CN105837492B - A kind of cyanide ion probe, preparation and application - Google Patents
A kind of cyanide ion probe, preparation and application Download PDFInfo
- Publication number
- CN105837492B CN105837492B CN201610186488.0A CN201610186488A CN105837492B CN 105837492 B CN105837492 B CN 105837492B CN 201610186488 A CN201610186488 A CN 201610186488A CN 105837492 B CN105837492 B CN 105837492B
- Authority
- CN
- China
- Prior art keywords
- probe
- cyanide ion
- ion
- detection
- cyanide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000000523 sample Substances 0.000 title claims abstract description 86
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 title claims abstract description 75
- 238000002360 preparation method Methods 0.000 title claims description 5
- 230000000694 effects Effects 0.000 claims abstract description 24
- 238000001514 detection method Methods 0.000 claims abstract description 23
- 230000004044 response Effects 0.000 claims abstract description 15
- 238000012544 monitoring process Methods 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000011630 iodine Substances 0.000 claims abstract description 9
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 9
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 9
- 239000012736 aqueous medium Substances 0.000 claims abstract description 6
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000006069 Suzuki reaction reaction Methods 0.000 claims abstract description 3
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims description 22
- 230000002776 aggregation Effects 0.000 claims description 11
- 238000004220 aggregation Methods 0.000 claims description 11
- 150000002500 ions Chemical class 0.000 claims description 11
- 230000007246 mechanism Effects 0.000 claims description 9
- -1 4- (N, N- dimethylamino) phenyl pinacols borate Chemical class 0.000 claims description 7
- YQSJBGIEKSHMDX-UHFFFAOYSA-N 1,2,2,3-tetramethyl-3h-indole Chemical class C1=CC=C2N(C)C(C)(C)C(C)C2=C1 YQSJBGIEKSHMDX-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 18
- 150000001450 anions Chemical class 0.000 abstract description 9
- 239000000047 product Substances 0.000 abstract description 6
- 229910019142 PO4 Inorganic materials 0.000 abstract description 5
- 239000003651 drinking water Substances 0.000 abstract description 5
- 235000020188 drinking water Nutrition 0.000 abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 5
- 239000003814 drug Substances 0.000 abstract description 4
- 239000010452 phosphate Substances 0.000 abstract description 4
- YNMGRZLDRLHRTN-UHFFFAOYSA-N 1,2,3,3-tetramethyl-2h-indole Chemical class C1=CC=C2C(C)(C)C(C)N(C)C2=C1 YNMGRZLDRLHRTN-UHFFFAOYSA-N 0.000 abstract description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract description 2
- 239000000975 dye Substances 0.000 abstract description 2
- 238000000034 method Methods 0.000 abstract description 2
- YOPXDLOJIFWJLS-UHFFFAOYSA-N B(O)(O)O.C1(=CC=CC=C1)CC(O)(C)C(C)(C)O Chemical compound B(O)(O)O.C1(=CC=CC=C1)CC(O)(C)C(C)(C)O YOPXDLOJIFWJLS-UHFFFAOYSA-N 0.000 abstract 1
- UUKFMAJOKYEWRC-UHFFFAOYSA-N N1=CC=CC2=CC=CC=C12.CC1(CN(C2=CC=CC=C12)C)C Chemical compound N1=CC=CC2=CC=CC=C12.CC1(CN(C2=CC=CC=C12)C)C UUKFMAJOKYEWRC-UHFFFAOYSA-N 0.000 abstract 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 8
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- 239000011591 potassium Substances 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 230000036541 health Effects 0.000 description 4
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 4
- 239000010453 quartz Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 150000002476 indolines Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000005311 nuclear magnetism Effects 0.000 description 3
- 230000008520 organization Effects 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241001269238 Data Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000007836 KH2PO4 Substances 0.000 description 2
- 239000007832 Na2SO4 Substances 0.000 description 2
- 241000736199 Paeonia Species 0.000 description 2
- 235000006484 Paeonia officinalis Nutrition 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 2
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 2
- VDQVEACBQKUUSU-UHFFFAOYSA-M disodium;sulfanide Chemical compound [Na+].[Na+].[SH-] VDQVEACBQKUUSU-UHFFFAOYSA-M 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 2
- 239000011698 potassium fluoride Substances 0.000 description 2
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Substances [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 2
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 2
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 2
- 229910001488 sodium perchlorate Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 229910052979 sodium sulfide Inorganic materials 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 2
