CN108164448B - A kind of anthraquinone derivative and synthetic method and application - Google Patents
A kind of anthraquinone derivative and synthetic method and application Download PDFInfo
- Publication number
- CN108164448B CN108164448B CN201711439207.9A CN201711439207A CN108164448B CN 108164448 B CN108164448 B CN 108164448B CN 201711439207 A CN201711439207 A CN 201711439207A CN 108164448 B CN108164448 B CN 108164448B
- Authority
- CN
- China
- Prior art keywords
- compound
- preparation
- anthraquinone derivative
- ethyl alcohol
- compounds
- 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
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 150000004056 anthraquinones Chemical class 0.000 title claims abstract description 14
- 238000010189 synthetic method Methods 0.000 title abstract description 4
- BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical compound [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 claims abstract description 37
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 28
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- 235000019441 ethanol Nutrition 0.000 claims abstract description 19
- 238000010992 reflux Methods 0.000 claims abstract description 15
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims abstract description 6
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 claims abstract description 6
- 230000002378 acidificating effect Effects 0.000 claims abstract description 5
- 230000032050 esterification Effects 0.000 claims abstract description 5
- 238000005886 esterification reaction Methods 0.000 claims abstract description 5
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 5
- 239000007800 oxidant agent Substances 0.000 claims abstract description 4
- 230000001590 oxidative effect Effects 0.000 claims abstract description 4
- 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 abstract description 3
- 239000011261 inert gas Substances 0.000 claims abstract description 3
- 229940117953 phenylisothiocyanate Drugs 0.000 claims abstract description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- 239000007810 chemical reaction solvent Substances 0.000 claims description 4
- 229960000583 acetic acid Drugs 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 3
- 239000004327 boric acid Substances 0.000 claims description 3
- 229940117975 chromium trioxide Drugs 0.000 claims description 3
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 3
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 claims description 3
- 239000012362 glacial acetic acid Substances 0.000 claims description 3
- 239000012286 potassium permanganate Substances 0.000 claims description 3
- 239000005708 Sodium hypochlorite Substances 0.000 claims description 2
- 239000012445 acidic reagent Substances 0.000 claims description 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims description 2
- 239000000523 sample Substances 0.000 abstract description 31
- 238000001514 detection method Methods 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 238000000034 method Methods 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 43
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- LBJNMUFDOHXDFG-UHFFFAOYSA-N copper;hydrate Chemical compound O.[Cu].[Cu] LBJNMUFDOHXDFG-UHFFFAOYSA-N 0.000 description 9
- 239000011259 mixed solution Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 238000000862 absorption spectrum Methods 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000005909 ethyl alcohol group Chemical group 0.000 description 6
- 229910021645 metal ion Inorganic materials 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000002189 fluorescence spectrum Methods 0.000 description 5
- 239000012265 solid product Substances 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 230000005284 excitation Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 235000004237 Crocus Nutrition 0.000 description 3
- 241000596148 Crocus Species 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000012295 chemical reaction liquid Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229960001866 silicon dioxide Drugs 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- JJWSNOOGIUMOEE-UHFFFAOYSA-N Monomethylmercury Chemical compound [Hg]C JJWSNOOGIUMOEE-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- -1 filters while hot Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 150000001455 metallic ions Chemical class 0.000 description 2
- YXCDJKQYFBEAOU-UHFFFAOYSA-N phenyl thiocyanate Chemical compound N#CSC1=CC=CC=C1 YXCDJKQYFBEAOU-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008499 blood brain barrier function Effects 0.000 description 1
- 210000001218 blood-brain barrier Anatomy 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 238000005516 engineering process Methods 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
- 239000007788 liquid Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229940100892 mercury compound Drugs 0.000 description 1
- 150000002731 mercury compounds Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910001428 transition metal ion Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/285—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with peroxy-compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C241/00—Preparation of compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C241/04—Preparation of hydrazides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C337/00—Derivatives of thiocarbonic acids containing functional groups covered by groups C07C333/00 or C07C335/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C337/06—Compounds containing any of the groups, e.g. thiosemicarbazides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/255—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting
- C07C51/265—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting having alkyl side chains which are oxidised to carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- 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
- G01N21/17—Systems in which incident light is modified in accordance with the properties of the material investigated
- G01N21/25—Colour; Spectral properties, i.e. comparison of effect of material on the light at two or more different wavelengths or wavelength bands
- G01N21/31—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry
- G01N21/33—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry using ultraviolet light
-
- 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
-
- 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
- G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
- G01N21/77—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator
- G01N21/78—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator producing a change of colour
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
-
- 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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- 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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N2021/6443—Fluorimetric titration
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Immunology (AREA)
- General Health & Medical Sciences (AREA)
- Pathology (AREA)
- General Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Optics & Photonics (AREA)
- Molecular Biology (AREA)
- Plasma & Fusion (AREA)
- Materials Engineering (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of anthraquinone derivative and synthetic method and applications, belong to fluoroscopic examination field.This method is that oxidation reaction is carried out under the action of oxidant by chemical compounds I, and compound ii is prepared；Under acidic environment, compound ii carries out esterification with ethyl alcohol, obtains compound III；Under conditions of being heated to reflux, compound III is reacted with hydrazine hydrate, obtains compounds Ⅳ；In the environment of inert gas shielding, compounds Ⅳ is reacted with phenyl isothiocyanate, obtains compound V.Preparation method provided by the present invention is simple, is easy to industrialized production.And the multi signal probe that is prepared is low to the detection limit of mercury ion and high selectivity.
