CN104292274A - Ferrocene naphthyridine derivative and preparation and application thereof - Google Patents
Ferrocene naphthyridine derivative and preparation and application thereof Download PDFInfo
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- CN104292274A CN104292274A CN201310302157.5A CN201310302157A CN104292274A CN 104292274 A CN104292274 A CN 104292274A CN 201310302157 A CN201310302157 A CN 201310302157A CN 104292274 A CN104292274 A CN 104292274A
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- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- -1 Ferrocene naphthyridine derivative Chemical class 0.000 title abstract description 10
- 230000000694 effects Effects 0.000 claims abstract description 12
- 238000000746 purification Methods 0.000 claims abstract description 3
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 claims description 39
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 12
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 8
- QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 230000007613 environmental effect Effects 0.000 abstract description 2
- 239000007788 liquid Substances 0.000 abstract 1
- BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical compound [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 description 31
- 239000000243 solution Substances 0.000 description 29
- 239000007864 aqueous solution Substances 0.000 description 24
- 238000001514 detection method Methods 0.000 description 19
- 238000001556 precipitation Methods 0.000 description 19
- 229910052753 mercury Inorganic materials 0.000 description 15
- 238000010521 absorption reaction Methods 0.000 description 14
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 13
- 230000008859 change Effects 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000002329 infrared spectrum Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 239000003153 chemical reaction reagent Substances 0.000 description 10
- UOFGSWVZMUXXIY-UHFFFAOYSA-N 1,5-Diphenyl-3-thiocarbazone Chemical compound C=1C=CC=CC=1N=NC(=S)NNC1=CC=CC=C1 UOFGSWVZMUXXIY-UHFFFAOYSA-N 0.000 description 9
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 230000003993 interaction Effects 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 230000000007 visual effect Effects 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 6
- 238000000141 square-wave voltammogram Methods 0.000 description 6
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 229910052742 iron Inorganic materials 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 238000006073 displacement reaction Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 229910021645 metal ion Inorganic materials 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
- 239000012346 acetyl chloride Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 238000004737 colorimetric analysis Methods 0.000 description 3
- 230000000536 complexating effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 229960000890 hydrocortisone Drugs 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000004365 square wave voltammetry Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- PJCCSZUMZMCWSX-UHFFFAOYSA-N 4,4-Dimethoxy-2-butanone Chemical compound COC(OC)CC(C)=O PJCCSZUMZMCWSX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 238000004847 absorption spectroscopy Methods 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 125000000879 imine group Chemical group 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000005054 naphthyridines Chemical group 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000003115 supporting electrolyte Substances 0.000 description 2
- 230000003313 weakening effect Effects 0.000 description 2
- 0 CC(C)(C=CC(C1=*C=C[C@]1(C)C(*)=O)=C)C(C)=O Chemical compound CC(C)(C=CC(C1=*C=C[C@]1(C)C(*)=O)=C)C(C)=O 0.000 description 1
- 244000124209 Crocus sativus Species 0.000 description 1
- SSQJVWMCDAVRGW-UHFFFAOYSA-N OC(C1=CCC=C1)=O Chemical compound OC(C1=CCC=C1)=O SSQJVWMCDAVRGW-UHFFFAOYSA-N 0.000 description 1
- 206010061481 Renal injury Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 206010044565 Tremor Diseases 0.000 description 1
- 238000002083 X-ray spectrum Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000009388 chemical precipitation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910001914 chlorine tetroxide Inorganic materials 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000005202 decontamination Methods 0.000 description 1
- 230000003588 decontaminative effect Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000002848 electrochemical method Methods 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000000724 energy-dispersive X-ray spectrum Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- ARRNBPCNZJXHRJ-UHFFFAOYSA-M hydron;tetrabutylazanium;phosphate Chemical compound OP(O)([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC ARRNBPCNZJXHRJ-UHFFFAOYSA-M 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000001095 inductively coupled plasma mass spectrometry Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 208000037806 kidney injury Diseases 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 150000001457 metallic cations Chemical class 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000001209 resonance light scattering Methods 0.000 description 1
- 238000002133 sample digestion Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
- C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic System
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/52—Treatment of water, waste water, or sewage by flocculation or precipitation of suspended impurities