- MLZACLPQYBWABT-UHFFFAOYSA-N CNC1=C(C=CC=C1)OB(O)O Chemical compound CNC1=C(C=CC=C1)OB(O)O MLZACLPQYBWABT-UHFFFAOYSA-N 0.000 description 1
- 102000000634 Cytochrome c oxidase subunit IV Human genes 0.000 description 1
- 108050008072 Cytochrome c oxidase subunit IV Proteins 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 235000006508 Nelumbo nucifera Nutrition 0.000 description 1
- 240000002853 Nelumbo nucifera Species 0.000 description 1
- 235000006510 Nelumbo pentapetala Nutrition 0.000 description 1
- 208000003443 Unconsciousness Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910001914 chlorine tetroxide Inorganic materials 0.000 description 1
- 230000001427 coherent effect Effects 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 150000002012 dioxanes Chemical class 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000002384 drinking water standard Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001917 fluorescence detection Methods 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 238000005272 metallurgy Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 231100000668 minimum lethal dose Toxicity 0.000 description 1
- 210000003470 mitochondria Anatomy 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- NKCCODPFBDGPRJ-UHFFFAOYSA-N nitridocarbon(1+) Chemical compound N#[C+] NKCCODPFBDGPRJ-UHFFFAOYSA-N 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000002352 surface water Substances 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- 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
-
- 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
-
- 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
- G01N2021/6417—Spectrofluorimetric devices
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
The invention discloses a kind of cyanide ion probe, that is (E) [2 ˊ (4 N, N dimethylamino phenyls) vinyl] 1,3,3 tri-methyl indole quinoline salt compounded of iodine, it be by o-bromobenzaldehye first with 4 (N, N dimethylaminos) Suzuki reactions occur for phenyl pinacol borate, and gained intermediate is then again with 1,2,3,3 tetramethyl indoline salt compounded of iodine occur Witting reactions and obtained.The invention also discloses a kind of application process of cyanide ion probe.The probe good water solubility, cyanide ion can be detected in full aqueous medium, the response time is shorter than 20s, and Monitoring lower-cut reaches 55nM.In addition to carbonate and phosphate radical can produce weak interference, detection of other Common Anions to cyanide ion has no effect.Therefore, quick detection and monitoring of the probe available for cyanide ion content in food, medicine, agricultural product, dyestuff and drinking-water.
Description
Technical field
The invention belongs to the quick detection of cyanide ion content and monitoring technology field, is specifically related to a kind of based on aggregation
Cyanide ion probe, preparation and the application of state Fluorescence effects.
Background technology
Cyanide is a kind of highly important industrial chemicals, is widely used in plating, metallurgy, synthetic dyestuffs, synthetic fibers, conjunction
The fields such as resin, substantial amounts of cyanide is especially needed to use to carry out the dump leaching of mineral in exploitation of gold deposit.It is estimated that the whole world
About 1,500,000 tons of the cyanide consumed every year.However, the toxicity of cyanide is also very high, mammal can pass through lung, digestion
Road, skin etc. are absorbed, and it is vomitted by suppressing the normal work of cytochrome oxidase on mitochondria produce poisoner
Tell, faint from fear, the loss of consciousness, even death, minimum lethal dose is usually 0.5-3.5mg/kg body weight.Industry Waste containing cyanide
Pollution of the water to underground and earth surface water source causes our drinking water safety risk increase, and exploitation rapidly and efficiently detection is drunk with monitoring
The content of cyanide ion becomes very urgent in water.Further, since the necleophilic reaction performance that cyanide ion is good, it is also a large amount of
Applied to the synthesis of medicine intermediate, thus a kind of reagent of cyanide remnants in medicine that sensitive can detect is developed to ensureing the people
Masses' health is also particularly significant.
Fluorescence detection has the advantages that high sensitivity, Monitoring lower-cut are low, accuracy is good, response is fast, equipment requirement is simple,
Turn into a kind of very important analysis detection means.In recent years, state of aggregation Fluorescence effects (AIE) receive the height of people
Degree is paid attention to, and the report that fluoroscopic examination is carried out using AIE effects is emerged in an endless stream.Compound with such effect does not have in the solution
Fluorescence, and have strong fluorescent emission under the conditions of the state of aggregations such as milkiness, suspended, colloid and solid.