Description
Technical field
The present invention relates to fluoroscopic examination fields, and in particular to a kind of anthraquinone derivative and synthetic method and application.
Background technology
Industrial pollution leads to Hg2+Pollution in the environment has become very universal.Hg2+It is that there is serious physiological-toxicity
One of transition metal ions, once enter in ocean, inorganic Hg2+It can be changed under the action of bacterium and endanger bigger
Methyl mercury simultaneously enters in food chain, and methyl mercury is very notable to the harm of human body, it easily can be absorbed by the body and break through
Then the blood-brain barrier of human body directly acts on our central nervous system, is caused huge harm to human body.Therefore, it develops
It has great significance with the mercury ion and mercury compound detection method for studying novel.
Invention content
The purpose of the present invention can be achieved through the following technical solutions：
The structural formula of a kind of anthraquinone derivative, the derivative is as follows：
A kind of preparation method of above-mentioned anthraquinone derivative, this method reaction route are as follows：
Above-mentioned preparation method includes the following steps：
1) chemical compounds I carries out oxidation reaction under the action of oxidant, and compound ii is prepared；
2) under acidic environment, compound ii carries out esterification with ethyl alcohol, obtains compound III；
3) under conditions of being heated to reflux, compound III is reacted with hydrazine hydrate, obtains compounds Ⅳ；
4) in the environment of inert gas shielding, compounds Ⅳ is reacted with phenyl isothiocyanate, obtains compound V.
In technical solution of the present invention：Oxidation described in step 1) is chromium trioxide, potassium permanganate or sodium hypochlorite；Oxygen
It is ethyl alcohol or glacial acetic acid to change reaction solvent used.
In technical solution of the present invention：Acid reagent in step 2) used in acidic environment is sulfuric acid, phosphoric acid or boric acid,
The temperature of esterification is to be heated to reflux temperature.
In technical solution of the present invention：Step 3) reaction solvent used is methanol, ethyl alcohol or acetonitrile.
In technical solution of the present invention：The temperature of step 4) reaction is 0~100 DEG C, and the solvent for reacting used is methanol, second
Alcohol, acetonitrile or dichloromethane.
In technical solution of the present invention：Application of the anthraquinone derivative as detection mercury ion.
In technical solution of the present invention：The anthraquinone derivative application as detection mercury ion in the environment.
Beneficial effects of the present invention：
Preparation method provided by the present invention is simple, is easy to industrialized production.And the multi signal probe being prepared is to mercury
The detection limit of ion is low and high selectivity.
Description of the drawings
Fig. 1 is probe molecule ddpb to Hg2+Selective absorbing spectral matching factor.
Fig. 2 is Hg2+Figure is titrated to the absorption spectrum of probe molecule ddpb.
Fig. 3 is probe molecule ddpb to Hg2+Selective fluorescence spectrum identification.
Fig. 4 is Hg2+To the fluorescence spectroscopic titration figure of probe molecule ddpb.
Fig. 5 is Hg2+With the probe molecule ddpb reaction time to the influence diagram of solution fluorescence intensity.
Fig. 6 is when there is other coexistent metallic ions in solution to probe ddpb Selective recognitions Hg2+Influence diagram.
Fig. 7 is Hg2+The linear relationship chart of concentration and fluorescence intensity.
