CN103497189A - 1-OH-3,4:9,10-tetracarboxylic diimide and synthesis method as well as application thereof in measurement of fluorine content - Google Patents
1-OH-3,4:9,10-tetracarboxylic diimide and synthesis method as well as application thereof in measurement of fluorine content Download PDFInfo
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- CN103497189A CN103497189A CN201310470705.5A CN201310470705A CN103497189A CN 103497189 A CN103497189 A CN 103497189A CN 201310470705 A CN201310470705 A CN 201310470705A CN 103497189 A CN103497189 A CN 103497189A
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- tetracarboxylic acid
- perylene tetracarboxylic
- acid diimides
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- tetracarboxylic diimide
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 239000011737 fluorine Substances 0.000 title claims abstract description 17
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 17
- 238000005259 measurement Methods 0.000 title claims abstract description 7
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 title abstract 6
- 229910000071 diazene Inorganic materials 0.000 title abstract 6
- 238000001308 synthesis method Methods 0.000 title abstract 3
- 150000001447 alkali salts Chemical class 0.000 claims abstract description 8
- 239000003495 polar organic solvent Substances 0.000 claims abstract description 8
- -1 halogen ions Chemical class 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical group CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical group [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 235000017281 sodium acetate Nutrition 0.000 claims description 2
- 239000001632 sodium acetate Substances 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 238000010521 absorption reaction Methods 0.000 abstract description 5
- 229910052736 halogen Inorganic materials 0.000 abstract description 4
- 150000002500 ions Chemical class 0.000 abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 7
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 6
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 6
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 3
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 3
- 238000000207 volumetry Methods 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 238000004847 absorption spectroscopy Methods 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 206010016818 Fluorosis Diseases 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 229910052776 Thorium Inorganic materials 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 159000000013 aluminium salts Chemical class 0.000 description 1
- 229910000329 aluminium sulfate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000012496 blank sample Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003759 clinical diagnosis Methods 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 208000004042 dental fluorosis Diseases 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 230000007860 molecular communication Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000003958 nerve gas Substances 0.000 description 1
- 238000004204 optical analysis method Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000001009 osteoporotic effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000004557 single molecule detection Methods 0.000 description 1
- 235000011091 sodium acetates Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 230000002463 transducing effect Effects 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-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
- G01N21/17—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
- G01N21/33—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry using ultraviolet 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
- G01N21/62—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"
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- Optics & Photonics (AREA)
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Abstract
The invention relates to 1-OH-3,4:9,10-tetracarboxylic diimide and a synthesis method as well as an application thereof in measurement of fluorine content. The synthesis method comprises the following step: mixing and dissolving 1-NO2-3,4:9,10-tetracarboxylic diimide and a basic salt in a polar organic solvent for reacting for 2 to 4 hours within 40 DEG C to 80 DEG C, thereby obtaining 1-OH-3,4:9,10-tetracarboxylic diimide. The 1-OH-3,4:9,10-tetracarboxylic diimide has very acuminous absorption and fluorescence changes on the changes of F<-> in an environment and cannot be affected by other halogen ions. Therefore, the 1-OH-3,4:9,10-tetracarboxylic diimide can be used for detecting F (fluorine) ions.
Description
Technical field
The present invention relates to 1-hydroxyl-3,4:9,10-perylene tetracarboxylic acid diimides, its synthetic method and application, belong to technical field of organic synthesis.
Background technology
Fluorine is one of trace element of needed by human, it is distributed widely in the whole middle natures such as soil, water and animals and plants with the form of fluorochemical, and closely related with the uranium refinement of the control of Drinking Water, carious tooth, osteoporotic clinical diagnosis and nerve gas, Nuclear weapons etc.Fluorine is a kind of cumulative toxicant, and the interior fluorine content of animal and plant body surpasses to a certain degree can cause fluorosis, so has great importance in the monitoring that is determined at environmental fluoride pollution and endemic fluorine poisoning of fluorine content, evaluation and control control.