- C02F1/54—Treatment of water, waste water, or sewage by flocculation or precipitation of suspended impurities using organic material
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/58—Treatment of water, waste water, or sewage by removing specified dissolved compounds
- C02F1/62—Heavy metal compounds
-
- 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
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/17—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
- G01N21/35—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry using infrared light
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/75—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
- G01N21/82—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 precipitate or turbidity
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- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N23/00—Investigating or analysing materials by the use of wave or particle radiation, e.g. X-rays or neutrons, not covered by groups G01N3/00 – G01N17/00, G01N21/00 or G01N22/00
- G01N23/22—Investigating or analysing materials by the use of wave or particle radiation, e.g. X-rays or neutrons, not covered by groups G01N3/00 – G01N17/00, G01N21/00 or G01N22/00 by measuring secondary emission from the material
- G01N23/223—Investigating or analysing materials by the use of wave or particle radiation, e.g. X-rays or neutrons, not covered by groups G01N3/00 – G01N17/00, G01N21/00 or G01N22/00 by measuring secondary emission from the material by irradiating the sample with X-rays or gamma-rays and by measuring X-ray fluorescence
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
- G01N27/26—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating electrochemical variables; by using electrolysis or electrophoresis
- G01N27/416—Systems
- G01N27/48—Systems using polarography, i.e. measuring changes in current under a slowly-varying voltage
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2101/00—Nature of the contaminant
- C02F2101/10—Inorganic compounds
- C02F2101/20—Heavy metals or heavy metal compounds
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Abstract
The invention relates to a ferrocene naphthyridine derivative and preparation and an application thereof. The novel ferrocene naphthyridine derivative designed and synthesized by the invention is high in production rate and low in cost, and can effectively identify and absorb Hg<2+> in a liquid, also has a recognition effect on Cu<2+>, and has a broad application prospect in environmental purification.
Description
Technical field
The present invention relates to a kind of ferrocene deriv and uses thereof, particularly a kind of have identify and purify the mercury ion aqueous solution and identify the ferrocene 7-naphthyridine derivatives of cupric ion and preparation thereof and purposes.
Background technology
Mercury has very strong inrichment, makes it to become one of harmful, the most dangerous heavy metal element, and its toxicity is very violent, can cause that finger trembles, kidney injury etc., and mercury metal has and converts organic mercury to and the tendency accumulated in vivo.Therefore how effectively to detect and remove mercury ion for all important in inhibiting in environmental science, bio-science and medical science.
At present, main method many employings cold atomic absorption of mercury ion standard, Pressurized sample digestion, dithizone light-intensity method, inductively coupled plasma mass spectrometry and Resonance Light Scattering Method is measured.These methods mainly all need expensive large-scale instrument and professional operator, and its cost is high, can not rapid detection.People are also very interested in the minimizing technology of mercury ion, report the method for various removal mercury ion up to now, mainly contain chemical precipitation method, absorption method, electrolytic process, metal deoxidization, ion exchange method, microbial method etc.
In host-guest chemistry, the molecular recognition performance of metallic cation is the focus of research always, and nitrogen-atoms, as one of heteroatoms modal in organic compound, is widely used in the design of host molecule.The introducing of multiple nitrogen-atoms in host compound, adds recognition site and reactive force, makes many nitrogen host molecule occupy critical role in host-guest chemistry research.
Existing detection mercury ion synthetic method all more complicated, production cost is expensive, and detection method is more complicated also, and not clearly, decontamination effect improving is poor for phenomenon.
Summary of the invention
An object of the present invention is to provide a kind of ferrocene 7-naphthyridine derivatives; Two of object of the present invention is the preparation method providing this ferrocene 7-naphthyridine derivatives a kind of; Three of object of the present invention is to introduce this ferrocene 7-naphthyridine derivatives in the application identifying purification mercury ion and cupric ion.
For achieving the above object, the present invention institute by the following technical solutions:
A kind of ferrocene 7-naphthyridine derivatives FecND, its chemical structural formula is:
The preparation method of a kind of ferrocene 7-naphthyridine derivatives FecND, comprise: by ferrocene dicarboxylic acid at HBTU, DIPEA(Chinese name: N, N-diisopropylethylamine) effect under, with 2-amino-7-methyl isophthalic acid, 8-naphthyridines is obtained by reacting novel ferrocene deriv FecDN.
Reaction process is as follows:
As preferred Scheme, the preparation scheme of described ferrocene dicarboxylic acid is: diacetyl ferrocene reacts to obtain ferrocene dicarboxylic acid with bromine in the basic conditions.