Specific implementation mode
With reference to embodiment, the present invention will be further described, and but the scope of the present invention is not limited thereto：
Embodiment 1
Be added in 100mL glacial acetic acid Isosorbide-5-Nitrae-dimethyl anthraquinone (10mmol, 2.36g) and chromium trioxide (100mmol,
10g), it is heated to reflux under stirring conditions 10 hours.It is cooled to room temperature, filters after reaction, obtained solid product is molten
It in 10% hot sodium hydroxide solution, filters while hot, solution ph is adjusted to 2 or so with concentrated hydrochloric acid after the cooling of gained filtrate,
It filters, obtained solid is washed with acetone, is dried in vacuo, is obtained faint yellow compound ii 2.77g, yield：93.6%, purity：
99.54%.
Elemental analysis：(%) for C16H8O6:Calculated value：C 64.87；H 2.72, measured value：C 65.18；H 2.85.
IR(KBr),ν,cm-1:3088,1780,1693,1674,1588,1373,1286,1257,1203,897,814,
747,683。
1H NMR(500MHz,CDCl3,TMS):δ=7.81 (d, J=6.8,2H), 8.34 (d, J=6.8,2H), 8.19
(s,2H),12.97(s,2H)ppm.
Compound ii (10mmol, 2.96g) and the 5mL concentrated sulfuric acids are added in 100mL absolute ethyl alcohols, is heated to reflux 6 hours.
After reaction, rotation is evaporated ethyl alcohol, obtained solid successively with 5% sodium carbonate liquor, be washed to neutrality, then washed with acetone,
Vacuum drying, obtains III 3.37g of yellow compound, yield：95.6%, purity：99.28%.
Elemental analysis：(%) for C20H16O6:Calculated value：C 68.18；H 4.58, measured value：C 68.73；H
4.37。
IR(KBr),ν,cm-1:3072,1732,1691,1578,1532,1497,1217,1138,961,819,767。
1H NMR(500MHz,CDCl3,TMS):δ=1.33 (t, J=7.0,6H), 4.36 (q, J=7.0,4H), 7.83
(d, J=6.8,2H), 8.32 (d, J=6.8,2H), 8.57 (s, 2H)
Compound III (10mmol, 3.52g), constant pressure under conditions of being heated to reflux are added in 100mL absolute ethyl alcohols
10mL hydrazine hydrates are slowly added dropwise in funnel, and the reaction was continued 6 hours after being added dropwise to complete.It is cooled to room temperature, will react after reaction
Liquid pours into the water of 100mL, is then extracted with ethyl acetate (50mL × 3), merges organic phase, and anhydrous magnesium sulfate is dried overnight,
Filtering obtains IV 3.07g of yellow compound, yield after rotating solvent evaporated：94.7%, purity：99.19%.Elemental analysis：(%)
for C16H12N4O4:Calculated value：C 59.26；H 3.73；N 17.28, measured value：C 59.17；H 3.41；N 17.46.
IR(KBr),ν,cm-1:3378,3284,3068,1697,1688,1642,1516,1482,1286,1329,1157,
932,827,715,674 1H NMR(500MHz,CDCl3,TMS):δ=3.87 (d, J=7.2,4H), 7.71 (d, J=7.0,
2H), 8.12 (d, J=6.8,2H), 8.38 (d, J=6.8,2H), 10.51 (br, 2H)
It is being passed through N2Under conditions of protection, compounds Ⅳ (10mmol, 3.24g) and different is added in 100mL anhydrous acetonitriles
Thiocyanic acid phenyl ester (22mmol, 2.97g) reacts 24 hours at room temperature.Solvent evaporated is rotated after reaction, by obtained solid
Product crosses silicagel column (ethyl acetate:Hexane=1:3), crocus compound V (ddpb) 5.53g of solvent, production is evaporated off in rotation
Rate：93.1%, purity：99.47%.
Elemental analysis：(%) for C30H22N6O4S2:Calculated value：C 60.59；H 3.73；N 14.13, measured value：C
61.13；H 3.84；N 13.91.
