CN116751210A - Water-soluble probe for detecting mercury ions and preparation method and application thereof - Google Patents
Water-soluble probe for detecting mercury ions and preparation method and application thereof Download PDFInfo
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- CN116751210A CN116751210A CN202310683781.8A CN202310683781A CN116751210A CN 116751210 A CN116751210 A CN 116751210A CN 202310683781 A CN202310683781 A CN 202310683781A CN 116751210 A CN116751210 A CN 116751210A
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- probe
- mercury ions
- compound
- mercury
- ions
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- 239000000523 sample Substances 0.000 title claims abstract description 103
- -1 mercury ions Chemical class 0.000 title claims abstract description 91
- 229910052753 mercury Inorganic materials 0.000 title claims abstract description 90
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 33
- 238000001514 detection method Methods 0.000 claims abstract description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000000243 solution Substances 0.000 claims description 59
- 238000012360 testing method Methods 0.000 claims description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical compound [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 claims description 10
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 claims description 10
- 229940126214 compound 3 Drugs 0.000 claims description 8
- 229940125782 compound 2 Drugs 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- 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 5
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 5
- NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 claims description 5
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 5
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 5
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 claims description 5
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 5
- 229940117953 phenylisothiocyanate Drugs 0.000 claims description 5
- UGOMMVLRQDMAQQ-UHFFFAOYSA-N xphos Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 UGOMMVLRQDMAQQ-UHFFFAOYSA-N 0.000 claims description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 239000002537 cosmetic Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 239000008213 purified water Substances 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 abstract description 27
- 230000035484 reaction time Effects 0.000 abstract description 8
- 150000003457 sulfones Chemical class 0.000 abstract description 4
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 15
- 238000002835 absorbance Methods 0.000 description 14
- 230000008859 change Effects 0.000 description 14
- 150000002500 ions Chemical class 0.000 description 14
- 239000007864 aqueous solution Substances 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000011550 stock solution Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000000862 absorption spectrum Methods 0.000 description 8
- 230000002452 interceptive effect Effects 0.000 description 7
- 239000008363 phosphate buffer Substances 0.000 description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
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- 208000003351 Melanosis Diseases 0.000 description 4
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
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- 239000012044 organic layer Substances 0.000 description 3
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- 238000001228 spectrum Methods 0.000 description 3
- 125000000542 sulfonic acid group Chemical group 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- ICNFHJVPAJKPHW-UHFFFAOYSA-N 4,4'-Thiodianiline Chemical compound C1=CC(N)=CC=C1SC1=CC=C(N)C=C1 ICNFHJVPAJKPHW-UHFFFAOYSA-N 0.000 description 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 239000003068 molecular probe Substances 0.000 description 2
- PSBAIJVSCTZDDB-UHFFFAOYSA-N phenyl acetylsalicylate Chemical compound CC(=O)OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 PSBAIJVSCTZDDB-UHFFFAOYSA-N 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000989913 Gunnera petaloidea Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 1
- WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical compound [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 description 1
- 238000003723 Smelting Methods 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000003968 anodic stripping voltammetry Methods 0.000 description 1
- 238000001479 atomic absorption spectroscopy Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- WLZRMCYVCSSEQC-UHFFFAOYSA-N cadmium(2+) Chemical compound [Cd+2] WLZRMCYVCSSEQC-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003915 cell function Effects 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910001430 chromium ion Inorganic materials 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000011033 desalting Methods 0.000 description 1
- LISMWBDWCFWBMB-UHFFFAOYSA-N dicyclohexylphosphane 2-phenyl-1,3,5-tri(propan-2-yl)benzene Chemical group C1(CCCCC1)PC1CCCCC1.C(C)(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)C1=CC=CC=C1 LISMWBDWCFWBMB-UHFFFAOYSA-N 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical group C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000001095 inductively coupled plasma mass spectrometry Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- RVPVRDXYQKGNMQ-UHFFFAOYSA-N lead(2+) Chemical compound [Pb+2] RVPVRDXYQKGNMQ-UHFFFAOYSA-N 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 229910001437 manganese ion Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229960003966 nicotinamide Drugs 0.000 description 1
- 235000005152 nicotinamide Nutrition 0.000 description 1
- 239000011570 nicotinamide Substances 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000004537 pulping Methods 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
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- 239000008434 yi-zhi Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
- C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
-
- 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"
-
- 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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- 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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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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
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
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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
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Optics & Photonics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
The invention discloses a water-soluble probe for detecting mercury ions, a preparation method and application thereof, wherein the molecular formula of the probe is C 35 H 33 N 5 O 6 S 3 The structural formula isThe probe prepared by the invention introduces sulfone into the spiro rhodamine derivative, so that the spiro rhodamine derivative has good water solubility; in addition, the probe has excellent selectivity on mercury ions, can specifically identify the mercury ions, is used for detecting the mercury ions, and can accelerate the reaction rate of the probe and the mercury ions after Sodium Dodecyl Sulfate (SDS) is added into a detection system, so that the reaction time reaches equilibrium from about 15 minutes to 90 percent of the original reaction time, and the reaction time is shortened to 1 minute.