Reaction process is as follows:
As preferred scheme, the preparation scheme of described diacetyl ferrocene is: the dichloromethane solution of ferrocene and Acetyl Chloride 98Min. is obtained by reacting diacetyl ferrocene under the effect of aluminum chloride.
Reaction process is as follows:
As preferred scheme, described 2-amino-7-methyl isophthalic acid, the preparation scheme of 8-naphthyridines is: DAP and 4,4-dimethoxy-butanone are added in phosphoric acid and be obtained by reacting 2-amino-7-methyl isophthalic acid at 98 DEG C, 8-naphthyridines.
Reaction process is as follows:
Present invention further teaches the purposes of ferrocene 7-naphthyridine derivatives FecND, namely it is at identification and or absorption Hg
2+, Cu
2+application.
Beneficial effect of the present invention is: 1) detection reagent ferrocene naphthyridine compounds FecDN synthesizes simple, with low cost; 2) utilize this detection reagent to detect mercury ion, method is simple, phenomenon is obvious, naked eyes can observe directly; 3) utilize this detection reagent to detect and can detect bivalent cupric ion, slightly deepen although only observe solution, its uv-vis spectra has and obviously changes; 4) this detection reagent also can be used as the mercury ion in precipitation agent purified aqueous solution simultaneously; 5) the present invention to mercury ion, cupric ion Visual retrieval and removal provide a kind of new reagent, environmental pollution and human health have very important meaning.
Accompanying drawing explanation
Fig. 1: the Visual retrieval dripping metal ion (final concentration is 5mM) in the ethanolic soln of FecDN (0.5mM);
Fig. 2: dropwise drip Hg
2+detect to the uv-vis spectra in 50 μ Μ FecDN ethanolic solns.Hg
2+change in concentration (along the direction of arrow): 0 μ Μ, 50 μ Μ, 100 μ Μ, 150 μ Μ, 200 μ Μ, 250 μ Μ, 300 μ Μ, 350 μ Μ, 400 μ Μ, 450 μ Μ, 500 μ Μ;
Fig. 3: dropwise drip Cu
2+detect to the uv-vis spectra in 50 μ Μ FecDN ethanolic solns, Cu
2+change in concentration (along the direction of arrow): 0 μ Μ, 50 μ Μ, 100 μ Μ, 150 μ Μ, 200 μ Μ, 250 μ Μ, 300 μ Μ, 350 μ Μ, 400 μ Μ, 450 μ Μ, 500 μ Μ;
The infrared spectra spectrogram of Fig. 4: FecDN (a) and FecDN-Hg (b);
The square wave voltammogram (SWV) of Fig. 5: FecDN.Dropwise drip Hg
2+be in 3:1 solution to 1m Μ FecDN ethanol and water volume ratio, [(n-Bu) 4] ClO4 is as supporting electrolyte.Hg
2+change in concentration in ethanolic soln is followed successively by: (along the direction of arrow): 0,0.1mM, 0.4mM, 0.7mM, 0.9mM, 1.2mM;
FecDN and B Fig. 6: A)) the EDX spectrum of FecDN-Hg;
Fig. 7: Hg in the mercury pollution aqueous solution
2+concentration be 10 μ Μ and 5 μ Μ, drip the Visual retrieval of FecDN;
Fig. 8: utilize UV/Vis spectrogram, dithizone detects FecDN to Hg in the aqueous solution
2+removal effect.FecDN is added drop-wise to 30 μ Μ Hg
2+in the aqueous solution, the change (along the direction of arrow) of the concentration of FecDN in water: from 0,15 μMs, 30 μMs, 60 μMs, 90 μMs, 120 μMs.
Embodiment
In order to make object of the present invention, technical scheme and advantage clearly understand, below in conjunction with drawings and Examples, the present invention is further elaborated.Should be appreciated that specific embodiment described herein only in order to explain the present invention, be not limited to the present invention.
First DAP (Beijing lark prestige science and technology) and 4,4-dimethoxy-butanone are added in phosphoric acid and be obtained by reacting 2-amino-7-methyl isophthalic acid at 98 DEG C, 8-naphthyridines.
Reaction process is as follows:
Ferrocene (production of Beijing lark prestige scientific & technical corporation) is obtained by reacting diacetyl ferrocene with the dichloromethane solution of Acetyl Chloride 98Min. under the effect of aluminum chloride.