IR(KBr),ν,cm-1:3267,3216,3011,1721,1683,1632,1421,1207,1189,1157,878,
704,682。
1H NMR(500MHz,CDCl3,TMS):δ=3.67-3.71 (m, 4H), 4.38 (s, 2H), 6.95-7.03 (m,
6H), 7.16 (d, J=6.8,4H), 7.82 (d, J=6.8,2H), 8.03 (d, J=6.8,2H), 8.33 (d, J=6.8,2H)
Embodiment 2
Isosorbide-5-Nitrae-dimethyl anthraquinone (10mmol, 2.36g) and potassium permanganate are added in the ethanol solution of 100mL50%
(100mmol, 15.8g) is heated to reflux 12 hours under stirring conditions.It is cooled to room temperature, filters, by gained after reaction
Solid product is dissolved in 10% hot sodium hydroxide solution, is filtered while hot, and pH value of solution is adjusted with concentrated hydrochloric acid after the cooling of gained filtrate
It is worth 2 or so, filters, obtained solid is washed with acetone, is dried in vacuo, is obtained faint yellow compound ii 2.64g, yield：
89.1%, purity：99.17%.
Compound ii (10mmol, 2.96g) and 5mL phosphoric acid are added in 100mL absolute ethyl alcohols, is heated to reflux 8 hours.Instead
After answering, rotation is evaporated ethyl alcohol, obtained solid successively with 5% sodium carbonate liquor, be washed to neutrality, then washed with acetone, very
Sky is dry, obtains III 3.24g of yellow compound, yield：92.1%, purity：98.17%.
Compound III (10mmol, 3.52g), constant pressure under conditions of being heated to reflux are added in 100mL absolute methanols
15mL hydrazine hydrates are slowly added dropwise in funnel, and the reaction was continued 8 hours after being added dropwise to complete.It is cooled to room temperature, will react after reaction
Liquid pours into the water of 100mL, is then extracted with ethyl acetate (50mL × 3), merges organic phase, and anhydrous magnesium sulfate is dried overnight,
Filtering obtains IV 3.01g of yellow compound, yield after rotating solvent evaporated：92.8%, purity：99.17%.
It is being passed through N2Under conditions of protection, compounds Ⅳ (10mmol, 3.24g) and different is added in 100mL absolute ethyl alcohols
Thiocyanic acid phenyl ester (25mmol, 3.38g) reacts 30 hours at room temperature.Solvent evaporated is rotated after reaction, by obtained solid
Product crosses silicagel column (ethyl acetate:Hexane=1:3), crocus compound V (ddpb) 5.37g of solvent, production is evaporated off in rotation
Rate：90.3%, purity：98.16%.
Embodiment 3
Isosorbide-5-Nitrae-dimethyl anthraquinone (10mmol, 2.36g) is added in the ethanol solution of 100mL50%, is heated to reflux stirring.
Then the liquor natrii hypochloritis of 300mL 10% is slowly added dropwise with constant pressure funnel.Solution continues the condition in stirring after being added dropwise to complete
Under be heated to reflux 15 hours.It is cooled to room temperature after reaction, adjusts solution ph to 2 or so with concentrated hydrochloric acid, filter, gained is solid
Body is washed with acetone, and vacuum drying obtains faint yellow compound ii 2.51g, yield：84.7%, purity：98.12%.
Compound ii (10mmol, 2.96g) and 5mL boric acid are added in 100mL absolute ethyl alcohols, is heated to reflux 10 hours.
After reaction, rotation is evaporated ethyl alcohol, obtained solid successively with 5% sodium carbonate liquor, be washed to neutrality, then washed with acetone,
Vacuum drying, obtains III 3.15g of yellow compound, yield：89.4%, purity：99.26%.
Compound III (10mmol, 3.52g), constant pressure under conditions of being heated to reflux are added in 100mL anhydrous acetonitriles
20mL hydrazine hydrates are slowly added dropwise in funnel, and the reaction was continued 10 hours after being added dropwise to complete.It is cooled to room temperature, will react after reaction
Liquid pours into the water of 100mL, is then extracted with ethyl acetate (50mL × 3), merges organic phase, and anhydrous magnesium sulfate is dried overnight,
Filtering obtains IV 2.94g of yellow compound, yield after rotating solvent evaporated：90.6%, purity：99.09%.
It is being passed through N2Under conditions of protection, compounds Ⅳ (10mmol, 3.24g) and different is added in 100mL dichloromethane
Thiocyanic acid phenyl ester (30mmol, 4.06g) reacts 48 hours at room temperature.Solvent evaporated is rotated after reaction, by obtained solid
Product crosses silicagel column (ethyl acetate:Hexane=1:3), crocus compound V (ddpb) 5.29g of solvent, production is evaporated off in rotation
Rate：89.0%, purity：98.16%.