When in fluorescence molecule simultaneously containing reprimand electron group with electron withdraw group, intramolecular electricity can be produced in the case where light excites
Lotus transfer effect (ICT), so as to solvent discoloration phenomenon occur, i.e., as solvent polarity increases, the launch wavelength of fluorescence molecule by
Gradually red shift, while fluorescence quantum yield declines.When two kinds of group electronic effect difference are more notable, or electronics be excited it is front and rear in sky
Between on distributional difference it is bigger, then ICT effects are stronger.Indoline salt not only has good water solubility, it may have strong
Electron-withdrawing power.When by itself and strong reprimand electronics base, such as 4-N, N- dimethylamino phenyls, benzene being introduced simultaneously in a manner of ortho position
When on ring, then HOMO and LUMO tracks that spatially electronics is independently distributed are generated.Due to extremely strong ICT effects, have
Fluorescence of the molecule of such structure in the intensive polar solvents such as water is thoroughly quenched.When the water that cyanide is added to this molecule
After solution, cyanide ion with indoline salt partial reaction, makes the fragment lose water-soluble and electron-withdrawing power rapidly, thus instead
The ICT effects in product are answered to weaken significantly, while the water-soluble reduction of product, it is presented coherent condition and caused in aqueous medium
Strong fluorescent emission, that is, produce AIE effects.
The content of the invention
The invention provides a kind of fluorescence probe water-soluble good and using AIE effects as luminous mechanism, there is response speed
Degree is fast, interference less, the advantages that Monitoring lower-cut is low, determinand dosage is few.
A kind of cyanide ion probe, i.e. (E)-[2 ˊ-(4-N, N- dimethylamino phenyl) vinyl] -1,3,3- trimethyl Yin
Diindyl quinoline salt compounded of iodine, its structural formula are as follows：
Present invention also offers a kind of preparation method of above-mentioned cyanide ion probe, including：O-bromobenzaldehye first with 4-
Suzuki reactions occur for (N, N- dimethylamino) phenyl pinacol borate, and then gained intermediate is again with 1,2,3,3- tetramethyls
Witting reactions occur for indoline salt compounded of iodine；Its synthetic route is as follows：
Intermediate 1 in above formula is 2- (4-N, N- dimethylamino phenyl) benzaldehyde, by o-bromobenzaldehye and 4-N, N- bis-
Which alcohol ester of methylamino phenyl boric acid piece is in Isosorbide-5-Nitrae-dioxane/water (4:1, volume ratio) close palladium in mixed liquor, with four (triphenyl phosphorus)
(5%mol) be catalyst, using cesium carbonate as acid binding agent, 80 DEG C~100 DEG C at obtain after heating response 10h~20h；Among this
Body then with obtained after 1,2,3,3- tetramethyl indolines salt compounded of iodine in methyl alcohol 18~24h of back flow reaction cyanide ion probe (E)-
[2 '-(4-N, N- dimethylamino phenyl) vinyl] -1,3,3- tri-methyl indole quinoline salt compounded of iodine, i.e. probe in above formula.
The probe of gained of the invention is peony flat crystal, stable in the air, can be preserved for a long time in dry conditions
And never degenerate.The compound has good water solubility, and with the increase of its content in the aqueous solution, solution colour is gradually by pale yellow
It is rufous that color, which is deepened,.
Present invention also offers the application side that a kind of above-mentioned probe is detected under the conditions of full aqueous medium to cyanide ion
Method.
Experiment shows that after adding cyanide ion in the probe aqueous solution, solution colour is taken off rapidly by original yellowish-brown
Become colorless, the change of color with the naked eye can also understand in the sunlight differentiates.Under 365nm ultraviolet lights, add cyanogen root from
Bright blue-fluorescence is presented in solution after son, and does not add the probe solution before cyanide ion not have any fluorescence (see accompanying drawing
1).The probe solution added with the light beam irradiation of red laser pen after cyanide ion, can clearly seeing a branch of red light path, (fourth reaches
That effect), and original probe ion aqueous solution is irradiated then without this phenomenon (see accompanying drawing 2), illustrate that the former has formed state of aggregation.Cause
This, the probe is to detect cyanide ion based on AIE effects.
We carry out quantitative detection using fluorescent spectrometry to the performance of the cyanide ion probe, before and after acquisition probe adds
Fluorescence intensity of the system at 435nm.Experiment shows, after the cyanide ion aqueous solution is added to 20s in the probe aqueous solution, body
The fluorescence intensity of system no longer extends with further change with the time, illustrates that the probe can be completed to cyanogen root within 20s
The response of ion (see accompanying drawing 3)；Probe reaches 1 with cyanogen root dosage:During 3 equivalent proportion, the fluorescence intensity of system increases there is no obvious
Add, illustrate that the probe at most only needs 3 equivalent cyanide ions to produce stable fluorescence response (see accompanying drawing 4 and accompanying drawing 5).
