CN103497189B - 1-hydroxyl-3,4:9,10-tetracarboxylic diimide and synthesis method as well as application thereof in measurement of fluorine content - Google Patents
1-hydroxyl-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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- CN103497189B CN103497189B CN201310470705.5A CN201310470705A CN103497189B CN 103497189 B CN103497189 B CN 103497189B CN 201310470705 A CN201310470705 A CN 201310470705A CN 103497189 B CN103497189 B CN 103497189B
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- tetracarboxylic acid
- perylene tetracarboxylic
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 239000011737 fluorine Substances 0.000 title claims abstract description 12
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 12
- 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
- 238000002360 preparation method Methods 0.000 claims description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical group CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 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
- 229940113088 dimethylacetamide Drugs 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 150000007942 carboxylates Chemical group 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 239000012188 paraffin wax Substances 0.000 claims description 2
- 235000017281 sodium acetate Nutrition 0.000 claims description 2
- 239000001632 sodium acetate Substances 0.000 claims description 2
- -1 halogen ions Chemical class 0.000 abstract description 7
- 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 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 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
- 238000000034 method Methods 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 230000002940 repellent Effects 0.000 description 3
- 239000005871 repellent Substances 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
- 238000004448 titration Methods 0.000 description 3
- 206010016818 Fluorosis Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 238000004847 absorption spectroscopy Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 208000004042 dental fluorosis Diseases 0.000 description 2
- 238000005516 engineering process Methods 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
- 238000003786 synthesis reaction Methods 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
- 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
- 238000013459 approach 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012496 blank sample Substances 0.000 description 1
- 238000007385 chemical modification 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
- 230000007812 deficiency Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000001514 detection method 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
- 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
- 229910052500 inorganic mineral Inorganic materials 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
- 150000001455 metallic ions Chemical group 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
- 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
- 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
- 238000012360 testing method 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
Classifications
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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
-
- 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"
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- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Immunology (AREA)
- Analytical Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Optics & Photonics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
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 fluoride, and prevent and treat with Drinking Water, carious tooth, osteoporotic clinical diagnosis and nerve gas, nuclear weapon uranium refinement etc. closely related.Fluorine is a kind of cumulative toxicant, and in animal and plant body, fluorinated volume exceedes and to a certain degree can cause fluorosis, has great importance during the therefore monitoring being determined at environmental fluoride pollution and endemic fluorosis of Oil repellent, evaluation and control control.
Detection method traditional at present comprises: volumetric analysis, Optical Analysis Method, colourimetry, the chromatography of ions, fluorine ion select electric level etc.Volumetric method be relatively accurately, simple and rapid analytical approach, but conventional thorium or zirconium, the titration of aluminium salt volumetric analysis are not obvious; Chromatography of ions color method is a kind of inorganic and liquid chromatography technology that is organic ion analyzed, and analyze while being very suitable for polycomponent and multielement, it is highly sensitive, selectivity good, and amount of samples is few, easily realizes robotization, but this equipment price is higher, is difficult to popularize; Fluoride ion selective electrode method has become the classical standard method measuring fluorinion concentration, fluoride ion selective electrode has good performance, good selectivity, is mainly used in the multiple fields such as the mensuration of fluorine gas in the mensuration of Oil repellent in the mensuration of fluorine in the mensuration of fluoride in water and inorganic solution, mineral material, organic or biological raw material and air.
Molecule absorption, fluorescence as transducing signal can reach Single Molecule Detection high sensitivity, can switch, can realize people and molecule communication, submicron had to visual sub-nano-space and differentiates and be that sub-millisecond is time-resolved, be widely used in the association areas such as biological chemistry, cell biology and analytical chemistry.Therefore design and synthesis easy easy-to-use, be swift in response, accurately the fluorine ion fluorescence chemical sensor of the characteristic such as sensitive be subject to people's attention always.
Perylene diimides has large conjugated pi system, it is closed electron deficient color development system, there is the aromatic compounds of intense fluorescence, there is excellent chemistry, light and heat chemical stability simultaneously, very strong absorption is had to the light of infrared region to visible range, fluorescence quantum yield is almost quantitative, and productive rate and life-span be not by the impact of oxygen.Yin Ci ， perylene diimides as a kind of signal element of excellent fluorescent probe molecule, through chemical modification, can utilize the optical characteristics of its excellence, can carry out selective enumeration method to predetermined substance.
