CN101747332A - Quinacridone derivatives containing urea bonds and gels thereof - Google Patents
Quinacridone derivatives containing urea bonds and gels thereof Download PDFInfo
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- CN101747332A CN101747332A CN200910218088A CN200910218088A CN101747332A CN 101747332 A CN101747332 A CN 101747332A CN 200910218088 A CN200910218088 A CN 200910218088A CN 200910218088 A CN200910218088 A CN 200910218088A CN 101747332 A CN101747332 A CN 101747332A
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- gel
- urea key
- quinacridone derivative
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- quinacridone
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- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical class N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 239000004202 carbamide Substances 0.000 title claims abstract description 21
- 239000000499 gel Substances 0.000 title abstract description 36
- 239000003960 organic solvent Substances 0.000 claims abstract description 11
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 20
- 238000001816 cooling Methods 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000463 material Substances 0.000 abstract description 11
- -1 potassium phthalimidate Chemical compound 0.000 abstract description 6
- 238000004440 column chromatography Methods 0.000 abstract description 4
- 125000000524 functional group Chemical group 0.000 abstract description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 abstract description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 abstract description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 229960001701 chloroform Drugs 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 230000009471 action Effects 0.000 description 7
- 239000000084 colloidal system Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- 150000001793 charged compounds Chemical class 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- SGRHVVLXEBNBDV-UHFFFAOYSA-N 1,6-dibromohexane Chemical compound BrCCCCCCBr SGRHVVLXEBNBDV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 230000005311 nuclear magnetism Effects 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000002604 ultrasonography Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000005411 Van der Waals force Methods 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- GTQHJCOHNAFHRE-UHFFFAOYSA-N 1,10-dibromodecane Chemical compound BrCCCCCCCCCCBr GTQHJCOHNAFHRE-UHFFFAOYSA-N 0.000 description 1
- ZJJATABWMGVVRZ-UHFFFAOYSA-N 1,12-dibromododecane Chemical compound BrCCCCCCCCCCCCBr ZJJATABWMGVVRZ-UHFFFAOYSA-N 0.000 description 1
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical class CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 150000001719 carbohydrate derivatives Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
Abstract
The invention belongs to the technical field of organic photoelectric material and particularly relates to four quinacridone derivative luminescent materials containing urea bond functional groups and gels thereof. The structural formula of the luminescent material is shown as follows, wherein n is 6, 8, 10 or 12, and the luminescent material is obtained through the following steps: DCBn reacts with potassium phthalimidate in DMF to obtain DUPn, a pure product is obtained through simple column chromatography, a protection group is separated in solution with hydrazine hydrate as alkaline environment to form end amino, and the product directly reacts with cyanate. The luminescent material can obtain stable gel in the organic solvent and reflects stronger yellow green fluorescence emission.
Description
Technical field
The invention belongs to the organic photoelectrical material technical field, be specifically related to four kinds and contain the quinacridone derivative luminescent material of urea key functional group and the gel of formation thereof.
Background technology
In recent years, it is found that some small molecules solution of organic compound can (even being lower than 1wt%) make the organic solvent gelation under very low concentration, become organogel, or claim molecular gel.This class organic compound is called as the gel factor.The gel factor can spontaneously be assembled in solvent, is assembled into ordered structure, and then makes whole system gelation.Its preparation method be with the gel factor in the organic solvent heating for dissolving, be cooled to room temperature again.Intermolecular by formation three-dimensional network systems such as hydrogen bond action, Van der Waals force, hydrophobic interaction and π-π interact.Wherein, the stimuli responsive gel more becomes the focus that people pay close attention to.Molecular gel environmental change to external world comprises light, heat, enzyme, magnetic, redox, and ion etc. makes some responses, but very rare for the report of ultrasonic response gel, and therefore the functional molecular that has a superior assembling performance for effective design must be understood in depth its gel mechanism.
According to causing that gel factor accumulative reactive force difference can be divided into the gel factor two classes: the hydrogen bond action gel factor and the non-hydrogen bond action gel factor.The gel factor of hydrogen bond action comprises fatty acyl amide, and based on the hexahydroaniline of urea groups, contract amino acid and carbohydrate derivative, they form the fibrous or helicoidal structure of specific unidimensional in organic solvent.The gel factor of non-hydrogen bond action mainly is the courage steroid derivatives, and the reactive force of this compounds mainly is π-π interaction, Van der Waals force and hydrophobic interaction etc.
Quinacridone (quinacridone, QA) full name is quino-[2,3-b]-acridine-5,12-dihydro-7, the 14-diketone (5,12-Dihydro-quino[2,3-b] acridone-7,14-dione), nineteen thirty-five is at first synthetic by H.Liebermann.Because it has good light, heat and chemical stability, be orange, the red colour system dyestuff of a class excellent performance therefore.The whole molecule of quinacridone molecule has the big π key of height conjugated and can form two dimensional structure, makes it include organic electroluminescence devices as organic photoelectrical material, and solar cell, field-effect transistor have obtained to use widely.For the supramolecule assembling aspect of quinacridone derivative also by people's extensive concern, from the research three-dimensional crystalline structure, the quinacridone compound has been showed enchanting charm and huge potentiality to be exploited in two-dimensional film and one-dimensional micro-nanometer material assembling field.