Reaction process is as follows:
Diacetyl ferrocene reacts to obtain ferrocene dicarboxylic acid with bromine in the basic conditions.
Reaction process is as follows:
Then ferrocene dicarboxylic acid is under HBTU, DIPEA effect, and with 2-amino-7-methyl isophthalic acid, 8-naphthyridines is obtained by reacting novel ferrocene deriv FecDN.
Reaction process is as follows:
Single armed ferrocene 7-naphthyridine derivatives FecMN is prepared according to preparing the same method of ferrocene 7-naphthyridine derivatives, as follows:
Ferrocene Derivatives FecDN and FecMN of the present invention's synthesis passes through
1hNMR,
13c{H}NMR and MS means have carried out Structural Identification, confirm that its structure is indicated by above structural formula.
The ferrocene 7-naphthyridine derivatives that utilizes in the present invention carries out Visual retrieval (as Fig. 1) to mercury ion.From visual test result, solution turned cloudy add mercury ion in ferrocene 7-naphthyridine derivatives FecDN after, standing 1min has obvious orange solid precipitation.And as Mn after adding other ion
2+, Co
2+, Pb
2+, Cr
3+, Cr
2+, Cu
2+, Mg
2+, Ba
2+, Zn
2+solution state does not have considerable change.
Progressively drip different metal ion in the ethanolic soln of FecDN, detect the change of the uv-visible absorption spectroscopy before and after dripping.From detected result, along with the increase of the concentration of mercury ion, the absorption signal of the ultraviolet-visible detected also is weakening (as Fig. 2) thereupon.After dropping Cu2+, color has and slightly deepens, and UV-Visible absorption signal also there occurs obvious change (as Fig. 3), and adds after other ion as Mn
2+, Co
2+, Pb
2+, Cr
3+, Cr
2+, Mg
2+, Ba
2+, Zn
2+, the absorption signal of ultraviolet-visible does not have considerable change.
Compare (Fig. 4) the detection that compound F 17-hydroxy-corticosterone ecDN and throw out (FecDN-Hg) have carried out infrared spectra in the present invention, can find out that their infrared spectra there occurs larger change, the infrared spectrogram medium wave numerical value of compound F 17-hydroxy-corticosterone ecDN is 3400cm
-1the characteristic peak that left and right goes out, at complexing Hg
2+after, there occurs displacement, illustrate that the atom N on imine group take part in coordination.There is not obvious displacement in the specific peak absorbance peak that wave number value is less than 2000cm-1, can infer, the atom N on naphthyridines ring does not probably participate in coordination.
Electrochemistry square wave voltammetry (SWV) is used to analyze FecDN and Hg in the present invention further
2+interaction (as Fig. 5).Result shows progressively to drip Hg
2+to detecting in solution (ethanolic soln of 1mMFecDN), oxidation peak current reduces thereupon, and spike potential does not move, when detection Hg solution
2+concentration and the concentration mol ratio of FecDN when reaching 1:1, the oxidation peak current completely dissolve at E=0.752V place.This may due to the generation of precipitation, and in solution, the amount of FecDN reduces gradually until be fully formed caused by precipitation.
Analyzed the content ratio (Fig. 6) of nitrogen in FecDN and FecDN-Hg, iron and mercury element by EDX simultaneously.EDX result shows, the measuring result of FecDN is, N:7.02%, Fe:1.02%, with standard value molar ratio (N:Fe=6:1) closely.The measuring result of FecDN-Hg is that the molar content of N, Fe, Hg is respectively: 9.15%, 1.43%, 1.97%, with standard value molar ratio (6:1:1) closely.Therefore, in the throw out FecDN-Hg formed, the atom number maximum possible ratio of N, Fe, Hg is 6:1:1, and namely FecDN and mercury ion are formed with the mol ratio of 1:1.Because this throw out is difficult to dissolve (as chloroform, DMF, DMSO etc.) in a lot of solvent, this throw out of our initial guess is a kind of complex polymer.
The above results illustrates that FecDN can identify mercury ion, and with obvious deposited phenomenon, and FecDN and mercury ion are formed with the mol ratio of 1:1.Because this throw out is difficult to dissolve (as chloroform, DMF, DMSO etc.) in a lot of solvent, we tentatively infer that this throw out is a kind of complex polymer.