Traditional detection method comprises at present: volumetry, Optical Analysis Method, colorimetry, ion chromatography, fluorion are selected electricity level etc.Volumetry be relatively accurately, simple and rapid analytical procedure, but thorium commonly used or zirconium, the titration of aluminium salt volumetry are not obvious; The chromatography of ions color method is a kind of inorganic and liquid chromatography technology organic ion of analyzing, and when being very suitable for polycomponent and multielement, analyzes, and it is highly sensitive, selectivity good, and amount of samples is few, easily realizes automatization, but this equipment price is higher, is difficult to popularize; Fluoride ion selective electrode method has become the classical standard method of measuring fluorinion concentration, fluoride ion selective electrode has good performance, good selectivity, be mainly used in the multiple fields such as mensuration of fluorine gas in the mensuration of fluorine content in the mensuration of fluorine in the mensuration, mineral material of fluorochemical in water and inorganic solution, organic or biological raw material and atmosphere.
But molecular absorption, fluorescence as transducing signal can reach Single Molecule Detection the high sensitivity switch, can realize people and molecule communication, submicron is had that visual inferior nano-space is differentiated and is that inferior millisecond is time-resolved, be widely used in the association areas such as biological chemistry, cytobiology and analytical chemistry.Therefore design synthetic easy easy-to-use, be swift in response, accurately the fluorion fluorescence chemical sensor of the characteristic such as sensitive is subject to people's attention always.
Perylene diimides has large conjugated pi system, it is the electron deficiency color development system of sealing, the aromatic compounds that intense fluorescence is arranged, there is excellent chemistry, light and heat chemical stability simultaneously, there is to very strong absorption visible region to the light of infrared region, fluorescence quantum yield is almost quantitatively, and productive rate and life-span are not subject to the impact of oxygen.Yin Ci ， perylene diimides can be used as a kind of signal element of good fluorescent probe molecule, through chemically modified, utilizes its excellent optical characteristics, can carry out the selectivity detection to predetermined substance.
Summary of the invention
The objective of the invention is to overcome above-mentioned deficiency and a kind of 1-hydroxyl-3 is provided, 4:9,10-perylene tetracarboxylic acid diimides, its synthetic method and the application in fluorine content measurement.
The technical scheme that the present invention takes is:
1-hydroxyl-3,4:9, the 10-perylene tetracarboxylic acid diimides, its structural formula is as follows:
Wherein, R
1for any alkyl, preferred fat alkyl, straight chain, branched paraffin or the naphthenic hydrocarbon of further preferred C1-8.
Described 1-hydroxyl-3,4:9, the preparation method of 10-perylene tetracarboxylic acid diimides comprises that step is as follows:
By 1-NO
2-3,4:9, the 10-perylene tetracarboxylic acid diimides mixes and is dissolved in polar organic solvent with basic salt, described 1-NO
2-3,4:9, the mass ratio of 10-perylene tetracarboxylic acid diimides and basic salt is 5-7:2-4, the consumption of polar organic solvent is every gram 1-NO
2-3,4:9,10-perylene tetracarboxylic acid diimides 40-50 milliliter; Heating, 40-80 ℃ of reaction 2-4 hour, obtain 1-OH-3,4:9,10-perylene tetracarboxylic acid diimides.
Described basic salt is carboxylate salt, carbonate or supercarbonate, preferably sodium acetate.
Described polar organic solvent is N-Methyl pyrrolidone, N, N '-dimethyl formamide or N, N '-N,N-DIMETHYLACETAMIDE, preferably N-Methyl pyrrolidone.
Synthetic route of the present invention:
Annotate: M is metal ion
R
1, R
2for any alkyl.
Described 1-hydroxyl-3,4:9, the application of 10-perylene tetracarboxylic acid diimides in fluorine content measurement.Application method is: the solution of sample is joined to 1-hydroxyl-3, and 4:9, in the solution of 10-perylene tetracarboxylic acid diimides, utilize ultraviolet-visible spectrophotometry to survey the 700-800nm absorption intensity, and the contrast working curve is tried to achieve the fluorine content in sample.
The invention has the beneficial effects as follows:
(1) this compound is the new compound that has no report, and single step reaction completes, the reaction times is short, reaction conditions is gentle, productive rate is high.(2) 1-OH-3,4:9, the 10-perylene tetracarboxylic acid diimides is to F in environment
-variation the variation of very sharp absorption and fluorescence is arranged and is not subject to the interference of other halide-ionss, can realize that it detects fluorion.