Based on the research basis to the photophysical property of quinacridone derivative and assembling character, we introduce this simple hydrogen bond action group of urea key to it, the synthesizing new functional organic molecule, and the further investigation external environment is to the influence of its supramolecule assembling character.
Summary of the invention
The purpose of this invention is to provide four kinds of urea key functional group quinacridone luminescent material and gels thereof with supramolecule colloidal property, be called for short DUCn (n=6 below, 8,10,12), and to ultrasonic wave, heat and solvent to its supramolecule assembling character, mechanism, and the influence of photophysical property is furtherd investigate.
Of the present invention to liking Compound D UCn (n=6,8,10,12), the preparation method of compound is as follows:
Reaction conditions: i) positive two bromo alkane, sodium hydride, Tetrabutyl amonium bromide, tetrahydrofuran (THF); Ii) n-Butyl Amine 99, tetrahydrofuran (THF); Iii) courage steroid acyl chlorides, triethylamine, methylene dichloride.
Compound D CBn is according to document Chem.Commun.; 2001; 561-562 report method is synthetic; DUPn directly reacts in DMF by DCBn and potassium phthalimide and makes; obtain clean product through simple column chromatography; in the solution of hydrazine hydrate, slough blocking group and form the end bit amino as alkaline environment, then product directly and polyisocyanate reactant obtain target product.Compound D UCn synthetic method is simple, and simple molecular configuration can help studying its supramolecule assembling character.
The quinacridone luminescent material that contains urea key functional group of the present invention, its structural formula is as follows:
Wherein, n=6,8,10 or 12.
The quinacridone derivative gel that contains the urea key, it is that the foregoing quinacridone derivative that contains the urea key is dissolved in organic solvent after heating, is positioned under the room temperature, forms gel after naturally cooling to room temperature; Or the foregoing quinacridone derivative that contains the urea key is dissolved in organic solvent after heating, and hot solution is carried out supersound process in the water of room temperature, obtain gel after placing for some time again.
The preceding described organic solvent of machine is methylene dichloride, trichloromethane, dimethyl formamide or chloroform etc.; The processing condition of supersound process are 0.4-1.5 watt/square centimeter, 20-80 kilohertz, 10-60 second, place after 10-30 minute again and obtain gel.
We at methylene dichloride, are research object with Compound D UC6 in trichloromethane and the dimethyl formamide, and its stimuli responsive gelling properties is discussed.
DUC6 can form stable colloid at methylene dichloride hot solution naturally cooling, and naturally cooling forms block precipitation in dimethyl formamide, and to its hot solution through cooling off then (0.45 watt/square centimeter of ultrasound procedure fast, 40 kilohertzs, 10 seconds) after can form stable gel, colloidal state all shows stronger yellow green fluorescence emission.We carry out characterization research to this phenomenon, below it are made explanations.
Utilizing the nuclear-magnetism characterization method that the colloid in two individual system is formed mechanism studies.DUC6 concentration along with gel molecular in trichloromethane increases gradually, the aromatic nucleus nuclear magnetic signal moves to High-Field gradually, and the urea key signals moves to low gradually, explanation increases with concentration, π-the π of intermolecular quinacridone nuclear and the hydrogen bond action power of urea key play effect gradually, cause the nuclear magnetisation displacement study.When the alternating temperature nuclear-magnetism was presented at 325K, the chloroform soln of DUC6 obtained the very strong nuclear magnetic spectrum of signal, was reduced in gradually with temperature to form in the colloidal process, and the urea key signals moves to low field gradually, illustrates that the hydrogen bond of urea key plays an important role in colloid.The DMF solution alternating temperature nuclear-magnetism of DUC6 also demonstrates similar nuclear magnetic signal variation tendency, the hydrogen bond that has also proved the urea key plays effect, it should be noted that and two new signals between 6-7ppm, occur, the chloroform system of this and front is different, and raise gradually with temperature, these two signals weaken gradually and shift to High-Field, there are certain reactive force in explanation solvent and solute molecule in solution, induce part urea key to shift to low, and with the temperature rising, this class reactive force weakens gradually weakens up to disappearance this part signal gradually.This also can explain in DMF the principle that forms ultrasound gel: during naturally cooling because exist the effect of solvent solute molecule to cause gel molecular that orderly accumulation can not take place, thereby form a large amount of precipitations, ultrasonic when system is carried out, ultrasonic wave can be destroyed solvent solute molecule reactive force and cause gel molecular to take place to pile up in order and the formation stable gel.
We utilize synthetic new function quinacridone gel molecular to study its assembling character in solution, and obtain ultrasonic wave, and heat and solvent are to the assembling performance impact of molecular gel, and this provides actual foundation to further investigation design new function organic colloid.