Description
Technical Field
The invention relates to the technical field of small organic molecule probes, in particular to a water-soluble probe for detecting mercury ions, and a preparation method and application thereof.
Technical Field
With activities such as metal smelting, cement industry, household garbage incineration, landfill, petroleum burning, volcanic eruption, etc., mercury ions are increasingly released into our living environment, wherein artificially discharged mercury accounts for seventy-five percent of the total discharge. Because mercury ions have a high affinity for thiol groups in proteins and enzymes, even low concentrations of mercury ions can disrupt cellular functions, leading to the development of brain, kidney and nervous system related diseases. Various methods of mercury ion detection exist, such as anodic stripping voltammetry, inductively coupled plasma-mass spectrometry, atomic absorption spectroscopy, and high performance liquid chromatography, but these methods are limited by expensive equipment and complex sample pretreatment. Compared with the currently reported instrument technology for detecting mercury ions, the small molecular probe has the advantages of low cost, high selectivity, good anti-interference performance and the like.
In the small molecular probe, rhodamine and the derivative thereof are widely applied due to the long absorption and emission wavelength, high molar extinction coefficient, good light stability and high fluorescence quantum yield. Rhodamine and its derivatives are colorless in the spiro form, and the corresponding spirolactams turn pink after ring opening. When a proper ligand is introduced on the spirolactam ring, metal ions are added to induce the spirolactam ring to open so as to change the color, so that rhodamine and the derivative thereof can be used as an ideal skeleton for detecting mercury ions. Commercial rhodamine has good water solubility due to containing hydrophilic groups, but most of the rhodamine derivatives in the spiro form reported at present have poor water solubility, and at least 15% of organic solvent (such as ethanol, tetrahydrofuran, dimethyl sulfoxide, dimethylformamide and the like) needs to be added for dissolution in the detection process. Many organic solvents are toxic, their addition can be hazardous to the human body and the environment, and may require more complex operations. The method of improving the water solubility of the compound is usually to introduce a sulfonic acid group, but this results in that the probe introduced with the sulfonic acid group cannot penetrate the cell membrane due to the negative charge of the sulfonic acid group, and synthesis and separation are difficult and expensive due to the large polarity of the molecule. Therefore, development of rhodamine derivatives with neutral molecules and good water solubility is of great importance.
Common reactions for detecting mercury ions are mainly desalting, hydrolysis, mercurification and interaction with sulfur. Because mercury ions have a strong affinity for sulfur, probes that interact with sulfur have good selectivity and high sensitivity, but require a longer reaction time or an excess of mercury ions. Therefore, how to increase the reaction rate with mercury ions while achieving better selectivity of the probe is a problem to be solved.
Disclosure of Invention
The invention provides a sulfobenzide substituted rhodamine thioaniline probe and a preparation method and application thereof, which take the good biocompatibility of dimethyl sulfoxide (DMSO) into consideration, and after introducing sulfone on rhodamine derivatives, the water solubility of the probe is improved, the problem of poor water solubility of a spiro-type rhodamine probe is solved, and the purpose of reducing environmental pollution is achieved; meanwhile, the reaction rate is improved by adding Sodium Dodecyl Sulfate (SDS), the problem that the time for detecting mercury ions by a probe reacting with sulfur is long is solved, and the rhodamine derivative with a colorless spiro structure turns pink after being combined with the mercury ions, so that the aim of detecting the mercury ions by naked eyes is fulfilled.