In addition, in addition to carbanion and phosphate anion can produce faint fluorescence with probe effect, other
The no any interference of detection of more than the 20 kinds of common anion to probe illustrates the probe to cyanide ion (see accompanying drawing 6)
Detection has very excellent selectivity.We determine fluorescence intensity-concentration curve under relatively low cyanide ion concentration (see attached
Insertion portion in Fig. 5), obtain the slope of a curve.According to(wherein σ is plus before cyanide ion probe is not water-soluble to formula
Liquid carries out the standard deviation of the fluorescence intensity level of 20 measurements at 435nm,To measure obtained fluorescence intensity-concentration curve
Slope), it is 55nM to the Monitoring lower-cut value of cyanide ion concentration that the probe, which is calculated, is determined well below the World Health Organization
1.9 μM of safty of drinking water standard.Using when, preferably, cyanide ion concentration is at least 55nM in solution to be detected.
This item purpose is beneficial in that：
(1) the invention provides a kind of new cyanide ion probe based on AIE luminous mechanisms；
(2) probe of the invention can carry out the detection of cyanide ion in full aqueous medium, be expected to be applied to living biological cell
The fluorescent tracing and imaging of middle cyanide ion；
(3) probe of the invention has the response being exceedingly fast to cyanide ion, and detecting can complete in 20s, can be applied to
Field quick detection and monitoring to cyanide ion；
(4) probe of the invention reaches 55nM to the Monitoring lower-cut of cyanide ion concentration, more than many other types of cyanogen
Radical ion probe, also testing requirements considerably beyond World Health Organization to cyanide ion content in safty of drinking water；
(5) detection of probe of the invention to cyanide ion has excellent selectivity, and other common anion do not produce
Raw interference.
In summary, the probe good water solubility, cyanide ion can be detected in full aqueous medium, the response time is short,
Testing requirements of the Monitoring lower-cut well below World Health Organization to cyanide ion content in safty of drinking water.Can except carbonate and phosphate radical
Produce outside weak interference, detection of other Common Anions to cyanide ion has no effect.Therefore, the probe can be used for eating
The quick detection of cyanide ion content and monitoring in product, medicine, agricultural product, dyestuff and drinking-water.
Brief description of the drawings
Fig. 1 is the probe aqueous solution (B portions under daylight (part A) and 365nm ultraviolet lights before and after addition cyanide ion
Point) photo；
Fig. 2 is adds before cyanide ion (part A) with (part B) the probe aqueous solution afterwards under red laser beam irradiation
Photo；
Fig. 3 be add cyanide ion after reaction time-fluorescence intensity relation curve (during measurement concentration and probe concentration be 20 μM,
Cyanide ion concentration is 60 μM, sampling interval 0.06s)；
Fig. 4 is the ion concentration-fluorescence intensity spectrogram added after cyanide ion (concentration and probe concentration is 20 μM during measurement)；
Fig. 5 is the ion concentration-fluorescence intensity relation curve added after cyanide ion (concentration and probe concentration is 20 μM during measurement)；
Fig. 6 is that (concentration and probe concentration is 20 μM to fluorescence intensity of the different anions to probe response during measurement, and potassium cyanide concentration is
60 μM, other testing concentrations are 200 μM；Black post：Probe+anion；Gray columns：Probe+anion+cyanide ion；1-23:CN
-, CO3 2-, PO4 3-, SCN-, HS-, S2-, SO4 2-, HSO4 -, S2O3 2-, HPO4 2-, H2PO4-, F-, Cl-, Br-, I-, N3-, NO2-,
NO3-, HCO3-, OAc-, HSO3-, SO3 2-, ClO4ˉ)；
Fig. 7 is intermediate 11H-NMR spectrum；
Fig. 8 is intermediate 113C-NMR spectrograms；
Fig. 9 is the EI-MS spectrograms of intermediate 1；
Figure 10 is probe molecule1H-NMR spectrum；
Figure 11 is probe molecule13C-NMR spectrograms；
Figure 12 is the EI-MS spectrograms of probe molecule.