Summary of the invention
The object of the invention is overcome above-mentioned deficiency and a kind of 1-hydroxyl-3,4:9,10-perylene tetracarboxylic acid diimides, its synthetic method and the application in fluorine content measurement are provided.
The technical scheme that the present invention takes is:
1-hydroxyl-3,4:9,10-perylene tetracarboxylic acid diimides, its structural formula is as follows:
Wherein, R
1for any alkyl, preferred fat alkyl, the further preferably straight chain of C1-8, branched paraffin or naphthenic hydrocarbon.
The preparation method of described 1-hydroxyl-3,4:9,10-perylene tetracarboxylic acid diimides, comprises step as follows:
By 1-NO
2-3,4:9,10-perylene tetracarboxylic acid diimides mixes with basic salt and is dissolved in polar organic solvent, described 1-NO
2the mass ratio of-3,4:9,10-perylene tetracarboxylic acid diimides and basic salt is 5-7:2-4, and the consumption of polar organic solvent is every gram of 1-NO
2-3,4:9,10-perylene tetracarboxylic acid diimides 40-50 milliliter; Heating, 40-80 DEG C of reaction 2-4 hour, obtains 1-OH-3,4:9,10-perylene tetracarboxylic acid diimides.
Described basic salt is carboxylate, carbonate or supercarbonate, preferred sodium acetate.
Described polar organic solvent is 1-METHYLPYRROLIDONE, N, N '-dimethyl formamide or N, N '-dimethyl acetamide, preferred 1-METHYLPYRROLIDONE.
Synthetic route of the present invention:
Note: M is metallic ion
R
1, R
2for any alkyl.
The described application of 1-hydroxyl-3,4:9,10-perylene tetracarboxylic acid diimides in fluorine content measurement.Application process is: joined by the solution of sample in the solution of 1-hydroxyl-3,4:9,10-perylene tetracarboxylic acid diimides, utilizes ultraviolet-visible spectrophotometry to survey 700-800nm absorption intensity, and contrast working curve tries to achieve the Oil repellent in sample.
The invention has the beneficial effects as follows:
(1) this compound is the noval chemical compound having no report, and single step reaction completes, the reaction time is short, reaction conditions is gentle, productive rate is high.(2) 1-OH-3,4:9,10-perylene tetracarboxylic acid diimides is to F in environment
-change have the change of very sharp absorption and fluorescence and not by the interference of other halide ions, can be realized it fluorine ion is detected.
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 ion environment;
Fig. 4 is 1 × 10
-5the dichloromethane solution of mol/L the compounds of this invention, adds tetrabutyl ammonium fluoride, tetrabutylammonium chloride, tetrabutyl ammonium bromide, tetrabutylammonium iodide respectively, makes halogen ion concentration be 2 × 10
-5photo during mol/L;
Fig. 5 is 1 × 10
-5the dichloromethane solution of mol/L the compounds of this invention, adds tetrabutyl ammonium fluoride, tetrabutylammonium chloride, tetrabutyl ammonium bromide, tetrabutylammonium iodide respectively, makes halogen ion concentration be 2 × 10
-5mol/L, the photo under 365nm uviol lamp.
Embodiment
Further illustrate below in conjunction with embodiment.
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 1-METHYLPYRROLIDONEs, are heated to 45 DEG C, react 3 hours, and cooling, is added dropwise to reactant liquor in the watery hydrochloric acid of 2mol/L, and separate out precipitation, suction filtration, washes 3 times, dry.Thick product carries out silica gel column chromatography, and leacheate is methylene chloride: ethyl acetate=20:1.Obtain N, N '-dicyclohexyl-1-OH-3,4:9,10-perylene tetracarboxylic acid diimides 400 milligrams, productive rate 70%.