The technical scheme for realizing the invention is as follows:
a water-soluble probe for detecting mercury ions is a thioaniline probe of sulfone substituted rhodamine, and the molecular formula of the probe is C 35 H 33 N 5 O 6 S 3 The structural formula is
The preparation method of the water-soluble probe for detecting mercury ions comprises the following steps:
(1) Placing fluorescein in a round bottom flask, adding anhydrous dichloromethane, cooling to 0 ℃ in an ice bath, adding anhydrous pyridine and trifluoromethanesulfonic anhydride in sequence, and stirring for 4 hours at room temperature to obtain a compound 2;
(2) Placing a compound 2, tris (dibenzylideneacetone) dipalladium, X-Phos (dicyclohexylphosphine-2 ',4',6' -triisopropylbiphenyl), cesium carbonate and thiomorpholine-1, 1-dioxide in a round-bottom flask, adding 1, 4-dioxane, and carrying out reflux reaction at 101 ℃ under the protection of nitrogen for overnight to obtain a compound 3;
(3) Adding the compound 3 into a round-bottom flask, dissolving with methanol, slowly adding hydrazine hydrate, and then heating to 65 ℃ for reflux reaction for 6-8h to obtain a compound 4;
(4) Compound 4 was added to a round-bottomed flask, dissolved in anhydrous dimethylformamide, and then a dimethylformamide solution containing phenyl isothiocyanate was slowly added thereto, and the reaction was stirred at room temperature overnight to give the probe.
The mass ratio of the fluorescein to the trifluoromethanesulfonic anhydride in the step (1) is 1:4.
The mass ratio of the substances of the compound 2, the tris (dibenzylideneacetone) dipalladium, the X-Phos, the cesium carbonate and the thiomorpholine-1, 1-dioxide in the step (2) is 10:1:3:27.7:23.6.
The mass ratio of the compound 3 and the hydrazine hydrate in the step (3) is 1:3.3.
The mass ratio of the compound 4 to the phenylisothiocyanate in the step (4) is 1:0.015.
The probe is applied to mercury ion detection.
The detection method for the application comprises the following steps:
s1: dissolving the probe in DMSO to prepare a 2mM stock solution of the probe, and adding the stock solution of the probe to 10mM phosphate buffer PB at ph=7.4;
s2: adding aqueous solutions of mercury ions with different equivalent weights into the mixed solution obtained in the step (1) to enable the final concentration of the probe to be 6 mu M, measuring the ultraviolet absorption spectrum change of each solution before and after the reaction, observing the color change of each solution before and after the reaction under a fluorescent lamp, and establishing a standard working curve or a judgment standard according to a test result;
s3: and (3) adding the aqueous solution of the sample to be detected into the mixed solution obtained in the step (1) to enable the final concentration of the probe to be 6 mu M, detecting on an ultraviolet spectrophotometer, and judging the mercury ion content in the aqueous solution of the sample to be detected according to the detection result.
The step S1 also comprises a step of adding SDS, wherein the SDS can accelerate the reaction rate of the probe and mercury ions, and does not influence the detection of the mercury ions.
Changes in reaction time before and after SDS addition: under the condition of no SDS, the reaction rate of the probe and mercury ions is gradually accelerated along with the increase of the concentration of mercury ions in the solution, and the probe and mercury ions reach equilibrium in about 15 minutes; when 2mM SDS was added, the reaction rate of the probe with mercury ions was significantly increased, and 90% of the reaction could be achieved in 1 minute.
Changes in ultraviolet absorbance spectra before and after addition of mercury ions: along with the increase of the concentration of mercury ions, the absorption peak of the solution at 543nm is gradually increased, the absorbance of the solution at 543nm and the concentration of mercury ions show a good linear relationship, and the quantitative detection of mercury ions can be realized according to the change of the ultraviolet absorption spectrum.
The probe is used for detecting mercury ions in purified water and cosmetics.
The application of the probe in the mercury ion detection test strip takes the test strip as a carrier, and the probe is loaded on the test strip to realize the detection of mercury ions.