Embodiment
Embodiment 1：The synthesis of intermediate 2- (4-N, N- dimethylamino phenyl) benzaldehyde 1
Under room temperature and nitrogen stream atmosphere, by 4-N, two Evil of N- dimethylamino phenyl boric acids piece any alcohol ester (20mmol, 4.92g)
Alkane/water mixed solution (20mL, 4:1 volume ratio) with syringe injection fill o-bromobenzaldehye (18mmol, 3.31g), cesium carbonate
(20mmol, 3.88g) and four (triphenyl phosphorus) conjunction palladium (0.9mmol, 1.07g) dioxanes/water mixed solution (30mL, 4:1 body
Product ratio) in.Mixture is cooled to room temperature at 90 DEG C after heating response 16h, by reacting liquid filtering, gained filtrate water
(150mL) dilutes, and is extracted with ethyl acetate (3 × 20mL).The extract of merging filters after anhydrous sodium sulfate drying, filtrate
Concentrate on a rotary evaporator, the isolated light yellow powder solid 3.36g of residual solution silica gel column chromatography, yield 83%.
The fusing point of intermediate 1, nucleus magnetic hydrogen spectrum data, nuclear-magnetism carbon modal data, EI-MS mass spectrometric datas difference are as follows：
m.p.77.4-79.3℃；1H NMR(400MHz,CDCl3) δ 2.93 (s, 6H), 6.71 (d, J=7.6Hz, 2H),
7.17 (d, J=8.0Hz, 2H), 7.31-7.37 (m, 2H), 7.50 (t, J=7.6Hz, 1H), 7.79 (d, J=8.0Hz, 1H),
9.94(s,1H)；13C NMR(100MHz,CDCl3)δ40.58,112.05,126.63,127.54,130.63,131.10,
133.42,133.61,146.30,150.26,193.54；EI-MS (70eV) m/z (%) 225 (M+,100),196(45),182
(29),167(12),152(49),141(13),128(17),115(17),69(23),51(25),42(47).
Intermediate 11H-NMR spectrum such as Fig. 7,13C-NMR spectrograms such as Fig. 8, EI-MS spectrograms such as Fig. 9.
Embodiment 2：Probe (E)-[2 '-(4-N, N- dimethylamino phenyl) vinyl] -1,3,3- tri-methyl indole quinoline iodine
The synthesis of salt
At room temperature, the methanol solution (25mL) of 1,2,3,3- tetramethyl indoline salt compounded of iodine (20mmol, 6.02g) is added dropwise
Enter into the methanol solution (25mL) of above-mentioned intermediate 1 (18mmol, 4.05g).Reaction solution is cooled to room after being heated to reflux 24h
Temperature, the precipitation of generation is filtered, filter cake is recrystallized again with methanol, obtains peony flat crystal (E)-[2 '-(4-N, N- bis-
Methylaminophenyl) vinyl] -1,3,3- tri-methyl indole quinoline salt compounded of iodine 5.76g, yield 63%.
(E)-[2 '-(4-N, N- dimethylamino phenyl) vinyl] fusing point, the nuclear-magnetism of -1,3,3- tri-methyl indole quinoline salt compounded of iodine
Hydrogen modal data, nuclear-magnetism carbon modal data, EI-MS mass spectrometric datas difference are as follows：
m.p.234.2--235.9℃；1H NMR(400MHz,CDCl3)δ1.53(s,6H),3.00(s,6H),4.15(s,
3H), 6.87 (d, 2H, J=8.4Hz), 7.25 (d, 2H, J=8.8Hz), 7.52-7.69 (m, 5H), 7.73 (d, 1H, J=
16.4Hz), 7.81 (d, 1H, J=7.2Hz), 7.90 (d, 1H, J=7.2Hz), 8.14 (d, 1H, J=16.4Hz), 8.38 (d,
1H, J=7.6Hz)；13C NMR(100MHz,CDCl3)δ25.28,34.62,51.86,112.02,113.44,115.24,
122.82,125.88,127.21,128.25,129.01,129.42,130.46,130.77,131.64,132.81,141.75,
143.08,145.17,150.22,151.61,181.66；EI-MS (70eV) m/z (%) 382 (M++1-I-,46),366(100),
352(23),246(33),221(44),208(23),178(14),165(17),158(68),144(34),127(13),115
(11).
- [2 '-(4-N, N- dimethylamino phenyl) vinyl] (E) -1,3,3- tri-methyl indole quinoline salt compounded of iodine1H-NMR is composed
Figure such as Figure 10,13C-NMR spectrograms such as Figure 11, EI-MS spectrograms such as Figure 12.