Property section
1, absorption spectrum is tested
Anthraquinone derivative ddpb is to Hg2+Absorption spectrum identification
Fig. 1 is probe molecule ddpb to Hg2+Selective absorbing spectral matching factor.In a concentration of 0.1mmol/L probes of 10mL
Metal ion solution (the Al of 10 a concentration of 0.2mol/L of μ L (2 times of moles) is separately added into molecule ddpb solution3+、Ag+、Na+、Ca2+、Cd2+、Hg2+、Mg2+、Co2+、K+、Cu2+、Ni2+、Pb2+、Zn2+).Solution system used in experiment is acetonitrile/water
(1:1, v:V) mixed solution, absorption spectrum measure on Shimadzu UV-2450 type ultraviolet specrophotometers.
Probe molecule is in acetonitrile/water (1 as seen from Figure 1:1, v:V) absorption of itself is in 510nm in mixed solution
Left and right, after excessive metal ion is added into probe molecule solutions in we, it has been found that Hg only is being added2+Afterwards, solution
Absorption blue-shift to 465nm or so, the color of solution also becomes yellow from purple, and other when be added in probe molecule solutions
When metal ion, then without the generation of this phenomenon, this illustrates the absorption spectrum of the probe molecule to Hg2+There is unique sound
It answers.
Fig. 2 is Hg2+Figure is titrated to the absorption spectrum of probe molecule ddpb.It is molten in a concentration of 0.1mmol/L probes FcL of 10mL
The Hg of 0.2,0.4,0.6,0.8,1.0,1.2,1.4,1.6,1.8,2.0,2.5,3.0 times of mole is sequentially added in liquid2+.Experiment
Used in solution system be acetonitrile/water (1:1, v:V) mixed solution, absorption spectrum are ultraviolet in Shimadzu UV-2450 types
It is measured on spectrophotometer.As seen from Figure 2, with Hg2+Addition, the absorbing wavelength of solution is gradually blue shifted to by 510nm
465nm works as Hg2+After addition reaches 2 times of moles of probe molecule, the absorbing wavelength of solution no longer moves, and the rheobase at peak
This is constant.This illustrates probe molecule ddpb and Hg2+It is 1:2 coordinations.
2, fluorescence spectrum experiments
Anthraquinone derivative ddpb is to Hg2+Fluorescence identifying
Fig. 3 is probe molecule ddpb to Hg2+Selective fluorescence spectrum identification.Probe molecule ddpb is dissolved in acetonitrile/water
(1:1, v:V) in mixed solution, it is configured to the solution of a concentration of 10 μm of ol/L, is separately added into 2 times of moles in this solution
Metal ion (Al3+、Ag+、Na+、Ca2+、Cd2+、Hg2+、Mg2+、Co2+、K+、Cu2+、Ni2+、Pb2+、Zn2+).Excitation wavelength is
470nm measures the fluorescence spectrum of solution.From figure 3, it can be seen that there are one hypofluorescences to send out at 525nm for probe molecule solutions
Peak is penetrated, Hg is being added2+Afterwards, solution hypofluorescence emission peak at 525nm disappears, and occurs a very strong fluorescence at 582nm
Emission peak, and other metal ions are added then without this phenomenon, this illustrates the probe molecule to Hg2+It shows very strong glimmering
Light selects identity.Solution system used in experiment is acetonitrile/water (1:1, v:V) mixed solution, fluorescence spectrum exist
It is measured in 2 Fluorescence Spectrometer of AMINCO Bowman Series.
Fig. 4 is Hg2+To the fluorescence spectroscopic titration figure of probe molecule ddpb.In the second of the probe molecule ddpb of 10 μm of ol/L
Nitrile/water (1:1, v:V) in mixed solution, be separately added into 0.2,0.4,0.6,0.8,1.0,1.2,1.4,1.6,1.8,2.0,
2.5, the Hg of 3.0 times of moles2+.It is excited at 470nm, the emission spectrum of solution is measured, as shown in the figure with Hg2+Concentration
Increasing, hypofluorescence emission peak gradually weakens final disappearance at 525nm, and occurs a new fluorescence emission peak at 582nm, and
And in Hg2+The emission peak intensity that addition reaches after 2 times of moles at 582nm no longer increases substantially.