The beneficial effects of the invention are as follows:
(1) Compared with other probes for detecting mercury ions through rhodamine derivatives in the prior art, the method has the advantages that the methylamino of the spirocyclic rhodamine is replaced by sulfone, so that the water solubility of the spirocyclic rhodamine is improved, and the technical problem that organic solvents are needed for detecting mercury ions by the spirocyclic rhodamine probes in the prior art is solved;
(2) When the method is used for detecting the mercury ions, the reaction time reaches equilibrium from about 15 minutes after 2mM SDS is added, the reaction time is shortened to 90% after 1 minute, and the problem of long reaction time with a probe for detecting the mercury ions due to the action of sulfur is solved, so that the rapid detection of the mercury ions is realized.
Drawings
In order to more clearly illustrate the embodiments of the invention or the technical solutions in the prior art, the drawings that are required in the embodiments or the description of the prior art will be briefly described, it being obvious that the drawings in the following description are only some embodiments of the invention, and that other drawings may be obtained according to these drawings without inventive effort for a person skilled in the art.
FIG. 1 is a synthetic route diagram of a probe;
FIG. 2 shows the probe prepared in example 1 1 H NMR spectrum;
FIG. 3 shows the probe prepared in example 1 13 C NMR spectrum;
FIG. 4 is a graph (A) showing the absorbance at 543nm of a solution when the probe prepared in example 1 was reacted with mercury ions at different concentrations in a PB (10 mM, pH=7.4) system, and a graph (B) showing the absorbance at 543nm of a solution when 6. Mu.M probe was reacted with 6. Mu.M mercury ions in the presence of SDS at different concentrations.
FIG. 5 is a graph (A) showing ultraviolet absorption spectra of a solution after the probe prepared in example 1 reacts with mercury ions of different concentrations in the presence of 2mM SDS, a graph (B) showing a linear fit of absorbance at 543nm of the solution to the concentration of mercury ions, and a graph (C) showing a change in color of the solution under a fluorescent lamp;
FIG. 6 is a graph showing the absorbance histogram (A) at 543nm and the color change chart (C) of a solution under a fluorescent lamp after the probe prepared in example 1 reacts with mercury ions and different interfering ions, respectively, in the presence of 2mM SDS, and a graph showing the absorbance histogram (B) at 543nm and the color change chart of a solution under a fluorescent lamp in the presence of the probe, mercury ions and different interfering ions;
fig. 7 is a color change chart (a) of the probe load test strip under a fluorescent lamp before and after the probe load test strip reacts with mercury ions with different concentrations, a change relation chart (B) of "(g+b)/2R" values along with the concentration of the mercury ions, and a schematic diagram (C) of a process of the test strip for detecting the mercury ions.
Detailed Description
The technical solutions of the present invention will be clearly and completely described in conjunction with the preferred embodiments of the present invention, and it is apparent that the described embodiments are only some embodiments of the present invention, not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without any inventive effort, are intended to be within the scope of the invention.
Example 1 Synthesis of probes
The preparation method of the probe has the technical route shown in figure 1, and comprises the following specific steps:
synthesis of Compound 2: in a 500mL round bottom flask, fluorescein (10.0 g) was added, and after anhydrous dichloromethane (200 mL) was added, the mixture was cooled to about 0deg.C in an ice bath, anhydrous pyridine (19.4 mL) and triflic anhydride (20.3 mL) were added successively, the reaction system was allowed to react at room temperature, the reaction progress was monitored by TLC, after 4h the reaction was completed, water was added to dilute and the aqueous phase was extracted 2-3 times with dichloromethane, and the organic layers were combined. After washing with water and saturated brine in this order, the solution was concentrated under reduced pressure to obtain a solution, and then the obtained compound 2 was purified by silica gel column chromatography using petroleum ether and ethyl acetate as eluent (petroleum ether: ethyl acetate=4:1). (15.6 g, 86.9%)