Embodiment 3：Measure of the aqueous solution middle probe to the cyanide ion response time
At room temperature, the manufacturing probe aqueous solution (20 μM) and cyaniding aqueous solutions of potassium are matched somebody with somebody in volumetric flask with deionized water respectively
(10mM) each portion.Take the probe solution (3mL) to be placed in quartz colorimetric utensil, and cuvette be positioned in XRF,
The standing wave long scan program of spectrometer is opened, it is strong with the fluorescence of sample under the sample frequency record 435nm of interval 0.06s once
Degree.Above-mentioned potassium cyanide solution (18 μ L) is injected in cuvette rapidly with micro syringe, sample when then recording different time
Fluorescent emission intensity under 435nm, experimental result are shown in Fig. 3.Experiment shows, when the cyanide ion aqueous solution, to be added to probe water-soluble
In liquid after 20s, the fluorescence intensity of system no longer extends with further change with the time, illustrates the probe within 20s
The response to cyanide ion can be completed.
Embodiment 4：Measure of the aqueous solution middle probe to cyanide ion detectable concentration
At room temperature, the manufacturing probe aqueous solution (1mM) and cyaniding aqueous solutions of potassium are matched somebody with somebody in volumetric flask with deionized water respectively
(10mM) each portion.Take the probe solution (0.2mL) to be placed in several 10mL volumetric flasks respectively, be sequentially added into bottle
Above-mentioned cyaniding aqueous solutions of potassium 2,3,4,5,6,7,8,10,12,14,16,20,26,32,40,50,60,70,80,100,120,
140th, 160,180,200 μ L, 10mL is settled to deionized water.After the reaction solution in volumetric flask shakes up and places 1min, respectively
Contain in quartz colorimetric utensil, the fluorescent emission intensity at 435nm is measured on XRF, as a result as shown in Figure 4 and Figure 5
(to clearly show that, CN is only provided in Fig. 4—Concentration is 10,20,26,32,40,50,60,70 μM of ion concentration-fluorescence spectrum
Figure).From Fig. 4 and Fig. 5, probe reaches 1 with cyanogen root dosage:During 3 equivalent proportion, the fluorescence intensity of system increases there is no obvious
Add, illustrate that the probe at most only needs 3 equivalent cyanide ions to produce stable fluorescence response.
Embodiment 5：Measure of the aqueous solution middle probe to anion selectivity
At room temperature, the manufacturing probe aqueous solution (1mM) and cyaniding aqueous solutions of potassium are matched somebody with somebody in volumetric flask with deionized water respectively
(10mM) each portion.Take the probe solution (0.2mL) to be placed in several 10mL volumetric flasks respectively, be separately added into bottle
Na2CO3,K3PO4,KSCN,NaHS,Na2S,Na2SO4,NaHSO4,Na2S2O3,K2HPO4, KH2PO4,KF,NaCl,NaBr,KI,
NaN3,NaNO2,KNO3,NaHCO3,NaOAc,NaHSO3,Na2SO3,NaClO4After the μ L of the aqueous solution (10mM) 200, deionized water is used
It is settled to 10mL.After the reaction solution in volumetric flask shakes up and places 1min, contain respectively in quartz colorimetric utensil, in XRF
Fluorescent emission intensity at upper measurement 435nm.
Take the probe solution (0.2mL) to be placed in several 10mL volumetric flasks respectively, Na is separately added into bottle2CO3,
K3PO4,KSCN,NaHS,Na2S,Na2SO4,NaHSO4,Na2S2O3,K2HPO4, KH2PO4,KF,NaCl,NaBr,KI,NaN3,
NaNO2,KNO3,NaHCO3,NaOAc,NaHSO3,Na2SO3、NaClO4After the μ L of the aqueous solution (10mM) 200, then add one by one above-mentioned
The μ L of cyaniding aqueous solutions of potassium 60,10mL is settled to deionized water.After the reaction solution in volumetric flask shakes up and places 1min, contain respectively
Enter in quartz colorimetric utensil, the fluorescent emission intensity at 435nm is measured on XRF.
Testing result is shown in Fig. 6.It will be appreciated from fig. 6 that except carbanion and phosphate anion can produce with probe effect
Outside faint fluorescence, detection no any interference of other more than 20 kinds of common anion to probe.