The accompanying drawing explanation
The proton nmr spectra of Fig. 1 embodiment of the present invention 1 compound;
The mass spectrum of Fig. 2 embodiment of the present invention 1 compound;
The ultraviolet-visible absorption spectroscopy of Fig. 3 the compounds of this invention in different halide-ions environment;
Fig. 4 is 1 * 10
-5the dichloromethane solution of mol/L the compounds of this invention, add respectively tetrabutyl ammonium fluoride, tetrabutylammonium chloride, Tetrabutyl amonium bromide, tetrabutylammonium iodide, and making halogen ion concentration is 2 * 10
-5photo during mol/L;
Fig. 5 is 1 * 10
-5the dichloromethane solution of mol/L the compounds of this invention, add respectively tetrabutyl ammonium fluoride, tetrabutylammonium chloride, Tetrabutyl amonium bromide, tetrabutylammonium iodide, and making halogen ion concentration is 2 * 10
-5mol/L, the photo under the 365nm ultraviolet lamp.
Embodiment
Below in conjunction with embodiment, further illustrate.
Embodiment 1
Get 600 milligrams of N, N '-dicyclohexyl-1-NO
2-3,4:9,10-perylene tetracarboxylic acid diimides and 200 milligrams of sodium acetates are dissolved in 30 milliliters of N-Methyl pyrrolidone, are heated to 45 ℃, react 3 hours, cooling, reaction solution are splashed in the dilute hydrochloric acid of 2mol/L, separate out precipitation, and suction filtration, wash 3 times, dries.Thick product carries out silica gel column chromatography, and leacheate is methylene dichloride: ethyl acetate=20:1.Obtain N, N '-dicyclohexyl-1-OH-3,4:9,400 milligrams of 10-perylene tetracarboxylic acid diimides, productive rate 70%.
Embodiment 2
Get 755 milligrams of N, N '-bis-(1,5-di-isopropyl) phenyl-1-NO
2-3,4:9,10-perylene tetracarboxylic acid diimides and 400 milligrams of salt of wormwood are dissolved in 30 milliliters of N, and N '-dimethyl formamide, be heated to 45 ℃, reacts 3.5 hours, cooling, reaction solution splashed in the dilute hydrochloric acid of 2mol/L, separates out precipitation, and suction filtration is washed 3 times, dries.Thick product carries out silica gel column chromatography, and leacheate is methylene dichloride: ethyl acetate=20:1.Obtain N, N '-bis-(1,5-di-isopropyl) phenyl-1-OH-3,4:9,477 milligrams of 10-perylene tetracarboxylic acid diimides, productive rate 66%.
Get 599 milligrams of N, N '-dicyclohexyl-1-NO
2-3,4:9,10-perylene tetracarboxylic acid diimides and 300 milligrams of saleratus are dissolved in 30 milliliters of N, and N '-N,N-DIMETHYLACETAMIDE, be heated to 60 ℃, reacts 2.5 hours, cooling, reaction solution splashed in the dilute hydrochloric acid of 2mol/L, separates out precipitation, and suction filtration is washed 3 times, dries.Thick product carries out silica gel column chromatography, and leacheate is methylene dichloride: ethyl acetate=20:1.Obtain N, N '-dicyclohexyl-1-OH-3,4:9,389 milligrams of 10-perylene tetracarboxylic acid diimides, productive rate 68%.
Fluorine content measurement:
Product is made into to 1 * 10
-5the dichloromethane solution of mol/L, add respectively tetrabutyl ammonium fluoride, tetrabutylammonium chloride, Tetrabutyl amonium bromide, tetrabutylammonium iodide, and making halogen ion concentration is 2 * 10
-5mol/L.Sample to the blank sample of product and interpolation halide-ions carries out ultraviolet-visible absorption spectroscopy, fluorescence spectrum test.
Claims (8)
1.1-hydroxyl-3,4:9, the 10-perylene tetracarboxylic acid diimides, its structural formula is as follows:
Wherein, R
1for any alkyl.
2. 1-hydroxyl-3 according to claim 1,4:9, the 10-perylene tetracarboxylic acid diimides, is characterized in that, described R
1choosing
Aliphatic group.
3. 1-hydroxyl-3 claimed in claim 1,4:9, the preparation method of 10-perylene tetracarboxylic acid diimides, is characterized in that, comprises that step is as follows: by 1-NO
2-3,4:9, the 10-perylene tetracarboxylic acid diimides mixes and is dissolved in polar organic solvent with basic salt, described 1-NO
2-3,4:9, the mass ratio of 10-perylene tetracarboxylic acid diimides and basic salt is 5-7:2-4, the consumption of polar organic solvent is every gram 1-NO
2-3,4:9,10-perylene tetracarboxylic acid diimides 40-50 milliliter; Heating, 40-80 ℃ of reaction 2-4 hour, obtain 1-OH-3,4:9,10-perylene tetracarboxylic acid diimides.