Synthesis of Compound 3: in a 500mL round-bottomed flask, compound 2 (5.0 g), tris (dibenzylideneacetone) dipalladium (0.77 g), X-Phos (1.2 g), cesium carbonate (7.6 g) and thiomorpholine-1, 1-dioxide (2.68 g) were added and dissolved with 1, 4-dioxane (100 mL). The reaction was left to react overnight under nitrogen at 101 ℃ under reflux, after completion of the reaction monitored by TLC, it was waited to cool to room temperature, diluted with water and the aqueous phase extracted 2-3 times with dichloromethane and the organic layers combined. Washing with water and saturated saline sequentially, drying, concentrating under reduced pressure to obtain a solution, pulping for 1-2h by adding methanol, and performing suction filtration through a glass sand core funnel to obtain a compound 3. (3.7 g, 77.9%)
Synthesis of Compound 4: in a 100mL round bottom flask, compound 3 (3.0 g) was added, dissolved in methanol (50 mL), and then hydrazine hydrate (0.84 mL) was slowly added. And heating the reaction system to 65 ℃ for reflux reaction, monitoring the reaction process by TLC, cooling to room temperature after the reaction is finished for 8 hours, and carrying out suction filtration through a glass sand core funnel to obtain the compound 4. (2.9 g, 94.3%)
Synthesis of probes: in a 100mL round bottom flask, compound 4 (1.0 g) was added, dissolved in anhydrous dimethylformamide (20 mL), and then dimethylformamide (10 mL dimethylformamide) containing phenyl isothiocyanate (2.6 mM) was slowly added. The reaction was stirred at room temperature, the reaction history was monitored by TLC, after the reaction was completed overnight, water was added to dilute and the aqueous layer was extracted 2-3 times with dichloromethane, and the organic layers were combined. After washing with water and saturated brine in this order, the solution was concentrated under reduced pressure, and the solution was purified by silica gel column chromatography using petroleum ether and ethyl acetate as eluents (petroleum ether: ethyl acetate=1:1) to obtain a probe. (0.5 g, 40.5%)
FIG. 2 is a nuclear magnetic resonance hydrogen spectrum of the probe prepared in example 1, showing the following data in the spectrum:
1 H NMR(400MHz,DMSO-d 6 )δ9.40(s,1H),9.01(s,1H),7.96–7.94(m,1H),7.68–7.64(m,2H),7.21–7.07(m,7H),6.76(d,J＝36Hz,4H),6.27(s,1H),3.81(s,8H),3.08(s,8H)。
FIG. 3 is a nuclear magnetic resonance carbon spectrum of the probe prepared in example 1, showing the following data:
13 C NMR(151MHz,DMSO)δ181.54,166.68,154.12,153.67,150.69,149.06,138.71,134.93,130.20,129.48,128.20,125.89,125.86,125.55,124.70,123.63,112.15,111.90,109.09,102.72,102.20,66.80,50.39,46.60。
from the above map data, the probe of the present invention was successfully synthesized.
Example 2 time response of probes to Mercury ions
The probe prepared in example 1 was dissolved in DMSO to prepare a 2mM probe stock solution;
the probe stock solution was added to 10mM phosphate buffer PB, pH=7.4, and various equivalents of aqueous solutions of mercury ions were added, respectively, so that the total volume of the solution was 2mL, the final concentration of the probe was 6. Mu.M, the final concentrations of mercury ions were 2. Mu.M, 4. Mu.M, 6. Mu.M, 8. Mu.M, 10. Mu.M, 12. Mu.M, and 14. Mu.M, respectively, and the absorbance at 543nm was varied with time.
The probe stock solution and the aqueous solution of mercury ions were added to 10mM, pH=7.4 phosphate buffer PB, and then aqueous solutions of different equivalents of SDS were added, respectively, so that the total volume of the solution was 2mL, the final concentration of the probe was 6. Mu.M, the final concentration of mercury ions was 6. Mu.M, and the final concentrations of SDS were 0mM, 0.5mM, 1mM, 2mM, 4mM, 6mM, 8mM, 10mM, respectively, and the absorbance at 543nm was varied with time.
As a result, as shown in fig. 4, in the case where SDS was not added, the reaction rate of the probe with mercury ions was gradually increased with the increase of the concentration of mercury ions in the solution, and equilibrium was reached for about 15 minutes (fig. 4A); when SDS with different concentrations is added, the reaction speed of the probe and mercury ions is obviously accelerated, and when the concentration of SDS is 2mM, the reaction can reach 90% in 1 minute, which indicates that the response speed of the probe to mercury ions is higher when SDS exists, and the probe can be used for detecting mercury ions in real time.