Fig. 5 is Hg2+With the probe molecule ddpb reaction time to the influence diagram of solution fluorescence intensity.In the probe of 10 μm of ol/L
The acetonitrile/water (1 of molecule ddpb:1, v:V) in mixed solution, the Hg of 2 times of moles is added2+.In excitation wavelength 470nm, hair
At the long 525nm of ejected wave, respectively at 0,1,2,3,4,5,6,7,8 minute recording solution fluorescence intensity.As shown, in probe
Hg is added in molecule ddpb solution2+After five minutes, fluorescence intensity reaches maximum value, and is held essentially constant as time went on.
Fig. 6 is when there is other coexistent metallic ions in solution to probe ddpb Selective recognitions Hg2+Influence diagram.10
The acetonitrile/water (1 of the probe molecule ddpb of μm ol/L:1, v:V) in mixed solution, it is separately added into the gold dissolved with 10 times of moles
Belong to ion (Al3+、Ag+、Na+、Ca2+、Cd2+、Hg2+、Mg2+、Co2+、K+、Cu2+、Ni2+、Pb2+、Zn2+), in excitation wavelength 470nm,
At launch wavelength 525nm, the fluorescence intensity of solution is measured, the Hg of 10 times of moles is then added in above-mentioned solution again2+, swashing
At hair wavelength 470nm, launch wavelength 525nm, the fluorescence intensity of solution is measured, from fig. 6 it can be seen that largely being deposited when in solution
In other metal ions, probe molecule ddpb is to Hg2+Selective recognition and unaffected.
Fig. 7 is Hg2+The linear relationship chart of concentration and fluorescence intensity.In the acetonitrile/water of the probe molecule ddpb of 1 μm of ol/L
(1:1, v:V) in mixed solution, it is separately added into the Hg of 0.1,0.2,0.3,0.4,0.5,0.6,0.7,0.8 times of mole2+
At excitation wavelength 470nm, launch wavelength 525nm, the fluorescence intensity of solution is measured.As can be seen from the figure when Hg2+ concentration exists
Good linear relationship (R2=0.9963) is showed within the scope of 0.1-0.8 μm of ol/L, obtained by 3 σ IUPAC criterion calculations
Detection is limited to 2.45 × 10-8mol/L。
Claims (8)
1. a kind of anthraquinone derivative, it is characterised in that：The structural formula of the derivative is as follows：
2. a kind of preparation method of anthraquinone derivative described in claim 1, it is characterised in that：
This approach includes the following steps：
1) chemical compounds I carries out oxidation reaction under the action of oxidant, and compound ii is prepared；
2) under acidic environment, compound ii carries out esterification with ethyl alcohol, obtains compound III；
3) under conditions of being heated to reflux, compound III is reacted with hydrazine hydrate, obtains compounds Ⅳ；
4) in the environment of inert gas shielding, compounds Ⅳ is reacted with phenyl isothiocyanate, obtains compound V.
3. preparation method according to claim 2, it is characterised in that：Oxidant described in step 1) be chromium trioxide,
Potassium permanganate or sodium hypochlorite；Solvent used in oxidation reaction is ethyl alcohol or glacial acetic acid.
4. preparation method according to claim 2, it is characterised in that：Acid reagent in step 2) used in acidic environment is
Sulfuric acid, phosphoric acid or boric acid, the temperature of esterification are to be heated to reflux temperature.
5. preparation method according to claim 2, it is characterised in that：Step 3) reaction solvent used is methanol, ethyl alcohol
Or acetonitrile.
6. preparation method according to claim 2, it is characterised in that：The temperature of step 4) reaction is 0~100 DEG C, reaction
Solvent used is methanol, ethyl alcohol, acetonitrile or dichloromethane.
7. application of the anthraquinone derivative described in claim 1 in terms of detecting mercury ion.