Claims (9)
- A kind of 1. cyanide ion probe, it is characterised in that it is (E)-[2 ˊ-(4-N, N- dimethylamino phenyl) vinyl] -1,3, 3- tri-methyl indole quinoline salt compounded of iodine, its structural formula are as follows：
- A kind of 2. preparation method of the cyanide ion probe described in claim 1, it is characterised in that including：O-bromobenzaldehye is first Suzuki reactions first occur with 4- (N, N- dimethylamino) phenyl pinacols borate, then gained intermediate is again with 1,2,3,3- Witting reactions occur for tetramethyl indoline salt compounded of iodine；Finally give (E)-[2 ˊ-(4-N, N- dimethylamino phenyl) vinyl]- 1,3,3- tri-methyl indole quinoline salt compounded of iodine.
- 3. a kind of cyanide ion probe according to claim 1 is in the mechanism realization pair by state of aggregation Fluorescence effects Application in the detection of cyanide ion.
- 4. cyanide ion probe according to claim 3 is realized to cyanogen root by the mechanism of state of aggregation Fluorescence effects Application in the detection of ion, it is characterised in that detection of the probe to cyanide ion carries out colorimetric under the conditions of daylight bore hole and sentenced It is disconnected.
- 5. cyanide ion probe according to claim 3 is realized to cyanogen root by the mechanism of state of aggregation Fluorescence effects Application in the detection of ion, it is characterised in that detection of the probe to cyanide ion carries out fluorescence judgement under ultraviolet light.
- 6. cyanide ion probe according to claim 3 is realized to cyanogen root by the mechanism of state of aggregation Fluorescence effects Application in the detection of ion, it is characterised in that when probe produces stable fluorescence response to cyanide ion, in solution to be detected Cyanogen root and the mol ratio of probe are 3:1.
- 7. cyanide ion probe according to claim 3 is realized to cyanogen root by the mechanism of state of aggregation Fluorescence effects Application in the detection of ion, it is characterised in that the time that probe produces stable fluorescence response to cyanide ion is no more than 20s.
- 8. cyanide ion probe according to claim 3 is realized to cyanogen root by the mechanism of state of aggregation Fluorescence effects Application in the detection of ion, it is characterised in that probe is 55nM to the Monitoring lower-cut of cyanide ion concentration.
- 9. cyanide ion probe according to claim 3 is realized to cyanogen root by the mechanism of state of aggregation Fluorescence effects Application in the detection of ion, it is characterised in that probe detects in full aqueous medium to cyanide ion.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610186488.0A CN105837492B (en) | 2016-03-28 | 2016-03-28 | A kind of cyanide ion probe, preparation and application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610186488.0A CN105837492B (en) | 2016-03-28 | 2016-03-28 | A kind of cyanide ion probe, preparation and application |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105837492A CN105837492A (en) | 2016-08-10 |
| CN105837492B true CN105837492B (en) | 2018-04-10 |
Family
ID=56583963
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610186488.0A Expired - Fee Related CN105837492B (en) | 2016-03-28 | 2016-03-28 | A kind of cyanide ion probe, preparation and application |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105837492B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106338513A (en) * | 2016-11-10 | 2017-01-18 | 广西大学 | Preparation method for chemosensing ensemble capable of measuring hydrogen ion colorimetric and application the same |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104357044A (en) * | 2014-10-14 | 2015-02-18 | 上海电力学院 | Fluorescent probe as well as preparation method and application thereof |
| CN104478855A (en) * | 2014-12-09 | 2015-04-01 | 上海应用技术学院 | 3-amino-4-((E)-pyridine-2(1-hydro)-alkenyl acetonitrile)-1,8-naphthalimide derivative |
| CN105038765A (en) * | 2015-06-16 | 2015-11-11 | 渤海大学 | Preparation method and application of high-selectivity cyanide ion fluorescent probe with AIEE property |
| CN105198910A (en) * | 2014-05-29 | 2015-12-30 | 安徽师范大学 | Turn-on-type BODIPY fluorescent sensor and its preparation method and use |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101298553B1 (en) * | 2011-08-12 | 2013-08-22 | 연세대학교 산학협력단 | Fluorescence probe for selective cyanide detection, method for preparing the same and method for selective cyanide detection |
-
2016