Example 3 change in absorbance spectra of probes after reaction with different equivalents of mercury ions
2mM of probe stock solution and SDS were added to 10mM of phosphate buffer PB having pH=7.4, then aqueous solutions of different equivalents of mercury ions were added respectively to make the total volume of the solutions 2mL, the final concentration of the probe was 6. Mu.M, the final concentration of SDS was 2mM, and the final concentrations of mercury ions were 0. Mu.M, 1. Mu.M, 2. Mu.M, 3. Mu.M, 4. Mu.M, 5. Mu.M, 6. Mu.M, 7. Mu.M, 8. Mu.M, 9. Mu.M, 10. Mu.M, respectively, and the ultraviolet absorption spectra of the respective solutions were tested and the colors of the respective solutions were observed under a fluorescent lamp.
As shown in fig. 5 (a), as the concentration of mercury ions in the solution increases, the absorption peak of the solution at 543nm increases gradually; as shown in FIG. 5 (B), the concentration of mercury ions is in the range of 1. Mu.M-8. Mu.M, the absorbance of the solution at 543nm shows a good linear relationship with the concentration of mercury ions, y= -0.03245+0.05229x, where y represents absorbance, x represents mercury ion concentration, R 2 = 0.9920, lower limit of quantitation is 1 μΜ; as shown in fig. 5 (C), the color of the solution gradually changed from colorless to pink as the concentration of mercury ions in the solution increased.
Example 4 investigation of the Selectivity and anti-interference Properties of the probes for different interfering ions
Preparing mercury ionsAqueous solutions of ions and other interfering ions, the concentration of the interfering ion aqueous solution being 10mM, the interfering ions comprising: potassium ion solution (K) + ) Calcium ion solution (Ca) 2+ ) Solution of zinc ion (Zn) 2+ ) Divalent cadmium ion solution (Cd) 2+ ) Trivalent chromium ion solution (Cr) 3+ ) Magnesium ion solution (Mg) 2+ ) Cupric ion solution (Cu) 2+ ) Divalent lead ion solution (Pb) 2+ ) Divalent manganese ion solution (Mn) 2+ ) Aluminum ion solution (Al 3+ ) And silver ion solution (Ag) + )；
(1) Selectivity experiment: and (3) setting a plurality of groups of experiments, wherein each group is prepared by adding probe stock solution and SDS into 10mM phosphate buffer PB with pH=7.4, taking one group of aqueous solution added with mercury ions, and adding the other groups of aqueous solutions with different interference ions respectively, so that the total volume of each group of solutions is 2mL, the final concentration of the probe is 6 mu M, the final concentration of the SDS is 2mM, the final concentration of the mercury ions is 10 mu M, the final concentration of the interference ions is 100 mu M, respectively testing the ultraviolet absorption spectrum of each solution, and observing the color change of each solution under a fluorescent lamp.
(2) Anti-interference experiment: and (3) setting a plurality of groups of experiments, adding a probe stock solution, SDS and mercury ion aqueous solution into 10mM phosphate buffer PB with pH=7.4, then adding different interference ion aqueous solutions into each group of solutions respectively, enabling the total volume of each group of solutions to be 2mL, enabling the final concentration of the probe to be 6 mu M, enabling the final concentration of the SDS to be 2mM, enabling the final concentration of the mercury ion to be 10 mu M, enabling the final concentration of the interference ion to be 100 mu M, testing the ultraviolet absorption spectrum of each solution respectively, and observing the color change of each solution under a fluorescent lamp.
Selectivity results: in the presence of other interfering ions, the absorbance of the probe cannot be changed obviously, only the mercury ions exist, the absorbance of the probe is increased obviously (figure 6A), and only the mercury ions can change the color of the solution under a fluorescent lamp (figure 6C), so that the probe has good selectivity to the mercury ions.
Anti-interference results: under the condition that other interference ions and mercury ions coexist, the absorbance of the probe can be obviously increased (figure 6B), all the solutions become pink in the presence of the mercury ions, and after a large amount of interference ions are added, the color of the solutions is not changed, so that the probe is verified to be not interfered by other metal ions.
Example 5 use of probes for detection of Mercury ions in practical samples
2 different purified water are taken, samples 1-2 are Yibao and Wa haha respectively, 4 different cosmetics are taken, and samples 3-6 are Yizhi spring water ripple whitening and freckle removing essence, BIOAOUA whitening and freckle removing cream, QISKINBO nicotinamide whitening and freckle removing cream and BAURSDE whitening and freckle removing cream digestion liquid respectively. The probe was used for detection, the mercury ion content in the actual sample was calculated from the absorbance and the linear equation obtained in example 3, and the mercury ions with concentration increments of 2. Mu.M, 4. Mu.M and 6. Mu.M were added to each of the above solutions, respectively, for the labeled recovery experiments, and the results are shown in Table 1.