8. application according to claim 7, it is characterised in that：The anthraquinone derivative detects mercury ion in the environment
Using.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810947510.8A CN109096166B (en) | 2017-12-27 | 2017-12-27 | Preparation method of anthraquinone derivative |
| CN201810948071.2A CN108912025A (en) | 2017-12-27 | 2017-12-27 | A kind of anthraquinone derivative |
| CN201711439207.9A CN108164448B (en) | 2017-12-27 | 2017-12-27 | A kind of anthraquinone derivative and synthetic method and application |
| CN201810948057.2A CN109975254B (en) | 2017-12-27 | 2017-12-27 | Preparation method of anthraquinone derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711439207.9A CN108164448B (en) | 2017-12-27 | 2017-12-27 | A kind of anthraquinone derivative and synthetic method and application |
Related Child Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810948057.2A Division CN109975254B (en) | 2017-12-27 | 2017-12-27 | Preparation method of anthraquinone derivative |
| CN201810947510.8A Division CN109096166B (en) | 2017-12-27 | 2017-12-27 | Preparation method of anthraquinone derivative |
| CN201810948071.2A Division CN108912025A (en) | 2017-12-27 | 2017-12-27 | A kind of anthraquinone derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN108164448A CN108164448A (en) | 2018-06-15 |
| CN108164448B true CN108164448B (en) | 2018-10-09 |
Family
ID=62521702
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810948057.2A Expired - Fee Related CN109975254B (en) | 2017-12-27 | 2017-12-27 | Preparation method of anthraquinone derivative |
| CN201810947510.8A Expired - Fee Related CN109096166B (en) | 2017-12-27 | 2017-12-27 | Preparation method of anthraquinone derivative |
| CN201810948071.2A Pending CN108912025A (en) | 2017-12-27 | 2017-12-27 | A kind of anthraquinone derivative |
| CN201711439207.9A Expired - Fee Related CN108164448B (en) | 2017-12-27 | 2017-12-27 | A kind of anthraquinone derivative and synthetic method and application |
Family Applications Before (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810948057.2A Expired - Fee Related CN109975254B (en) | 2017-12-27 | 2017-12-27 | Preparation method of anthraquinone derivative |
| CN201810947510.8A Expired - Fee Related CN109096166B (en) | 2017-12-27 | 2017-12-27 | Preparation method of anthraquinone derivative |
| CN201810948071.2A Pending CN108912025A (en) | 2017-12-27 | 2017-12-27 | A kind of anthraquinone derivative |
Country Status (1)
| Country | Link |
|---|---|
| CN (4) | CN109975254B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109975254B (en) * | 2017-12-27 | 2021-05-04 | 南京晓庄学院 | Preparation method of anthraquinone derivative |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110669505B (en) * | 2019-11-19 | 2022-07-12 | 福建师范大学 | Preparation method and application of red fluorescence enhanced probe for detecting mercury ions |
| CN110922338B (en) * | 2019-12-20 | 2020-07-31 | 南京晓庄学院 | Anthraquinone derivative and synthesis method and application thereof |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101855324A (en) * | 2007-11-14 | 2010-10-06 | 巴斯夫欧洲公司 | The improvement of marker detects |
| CN102503875A (en) * | 2011-11-18 | 2012-06-20 | 厦门大学 | Fluorescent probe for detecting copper ions and preparation method thereof |
| CN102675164A (en) * | 2011-03-09 | 2012-09-19 | 同济大学 | Oligomerization sulfonate amino anthraquinone hypersensitive lead ion fluorescent probe, and preparation and application thereof |
| CN104610118A (en) * | 2015-02-21 | 2015-05-13 | 桂林理工大学 | Phenylthiourea derivative and application thereof |
| CN105352920A (en) * | 2015-10-08 | 2016-02-24 | 河南师范大学 | Method using 1,4-dihydroxy-9,10-anthraquinone thiosemicarbazone compound as fluorescent probe to detect copper ions |
| CN107245044A (en) * | 2017-07-07 | 2017-10-13 | 华南师范大学 | 2‑（Naphthylamino thioformyl）Hydrazine benzyl formate compound, synthetic method and application |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101496524B1 (en) * | 2012-12-17 | 2015-03-09 | 경북대학교 산학협력단 | detection method of mercury ion using 1,2-diaminoanthraquinone |
| CN106045878B (en) * | 2016-05-12 | 2017-11-03 | 山西大学 | A kind of anthraquinone derivative and its synthetic method and detection Cu2+In application |
| CN109975254B (en) * | 2017-12-27 | 2021-05-04 | 南京晓庄学院 | Preparation method of anthraquinone derivative |
-
2017
- 2017-12-27 CN CN201810948057.2A patent/CN109975254B/en not_active Expired - Fee Related
- 2017-12-27 CN CN201810947510.8A patent/CN109096166B/en not_active Expired - Fee Related
- 2017-12-27 CN CN201810948071.2A patent/CN108912025A/en active Pending