- 2016-03-28 CN CN201610186488.0A patent/CN105837492B/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105198910A (en) * | 2014-05-29 | 2015-12-30 | 安徽师范大学 | Turn-on-type BODIPY fluorescent sensor and its preparation method and use |
| CN104357044A (en) * | 2014-10-14 | 2015-02-18 | 上海电力学院 | Fluorescent probe as well as preparation method and application thereof |
| CN104478855A (en) * | 2014-12-09 | 2015-04-01 | 上海应用技术学院 | 3-amino-4-((E)-pyridine-2(1-hydro)-alkenyl acetonitrile)-1,8-naphthalimide derivative |
| CN105038765A (en) * | 2015-06-16 | 2015-11-11 | 渤海大学 | Preparation method and application of high-selectivity cyanide ion fluorescent probe with AIEE property |
Non-Patent Citations (1)
| Title |
|---|
| 蛋清生物模拟矿化合成荧光银纳簇和氰化物荧光探针;夏晓东，等;《无机化学学报》;20111230;第27卷(第12期);第2367-2371页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN105837492A (en) | 2016-08-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Ma et al. | Recent development of synthetic probes for detection of hypochlorous acid/hypochlorite | |
| Goswami et al. | A chemodosimeter for the ratiometric detection of hydrazine based on return of ESIPT and its application in live-cell imaging | |
| Wu et al. | Excited state intramolecular proton transfer plus aggregation-induced emission-based diketopyrrolopyrrole luminogen: photophysical properties and simultaneously discriminative detection of trace water in three organic solvents | |
| Chen et al. | Determination of ammonia in water based on chemiluminescence resonance energy transfer between peroxymonocarbonate and branched NaYF4: Yb3+/Er3+ nanoparticles | |
| Ranyuk et al. | Diaminoanthraquinone-linked polyazamacrocycles: efficient and simple colorimetric sensor for lead ion in aqueous solution | |
| Ghorai et al. | A reversible fluorescent-colorimetric imino-pyridyl bis-Schiff base sensor for expeditious detection of Al 3+ and HSO 3− in aqueous media | |
| CN107345910B (en) | Fluorescent wide-chromaticity test paper for visually detecting copper ions and preparation method and application thereof | |
| Qi et al. | A highly sensitive and selective turn-off fluorescence sensor for Fe3+ detection based on a terbium metal-organic framework | |
| Xu et al. | A novel ratiometric colorimetric and NIR fluorescent probe for detecting Cu2+ with high selectivity and sensitivity based on rhodamine-appended cyanine | |
| Pan et al. | AIE fluorescent probe based on tetraphenylethylene and morpholine-thiourea structures for detection of HClO | |
| Shiraishi et al. | Selective colorimetric sensing of Co (II) in aqueous media with a spiropyran–amide–dipicolylamine linkage under UV irradiation | |
| CN105647512B (en) | A kind of Cu2+Fluorescence probe, preparation method and applications | |
| Dong et al. | A new colorimetric and fluorescent chemosensor based on Schiff base-phenyl-crown ether for selective detection of Al3+ and Fe3+ | |
| Tavallali et al. | A new application of bromopyrogallol red as a selective and sensitive competition assay for recognition and determination of acetate anion in DMSO/water media | |
| Tang et al. | Attractive benzothiazole-based fluorescence probe for the highly efficient detection of hydrogen peroxide | |
| Wu et al. | A novel “on-off-on” acylhydrazone-based fluorescent chemosensor for ultrasensitive detection of Pd2+ | |
| CN103387830B (en) | Chromium-ion ratio type fluorescence probe as well as preparation method and application thereof | |
| Slassi et al. | A novel imidazole‐derived Schiff base as selective and sensitive colorimetric chemosensor for fluorescent detection of Cu2+ in methanol with mixed aqueous medium | |
| Murugan et al. | Fluorescent sensor for in-vivo bio-imaging, precise tracking of Fe3+ ions in Zebrafish embryos and visual measuring of Cu2+ ions in pico-molar level | |
| He et al. | A naphthalimide functionalized fluoran with AIE effect for ratiometric sensing Hg2+ and cell imaging application | |
| Ren et al. | An OFF–ON–OFF type fluorescent probe based on a naphthalene derivative for Al3+ and F− ions and its biological application | |
| Feng et al. | Real-time detection and imaging of exogenous and endogenous Zn 2+ in the PC12 cell model of depression with a NIR fluorescent probe | |
| Yu et al. | Enhancing probe’s sensitivity for peroxynitrite through alkoxy modification of dicyanovinylchromene | |
| CN105319194B (en) | A kind of method that I and Hg2+ are continuously detected using aggregation-induced emission type fluorescence sense molecule | |
| CN105837492B (en) | A kind of cyanide ion probe, preparation and application |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20180410 Termination date: 20190328 |
|
| CF01 | Termination of patent right due to non-payment of annual fee |