Description of drawings
Fig. 1: the scanning electronic microscope of DUC6/ methylene dichloride xerogel;
Fig. 2: the scanning electronic microscope of DUC6/ dimethyl formamide (DMF) xerogel.
The colloid that the DCC6 gel forms after ultrasonic 10 seconds is drained in the freezing vacuum down of liquid nitrogen (77K) and is obtained xerogel.
As shown in Figure 1, the xerogel in methylene dichloride and DMF all is three-dimensional network-like structures, and fiber size is about about 50nm, and sends fluorescent orange.
Embodiment
Embodiment 1: Compound D UC6's is synthetic
Under the nitrogen protection condition; DCB6 (2.55 gram); 60 ℃ of heating of dimethyl formamide solution (100 milliliters) of sodium iodide (0.5 gram) and potassium phthalimide (2.96 gram) 24 hours; cooling; add 200 ml water termination reactions; the solid that obtains is carried out column chromatography for separation (silica gel, trichloromethane) obtain orange DUP6 target product 2.70 grams (88%).
DUP6 (0.90 gram) and hydrazine hydrate (5.0 milliliters) refluxed 5 hours in 90 milliliters of tetrahydrofuran (THF)/ethanol=1: 1 (volume/volume), and decompression steams organic solvent, adds 100 ml water suction filtrations, dries obtaining filter cake.Solid is obtained target product DUN6 (0.54 gram, 90%) with trichloromethane and hexanaphthene recrystallization.
DUN6 (0.4 gram) joins in the solution of 50 milliliters of hexyl isocyanic ester (0.24 gram) in 30 milliliters of chloroform/methanol=1: 1 (volume/volume), stirred overnight at room temperature.Underpressure distillation goes out organic solvent, solid is carried out column chromatography (silica gel, trichloromethane) obtain orange target product DUC6 (0.54 gram, 91%).Mass spectrum molecular ion peak: 765.2.Ultimate analysis is according to chemical formula C
46H
64N
6O
4Calculate: C, 72.22%; H, 8.43%; N, 10.99%; O, 8.37%.Experimental value: C, 72.35%; H, 8.29%; N, 10.78%.
Embodiment 2: Compound D UC8's is synthetic
Compound D UC8's is synthetic the same with example 1, just when preparing DCBn with 1,8-two bromooctanes replacement 1,6-dibromo-hexane.Product D UC8 mass spectrum molecular ion peak: 820.8.Ultimate analysis is according to chemical formula C
50H
72N
6O
4Calculate: C:73.13%; H:8.84%; N:10.23%; O:7.79%.Experimental value: C:73.28%; H:8.79%; N:10.02%.
Embodiment 3: Compound D UC10's is synthetic
Compound D UC10's is synthetic the same with example 1, just when preparing DCBn with 1,10-dibromo-decane replacement 1,6-dibromo-hexane.Product D UC10 mass spectrum molecular ion peak: 877.2.Ultimate analysis is according to chemical formula C
54H
80N
6O
4Calculate: C:73.93%; H:9.19%; N:9.58%; O:7.30%.Experimental value: C:73.69%; H:9.35%; N:9.40%.
Embodiment 4: Compound D UC12's is synthetic
Compound D UC12's is synthetic the same with example 1, just when preparing DCBn with 1,12-dibromo-dodecane replacement 1,6-dibromo-hexane.Product D UC12 mass spectrum molecular ion peak: 933.9.Ultimate analysis is according to chemical formula C
58H
88N
6O
4Calculate: C:74.64%; H:9.50%; N:9.00%; O:6.86%.Experimental value: C:74.50%; H:9.60%; N:9.23%.
Embodiment 5: the preparation of gel
Be the preparation of example explanation gel below with Compound D UC6.DUC6 can form stable colloid at methylene dichloride hot solution naturally cooling, and naturally cooling forms block precipitation in dimethyl formamide, and to its hot solution through cooling off then (0.45 watt/square centimeter of ultrasound procedure fast, 40 kilohertzs, 10 seconds) after can form stable gel, colloidal state all shows stronger yellow green fluorescence emission.
Claims (3)
1. the quinacridone derivative that contains the urea key, its structural formula is as follows:
Wherein, n=6,8,10 or 12.
2. contain the quinacridone derivative gel of urea key, it is characterized in that: be that the described quinacridone derivative that contains the urea key of claim 1 is dissolved in organic solvent after heating, be positioned under the room temperature, form gel after naturally cooling to room temperature.
3. contain the quinacridone derivative gel of urea key, it is characterized in that: be that the described quinacridone derivative that contains the urea key of claim 1 is dissolved in organic solvent after heating, again hot solution carried out obtaining gel after the supersound process in the water of room temperature.
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| CN114230628A (en) * | 2021-12-27 | 2022-03-25 | 华东理工大学 | Quinacridone cholesterol compound and preparation method and application thereof |
| CN114230628B (en) * | 2021-12-27 | 2023-08-15 | 华东理工大学 | Quinacridone cholesterol compound and preparation method and application thereof |
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