Detection reagent FecDN solution to the detection of the mercury pollution aqueous solution, as shown in Figure 7, as Hg in the mercury pollution aqueous solution
2+concentration be 10 μ Μ, dripping detection reagent FecDN(final concentration is 10 μ Μ), occur significantly muddy, and have safran Precipitation after leaving standstill 1min.As Hg in the mercury pollution aqueous solution
2+concentration be 5 μ Μ, drip detection reagent FecDN, there is a small amount of muddiness, in 3 ~ 5 DEG C of standing 10min, a small amount of Precipitation that naked eyes can observe directly.
FecDN and Hg
2+interaction form precipitation, the object removing mercury ion in the mercury pollution aqueous solution can be reached, utilize dithizone colorimetric method in addition secondary proof in the present invention, as Fig. 8.Mercury ion can generate orange red complex compound with dithizone in an acidic solution, locates to produce new absorption peak in wavelength about 500nm.The ethanolic soln (5mM) of FecDN is progressively added dropwise to 30 μ Μ Hg after acidifying
2+the aqueous solution, filters.Get dithizone ethanolic soln to detect (Shimadzu2500UV/Vis) the mercury ion in filtrate.Carry out full wavelength scanner.30 μ Μ Hg after acidifying
2+the aqueous solution is blank.Result illustrates that FecDN has removal effect to mercury ion in the aqueous solution.
Embodiment 1: the synthesis and characterization of ferrocene 7-naphthyridine derivatives FecDN
In there-necked flask, add aluminum chloride 8.9738g/67.3mmol and the methylene dichloride 20ml of porphyrize, stirring and drip under frozen water cooling the dichloromethane solution of people's Acetyl Chloride 98Min. (6.7ml/94.2mmol), be stirred to aluminum chloride and substantially dissolve.And then add methylene dichloride (20ml) solution of ferrocene 5g/26.9mmol, drip to finish and stir lh prior to 10 DEG C after ice melts entirely, then release (about 3h) in stirring at room temperature to without hydrogenchloride.System goes on ice cube all melts to ice, separates organic phase, aqueous phase chloroform extraction with funnel, merges organic phase, successively with water and saturated sodium bicarbonate solution washing, and anhydrous sodium sulfate drying.Steaming desolventizes, and obtains thick product orange/yellow solid diacetyl ferrocene.Thick product is purified through silica column chromatography, with CHCl
3/ CH
3oH=50/1 is eluent, and productive rate is 68.8%.
Be dissolved in by sodium hydroxide 10g/0.25mol in 100mL water, 2ml bromine ice-water bath slowly drops to there-necked flask under stirring.Isosorbide-5-Nitrae-dioxane 18ml is dripped under vigorous stirring.Add ferrocene diethyl ketone 1.7557g/6.5mmol, vigorous stirring 2-3h under ice bath, solution becomes black, stopped reaction in batches.The filtrate of filtering, washing, it is colourless for being extracted to chloroform layer with water, separatory, and the HCl of water layer 6M is regulated PH=1-2, and occur a large amount of brown precipitate, suction filtration, vacuum-drying, obtain thick product ferrocene dicarboxylic acid, productive rate is 62.65%.
By ferrocene dicarboxylic acid (68.5mg, 0.25mmol), HBTU (568.8mg, 1.5mmol) and DIPEA (545mL, 2mmol) is dissolved in 10mLCH
2cl
2, stir-activating 1hr under ice bath.Then add 2-amino-7-methyl isophthalic acid, 8-naphthyridines (117.9mg, 0.75mmol), continue to stir under room temperature, by TLC detection reaction process, reaction in about 5 hours stops.Mixing solutions, after Rotary Evaporators evaporate to dryness, is dissolved in chloroform, uses saturated NaHCO respectively
3the aqueous solution and water washing, Na
2sO
4drying, filters, is spin-dried for and obtains FecDN crude product, be purified (R by column chromatography
f=0.5,30:1v/vCHCl
3/ CH
3oH), obtaining pure FecDN, is yellow solid 100.3mg, productive rate 72.14%.
1hNMR (CDCl
3, 600MHz) and δ: 2.75 (s, 6H), 4.60 (s, 4H), 4.96 (s, 4H), 7.23 (d, 2H, J=6Hz), 7.89 (d, 2H, J=12Hz), 7.97 (d, 2H, J=12Hz), 8.48 (d, 2H, J=12Hz), 8.62 (s, 2H).