4. 1-hydroxyl-3 according to claim 3,4:9, the preparation method of 10-perylene tetracarboxylic acid diimides, is characterized in that, described basic salt is carboxylate salt, carbonate or supercarbonate.
5. 1-hydroxyl-3 according to claim 4,4:9, the preparation method of 10-perylene tetracarboxylic acid diimides, is characterized in that, described basic salt is sodium acetate.
6. 1-hydroxyl-3 according to claim 3,4:9, the preparation method of 10-perylene tetracarboxylic acid diimides, is characterized in that, described polar organic solvent is N-Methyl pyrrolidone, N, N '-dimethyl formamide or N, N '-N,N-DIMETHYLACETAMIDE.
7. 1-hydroxyl-3 according to claim 6,4:9, the preparation method of 10-perylene tetracarboxylic acid diimides, is characterized in that, described polar organic solvent is N-Methyl pyrrolidone.
8. 1-hydroxyl-3 claimed in claim 1,4:9, the application of 10-perylene tetracarboxylic acid diimides in fluorine content measurement.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104101577A (en) * | 2014-08-05 | 2014-10-15 | 贵州大学 | Ag+ or F- determining method by adopting rate absorption spectrophotometry |
| CN105541839A (en) * | 2016-02-05 | 2016-05-04 | 山东师范大学 | Mononitromonoamidated 3,4,9,10-perylene diimide and preparation method thereof |
| CN106350060A (en) * | 2015-07-17 | 2017-01-25 | 济南大学 | Reactive pH molecular probe as well as preparation method and application thereof |
| CN107850538A (en) * | 2015-07-09 | 2018-03-27 | 犹他大学研究基金会 | Sensor compound and associated method and apparatus |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101153848A (en) * | 2007-10-10 | 2008-04-02 | 吉林大学 | Fluorescent ion probe and its application in ion detecting |
| DE102006048638A1 (en) * | 2006-10-13 | 2008-04-17 | Langhals, Heinz, Prof. Dr. | New perylene dyes e.g. useful as pigments in inks, paints, lacquers and plastics |
-
2013
- 2013-10-10 CN CN201310470705.5A patent/CN103497189B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102006048638A1 (en) * | 2006-10-13 | 2008-04-17 | Langhals, Heinz, Prof. Dr. | New perylene dyes e.g. useful as pigments in inks, paints, lacquers and plastics |
| CN101153848A (en) * | 2007-10-10 | 2008-04-02 | 吉林大学 | Fluorescent ion probe and its application in ion detecting |
Non-Patent Citations (2)
| Title |
|---|
| YONGJUN LI，ET AL.，: "Synthesis and Self-Assembly of Dihydroxyperylene Bisimides for the Tuning of Photophysical Properties", 《CHEM. ASIAN J.》 * |
| 滕明爽 等: "萘酰亚胺衍生物荧光探针的研究进展", 《染料与染色》 * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104101577A (en) * | 2014-08-05 | 2014-10-15 | 贵州大学 | Ag+ or F- determining method by adopting rate absorption spectrophotometry |
| CN107850538A (en) * | 2015-07-09 | 2018-03-27 | 犹他大学研究基金会 | Sensor compound and associated method and apparatus |
| US11261181B2 (en) | 2015-07-09 | 2022-03-01 | University Of Utah Research Foundation | Sensor compounds and associated methods and devices |
| US11613537B2 (en) | 2015-07-09 | 2023-03-28 | University Of Utah Research Foundation | Sensor compounds and associated methods and devices |
| CN106350060A (en) * | 2015-07-17 | 2017-01-25 | 济南大学 | Reactive pH molecular probe as well as preparation method and application thereof |
| CN106350060B (en) * | 2015-07-17 | 2018-08-17 | 济南大学 | A kind of response type pH value molecular probe and preparation method and purposes |
| CN105541839A (en) * | 2016-02-05 | 2016-05-04 | 山东师范大学 | Mononitromonoamidated 3,4,9,10-perylene diimide and preparation method thereof |
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| Publication number | Publication date |
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| CN103497189B (en) | 2015-03-25 |
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