TABLE 1 detection results of Mercury ions in actual samples and labeled recovery test results
Example 6 detection of Mercury ions by Probe-Supported test strips
2mM probe stock solution was added to 10mM phosphate buffer PB at pH=7 to prepare a probe solution having a probe concentration of 15. Mu.M, 8 test strips cut with filter paper into 1.4X0.7 cm were immersed in the probe solution, immersed for 10 minutes, and dried at room temperature (25 ℃) to obtain a probe-loaded test strip.
SDS was added to aqueous solutions of mercury ions of different concentrations to give final concentrations of SDS of 2mM, and final concentrations of mercury ions of 0. Mu.M, 2. Mu.M, 5. Mu.M, 10. Mu.M, 15. Mu.M, 20. Mu.M, 25. Mu.M, and 30. Mu.M, respectively, and the treated mercury ion solutions of different concentrations were added dropwise to the probe-loaded test strips, and color changes before and after reaction of the test strips with mercury ions were observed under a fluorescent lamp.
As shown in fig. 7, after the test strip loaded with the probe reacts with mercury ions under the fluorescent lamp, the test strip loaded with the probe turns pink (fig. 7A), indicating that the probe reacts with mercury ions on the test strip; fitting the color change of the test strip of the load probe under the fluorescent lamp by using the RGB of the mobile phone, and finding that the "(G+B)/2R" value and the concentration of mercury ions of the test strip show a good linear relation (FIG. 7B); fig. 7 (C) is a schematic diagram of a process of a probe-loaded test strip for mercury ion detection.
The experimental result shows that the probe prepared by the invention can be loaded on the test strip to simply and rapidly realize the detection of mercury ions in the solution.
The foregoing description of the preferred embodiments of the invention is not intended to be limiting, but rather is intended to cover all modifications, equivalents, alternatives, and improvements that fall within the spirit and scope of the invention.
Claims (9)
1. A water-soluble probe for detecting mercury ions is characterized in that the molecular formula of the probe is C 35 H 33 N 5 O 6 S 3 The structural formula is
2. The method for preparing a water-soluble probe for detecting mercury ions according to claim 1, comprising the steps of:
(1) Adding fluorescein and anhydrous dichloromethane into a reaction vessel, cooling in an ice bath, adding anhydrous pyridine and trifluoromethanesulfonic anhydride, and stirring to obtain a compound 2;
(2) Placing the compound 2, tris (dibenzylideneacetone) dipalladium, X-Phos, cesium carbonate and thiomorpholine-1, 1-dioxide in a reaction vessel, adding 1, 4-dioxane, and carrying out reflux reaction under the protection of nitrogen to obtain a compound 3;
(3) Dissolving the compound 3 with methanol, slowly adding hydrazine hydrate, and carrying out reflux reaction to obtain a compound 4;
(4) After dissolving the compound 4 by anhydrous dimethylformamide, slowly adding a dimethylformamide solution containing phenyl isothiocyanate, and stirring to obtain the probe.
3. The method according to claim 2, wherein the ratio of the amounts of the fluorescein and triflic anhydride in step (1) is 1:4.
4. The preparation process according to claim 2, wherein the mass ratio of the compounds 2, tris (dibenzylideneacetone) dipalladium, X-Phos, cesium carbonate and thiomorpholine-1, 1-dioxide in step (2) is 10:1:3:27.7:23.6.
5. The method according to claim 2, wherein the mass ratio of the compound 3 to the hydrazine hydrate in the step (3) is 1:3.3.
6. The method according to claim 2, wherein the mass ratio of the compound 4 to the phenylisothiocyanate in the step (4) is 1:0.015.
7. Use of the probe of claim 1 for mercury ion detection.
8. The use according to claim 7, for the detection of mercury ions in purified water and cosmetics.
9. The application of the probe in the mercury ion detection test strip, which is characterized in that the test strip is taken as a carrier, and the probe is loaded on the test strip to realize the detection of mercury ions.
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