13c{H}NMR (CDCl
3, 150MHz) and δ: 25.76,70.80,73.53,76.99,114.51,118.52,121.41,136.31,138.97,153.39,154.56,163.11,168.25.ESI-MScalculatedfor C
30h
24feN
6o
2[(M+H)
+] 557,13, found557.0.
Embodiment 2: Visual retrieval FecDN is to Hg
2+identification
Carry out FecDN and Hg
2+and the Visual retrieval of other ten kinds of common metal ion.By excessive Cr
3+, Mn
2+, Mg
2+, Cr
2+, Co
2+, Zn
2+, Cd
2+, Ba
2+, Pb
2+, Hg
2+and Cu
+the metal chloride aqueous solution be added dropwise in the ethanolic soln of 0.5mMFecDN, be added dropwise to Cr
3+, Mn
2+, Mg
2+, Cr
2+, Co
2+, Zn
2+, Cd
2+, Ba
2+, Pb
2+and Cu
+after, color and the state of solution significantly do not change.But be added dropwise to Hg
2+after, the obvious turbid phenomenon (as shown in Figure 1) that solution occurs, after leaving standstill the several seconds, has orange-yellow precipitation to occur, solution turned clear.These results demonstrate ferrocene 7-naphthyridine derivatives FecDN can Selective recognition mercury ion, and produces solid insoluble (we are designated as FecDN-Hg).
Embodiment 3: ultraviolet-visible absorption detects FecDN and different metal ionic interaction
Progressively drip metal ion in the ethanolic soln of single armed, ferrocene 7-naphthyridine derivatives, detect the change of the uv-visible absorption spectroscopy before and after dripping.From detected result, along with the increase of the concentration of mercury ion, the absorption signal of the ultraviolet-visible detected also is weakening (as Fig. 2) thereupon.Drip Cu
2+after, the absorption peak at 332nm place reduces, and the absorption peak at 210nm place increases gradually (as Fig. 3) gradually.And as Mn after adding other ion
2+, Co
2+, Pb
2+, Cr
3+, Cr
2+, Mg
2+, Ba
2+, Zn
2+, the absorption signal of ultraviolet-visible does not have considerable change.As can be seen here, FecDN also has recognition reaction to Cu2+.
Embodiment 4: infrared spectrum (IR) characterizes FecDN and Hg
2+interaction
By FecDN and Hg
2+infrared spectrogram (IR) before and after effect compares, and can find out that their IR spectrum there occurs larger change, as shown in Figure 4, curve a is the infrared spectra spectrogram of FecDN, and curve b is FecDN-Hg infrared spectra spectrogram.The infrared spectra spectrogram of FecDN-Hg compares, at 3406cm with the infrared spectra spectrogram of FecDN
-1the stretching vibration red shift of the N-H at place, N there occurs displacement after generation title complex, shows that the atom N on the imine group in part take part in coordination.And be less than 2000cm in wave number value
-1specific peak absorbance peak there is not obvious displacement, infer that the atom N on naphthyridines ring does not probably participate in coordination.
Embodiment 5: electrochemical Characterization FecDN and Hg
2+interaction
We utilize square wave voltammetry (SWV) to analyze FecDN and Hg
2+interaction.Amplitude be 25mV, frequency is 15Hz, potential range is 0.4 to 1.0V, and record SWV signal, TBAP is supporting electrolyte.The result of being tested by square wave voltammetry (SWV) draws (Fig. 5), and the oxidation peak current potential of compound F 17-hydroxy-corticosterone ecDN is at 0.752V place.Progressively drip Hg
2+to detecting in solution (ethanolic soln of 1mMFecDN), the oxidation peak current at E=0.752V place also reduces thereupon, when detection Hg solution
2+the concentration ≈ 1/1 of concentration/FecDN time, the oxidation peak current completely dissolve at E=0.752V place.Can be understood as, Hg
2+the ferrocene deriv FecDN detected in solution is progressively precipitated, the FecDN concentration detected in solution is gradually reduced, and then the characteristic peak of the ferrocene deriv FecDN at E=0.752V place also reduces thereupon, until disappear.