Embodiment 2
Get 755 milligrams of N, N '-two (1,5-diisopropyl) phenyl-1-NO
2-3,4:9,10-perylene tetracarboxylic acid diimides and 400 milligrams of sal tartari are dissolved in 30 milliliters of N, N '-dimethyl formamide, are heated to 45 DEG C, react 3.5 hours, and cooling, is added dropwise to reactant liquor in the watery hydrochloric acid of 2mol/L, and separate out precipitation, suction filtration, washes 3 times, dry.Thick product carries out silica gel column chromatography, and leacheate is methylene chloride: ethyl acetate=20:1.Obtain N, N '-two (1,5-diisopropyl) phenyl-1-OH-3,4:9,10-perylene tetracarboxylic acid diimides 477 milligrams, productive rate 66%.
Embodiment 3
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, N '-dimethyl acetamide, are heated to 60 DEG C, react 2.5 hours, and cooling, is added dropwise to reactant liquor in the watery hydrochloric acid of 2mol/L, and separate out precipitation, suction filtration, washes 3 times, dry.Thick product carries out silica gel column chromatography, and leacheate is methylene chloride: ethyl acetate=20:1.Obtain N, N '-dicyclohexyl-1-OH-3,4:9,10-perylene tetracarboxylic acid diimides 389 milligrams, productive rate 68%.
Fluorine content measurement:
Product is made into 1 × 10
-5the dichloromethane solution of mol/L, adds tetrabutyl ammonium fluoride, tetrabutylammonium chloride, tetrabutyl ammonium bromide, tetrabutylammonium iodide respectively, makes halogen ion concentration be 2 × 10
-5mol/L.Ultraviolet-visible absorption spectroscopy, fluorescence spectrum test are carried out to the sample of the blank sample of product and interpolation halide ion.
Claims (6)
1.1-hydroxyl-3,4:9,10-perylene tetracarboxylic acid diimides, its structural formula is as follows:
Wherein, R
1for the straight chain of C1-8, branched paraffin or naphthenic hydrocarbon.
2. the preparation method of 1-hydroxyl-3,4:9,10-perylene tetracarboxylic acid diimides according to claim 1, is characterized in that, comprise step as follows: by 1-NO
2-3,4:9,10-perylene tetracarboxylic acid diimides mixes with basic salt and is dissolved in polar organic solvent, described 1-NO
2the mass ratio of-3,4:9,10-perylene tetracarboxylic acid diimides and basic salt is 5-7:2-4, and the consumption of polar organic solvent is every gram of 1-NO
2-3,4:9,10-perylene tetracarboxylic acid diimides 40-50 milliliter; Heating, 40-80 DEG C of reaction 2-4 hour, obtains 1-OH-3,4:9,10-perylene tetracarboxylic acid diimides; Described basic salt is carboxylate, carbonate or supercarbonate.
3. the preparation method of 1-hydroxyl-3,4:9,10-perylene tetracarboxylic acid diimides according to claim 2, is characterized in that, described basic salt is sodium acetate.
4. the preparation method of 1-hydroxyl-3,4:9,10-perylene tetracarboxylic acid diimides according to claim 2, is characterized in that, described polar organic solvent is 1-METHYLPYRROLIDONE, N, N '-dimethyl formamide or N, N '-dimethyl acetamide.
5. the preparation method of 1-hydroxyl-3,4:9,10-perylene tetracarboxylic acid diimides according to claim 4, is characterized in that, described polar organic solvent is 1-METHYLPYRROLIDONE.
6. the application of 1-hydroxyl-3,4:9,10-perylene tetracarboxylic acid diimides according to claim 1 in fluorine content measurement.
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| CN104101577B (en) * | 2014-08-05 | 2017-07-14 | 贵州大学 | A kind of method that ratio absorption spectrophotometry determines Ag+ or F |
| EP3320329A4 (en) | 2015-07-09 | 2019-02-13 | University of Utah Research Foundation | Sensor compounds and associated methods and devices |
| 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 |
| CN105541839B (en) * | 2016-02-05 | 2018-03-23 | 山东师范大学 | Single tetracarboxylic acid diimide of nitro monoamideization 3,4,9,10 and preparation method thereof |
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| 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 |
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