160~
175)；
In step 5), the molar ratio of 8-hydroxyquinoline, 4- iodobenzene boric acid and potassium phosphate is 1:(8.5~9.5): (2.8~3.2)；
In step 6), compound 5, compound 4, tris(dibenzylideneacetone) dipalladium, three (o-methyl-phenyl) phosphorus, dry toluene and
The molar ratio of anhydrous triethylamine is 1:(2.1~2.5): (0.1~0.15): (0.65~0.75): (20~25): (3.6~5).
4. the preparation of the fluorescent chemicals according to claim 2 for having sensing function to gas phase acetone and peroxidating explosive
Method, which is characterized in that each step pillar layer separation eluent selection is as follows:
In step 1), pillar layer separation is using methylene chloride as eluent；
In step 2), pillar layer separation is using methylene chloride as eluent；
In step 3), pillar layer separation is using methylene chloride-n-hexane system as eluent, wherein methylene chloride and n-hexane
Volume ratio be 1:1；
In step 4), pillar layer separation is using methylene chloride-n-hexane system as eluent, wherein methylene chloride and n-hexane
Volume ratio be 2:1；
In step 6), carry out pillar layer separation be using methylene chloride-n-hexane system as eluent, wherein methylene chloride with just
The volume ratio of hexane is 2:1.
5. the preparation of the fluorescent chemicals according to claim 2 for having sensing function to gas phase acetone and peroxidating explosive
Method, which is characterized in that in step 5), the solvent is Isosorbide-5-Nitrae-dioxane, toluene or n,N-Dimethylformamide.
6. being prepared using the fluorescent chemicals described in claim 1 for having sensing function to gas phase acetone and peroxidating explosive glimmering
The method of light sensing film, which comprises the following steps:
1) fluorescent chemicals for having sensing function to gas phase acetone and peroxidating explosive are taken, chloroform solvent is added,
Compound concentration is 1 × 10-4~1 × 10-3The stock solution of mol/L stands, is sealed, spare；
2) fluorescent chemicals package assembly made from step 1) is evenly applied in matrix, 1~2 hour is placed at room temperature for, true
In empty drying box, 40~60 DEG C drying 12~24 hours under 3000Pa pressure are taken out, are sealed, and fluorescence sense film is made.
7. the method according to claim 6 for preparing fluorescence sense film, which is characterized in that in step 2), the matrix
For silica gel plate matrix, filter paper matrix, glass matrix or macromolecule oleaginous bases；The coating volume is 0.05~0.2 μ L/cm2。
8. using fluorescence sense film made from method described in claim 6 or 7.
9. application of the fluorescence sense film according to any one of claims 8 in detection acetone gas and/or peroxidating explosive gas.
10. application as claimed in claim 9, which is characterized in that the peroxidating explosive gas is three peroxidating tri acetylacetonates
And/or diperoxy diacetone.
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| CN106317383A (en) * | 2016-08-15 | 2017-01-11 | 陕西师范大学 | Organic monomer containing 8-hydroxyquinoline boron, conjugated polymer based on monomer, preparation method and application |
| CN107698614A (en) * | 2017-08-29 | 2018-02-16 | 陕西师范大学 | A kind of carborane diimide derivative and synthetic method and the sensor array based on it and preparation method and application |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106317383A (en) * | 2016-08-15 | 2017-01-11 | 陕西师范大学 | Organic monomer containing 8-hydroxyquinoline boron, conjugated polymer based on monomer, preparation method and application |
| CN107698614A (en) * | 2017-08-29 | 2018-02-16 | 陕西师范大学 | A kind of carborane diimide derivative and synthetic method and the sensor array based on it and preparation method and application |
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| TOKORO, YUICHIRO ET AL: "Synthesis of Organoboron Quinoline-8-thiolate and Quinoline-8-selenolate Complexes and Their Incorporation into the π-Conjugated Polymer Main-Chain", 《MACROMOLECULES》 * |
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