Embodiment 6: energy dispersion X-ray spectrum (EDX) characterizes FecDN and Hg
2+interaction
Application EDX analyzes the main component of FecDN and FecDN-Hg.The molecular formula of FecDN is C
30h
24feN
6o
2, the molecular formula of FecDN-Hg is (C
30h
24feN
6o
2hg
x) n.Due to the interference of many factors in detection, here we are only analyzed the content with N, Fe and Hg.EDX result shows that the measuring result of FecDN is, N:7.02%, Fe:1.02%, with standard value mol ratio (6:1) closely.The measuring result of FecDN-Hg is, N:9.15%, Fe:1.43%, Hg:1.97%, its mol ratio is about 6:1:1.Therefore, FecDN and Hg in precipitation FecDN-Hg is inferred
2+polymkeric substance is formed by 1:1 complexing.
Embodiment 7: detection reagent FecDN is to the detection of mercury ion in the aqueous solution
Detection reagent FecDN solution is added drop-wise in the aqueous solution of mercury pollution and goes, as shown in Figure 7, as Hg in the mercury pollution aqueous solution
2+concentration be 10 μ Μ, dripping FecDN(final concentration is 10 μ Μ), occur significantly muddy, and have Precipitation after leaving standstill 1min.As Hg in the mercury pollution aqueous solution
2+concentration be 5 μ Μ, dripping FecDN(final concentration is 20 μ Μ), there is a small amount of muddiness, in 3 ~ 5 DEG C of standing 10min, a small amount of Precipitation that naked eyes can observe directly.Continue to reduce Hg in the mercury pollution aqueous solution
2+concentration to 1 μ Μ (5mL), drip FecDN (final concentration is 1 μ Μ), not there is muddiness in shake well, cooling leave standstill after visual inspection less than obvious precipitation, may due to precipitation capacity very little.If after the water in solution being evaporated 4mL here, be observed visually precipitation and produced.Continue to reduce Hg in the mercury pollution aqueous solution
2+concentration to 0.1 μ Μ (10mL), drip FecDN (final concentration is 0.1 μ Μ), not there is muddiness in shake well, cooling leave standstill does not observe precipitation yet, after equally the water in solution being evaporated 9mL, be observed visually precipitation.Really be the precipitation that FeDN and mercury ion complexing generate to verify, same volume has respectively been carried out identical process with the FecDN solution of solvent with mercury ion solution with concentration by us, do not find that precipitation produces, therefore steam the water detected in solution to facilitate that to observe precipitation be feasible.
Embodiment 8:FecDN is to the removal effect of mercury ion in the aqueous solution
Here we utilize classical dithizone colorimetric method to demonstrate the removal effect of ferrocene deriv FecDN to mercury ion in the aqueous solution.Mercury ion can generate orange red complex compound with dithizone in an acidic solution, locates to produce new absorption peak in wavelength about 500nm.The Hg of pH=4 ~ 5 is added dropwise to the ethanolic soln of 5mMFecDN
2+the aqueous solution (30 μ Μ), filters and utilizes dithizone colorimetric method to carry out mercury ion detecting to filtrate.After the ethanolic soln getting 15 μ L6mM dithizones adds filtrate, by Shimadzu2500UV/Vis, detect ultra-violet absorption spectrum respectively.Carry out full wavelength scanner.From the result (Fig. 8) detected, along with the increase of FecDN add-on, then Hg
2+generate with dithizone the absorption that orange red complex compound locates to produce in wavelength about 500nm to weaken gradually.As can be seen here, FecDN really can be formed with mercury ion and precipitate and the mercury ion removed in the aqueous solution.
Claims (4)
1. a ferrocene 7-naphthyridine derivatives FecND, its chemical structural formula is:
。
2. the preparation method of a ferrocene 7-naphthyridine derivatives FecND, comprise: by ferrocene dicarboxylic acid at HBTU, DIPEA(Chinese name: N, N-diisopropylethylamine) effect under, with 2-amino-7-methyl isophthalic acid, 8-naphthyridines is obtained by reacting novel ferrocene deriv FecDN.
3. ferrocene 7-naphthyridine derivatives FecND is at identification and or purification Hg
2+application.
4. ferrocene 7-naphthyridine derivatives FecND is at identification Cu
2+application.
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| CN105806794A (en) * | 2016-05-17 | 2016-07-27 | 苏州大学 | 2-mercaptobenzothiazole as Cu2+And Hg2+Use of colorimetric probes |
| CN107121464A (en) * | 2017-05-03 | 2017-09-01 | 湖北大学 | A kind of magnetic dual-functional nanometer probe and its preparation method and application |
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