- 2017-12-27 CN CN201711439207.9A patent/CN108164448B/en not_active Expired - Fee Related
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101855324A (en) * | 2007-11-14 | 2010-10-06 | 巴斯夫欧洲公司 | The improvement of marker detects |
| CN102675164A (en) * | 2011-03-09 | 2012-09-19 | 同济大学 | Oligomerization sulfonate amino anthraquinone hypersensitive lead ion fluorescent probe, and preparation and application thereof |
| CN102503875A (en) * | 2011-11-18 | 2012-06-20 | 厦门大学 | Fluorescent probe for detecting copper ions and preparation method thereof |
| CN104610118A (en) * | 2015-02-21 | 2015-05-13 | 桂林理工大学 | Phenylthiourea derivative and application thereof |
| CN105352920A (en) * | 2015-10-08 | 2016-02-24 | 河南师范大学 | Method using 1,4-dihydroxy-9,10-anthraquinone thiosemicarbazone compound as fluorescent probe to detect copper ions |
| CN107245044A (en) * | 2017-07-07 | 2017-10-13 | 华南师范大学 | 2‑（Naphthylamino thioformyl）Hydrazine benzyl formate compound, synthetic method and application |
Non-Patent Citations (1)
| Title |
|---|
| 一种新型耐尔蓝衍生物的合成及其对Hg2+识别研究;徐鉴;《化学试剂》;20150228;158-161 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109975254B (en) * | 2017-12-27 | 2021-05-04 | 南京晓庄学院 | Preparation method of anthraquinone derivative |
Also Published As
| Publication number | Publication date |
|---|---|
| CN109975254B (en) | 2021-05-04 |
| CN108164448A (en) | 2018-06-15 |
| CN109975254A (en) | 2019-07-05 |
| CN109096166A (en) | 2018-12-28 |
| CN108912025A (en) | 2018-11-30 |
| CN109096166B (en) | 2020-02-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN108164448B (en) | A kind of anthraquinone derivative and synthetic method and application | |
| Tang et al. | Discovery of a sensitive Cu (II)-cyanide “off–on” sensor based on new C-glycosyl triazolyl bis-amino acid scaffold | |
| CN109232558B (en) | For detecting Cu2+Derivatives of (5) | |
| CN108658838B (en) | Heptamethine indocyanine-based formaldehyde fluorescent probe and preparation method and use method thereof | |
| CN113979998A (en) | Aluminum ion detection fluorescent probe based on 1, 8-naphthalimide as matrix and preparation method and application thereof | |
| CN110818734B (en) | Fluorescent probe with double-ratio recognition function for hydrogen peroxide and hypochlorous acid | |
| KR101105334B1 (en) | Compounds having AlIII ion selectivity and chemosensor using the same | |
| CN104326939B (en) | A kind of diaminomaleonitrile derivant and its preparation method and application | |
| CN105820811A (en) | Fluorescent probe, and synthesis method and application thereof | |
| CN104804466A (en) | Near-infrared outer squaraine dye modified with oxygen-ether chain as well as preparation method and application thereof | |
| CN111718276B (en) | Synthesis method of derivative | |
| CN108358815A (en) | A kind of Cu2+The preparation method and application of fluorescence probe | |
| CN113248430A (en) | Quinoline derivative-based fluorescence sensor, synthesis thereof and application thereof in aluminum ion detection | |
| CN110551499B (en) | Fluorescent probe for detecting copper ions and synthetic method thereof | |
| CN109575004B (en) | Preparation method of pyrazolyl coumarin schiff base copper ion fluorescent probe | |
| CN113603712B (en) | Preparation method of reactive fluorescent probe for rapid detection of hydrazine | |
| CN107216293B (en) | O-vanillin derivative and preparation method and application thereof | |
| CN110563702B (en) | Near-infrared fluorescent compound, preparation method and application thereof in detecting ferrous ions | |
| CN111747898B (en) | 2, 3-pindione imidazole type fluorescent probe for detecting hypochlorous acid and preparation method and application thereof | |
| CN113651741B (en) | Thiourea Schiff base, preparation method thereof and Zn serving as same 2+ 、Al 3+ Application of fluorescent probe | |
| CN111848602B (en) | Ratio type fluorescent probe for detecting magnesium ions, and preparation method and application thereof | |
| CN105820195A (en) | Ferrocenyl thiourea derivative as well as synthesis method and application | |
| CN117430551A (en) | Bimetallic ion fluorescent probe and preparation method thereof | |
| CN110790706A (en) | Molecular sensor capable of singly and selectively identifying picric acid molecules and synthesis and application thereof | |
| CN112410021A (en) | Supermolecule gel capable of performing single selective fluorescent recognition on arsenite ions and preparation and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for 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: 20181009 Termination date: 20211227 |
|
| CF01 | Termination of patent right due to non-payment of annual fee |