CN103194211B - Polymer ultraviolet fluorescent material used for anti-counterfeiting technology - Google Patents
Polymer ultraviolet fluorescent material used for anti-counterfeiting technology Download PDFInfo
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- CN103194211B CN103194211B CN201310059481.9A CN201310059481A CN103194211B CN 103194211 B CN103194211 B CN 103194211B CN 201310059481 A CN201310059481 A CN 201310059481A CN 103194211 B CN103194211 B CN 103194211B
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- 239000000463 material Substances 0.000 title claims abstract description 18
- 238000005516 engineering process Methods 0.000 title claims description 3
- 229920000642 polymer Polymers 0.000 title abstract description 24
- 239000000126 substance Substances 0.000 claims description 9
- -1 N-dialkyl amino Inorganic materials 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
- 150000007942 carboxylates Chemical group 0.000 claims description 3
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 238000004020 luminiscence type Methods 0.000 abstract description 7
- 238000002360 preparation method Methods 0.000 abstract description 4
- 229920000090 poly(aryl ether) Polymers 0.000 abstract description 3
- 229920000547 conjugated polymer Polymers 0.000 abstract 1
- 229920001002 functional polymer Polymers 0.000 abstract 1
- 239000002861 polymer material Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 28
- 150000001875 compounds Chemical class 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000003756 stirring Methods 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 238000001816 cooling Methods 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000004062 sedimentation Methods 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 230000006837 decompression Effects 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000000605 extraction Methods 0.000 description 6
- 0 C*(N(C(c(c1c2cc3)cccc1c3N(c1ccccc1)c1ccccc1)=O)C2=O)BrCc1cc(N(c2ccccc2)c(cc2)c(cccc3C([*+]4CCCCBr)=O)c3c2C4=O)ccc1 Chemical compound C*(N(C(c(c1c2cc3)cccc1c3N(c1ccccc1)c1ccccc1)=O)C2=O)BrCc1cc(N(c2ccccc2)c(cc2)c(cccc3C([*+]4CCCCBr)=O)c3c2C4=O)ccc1 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 229910052761 rare earth metal Inorganic materials 0.000 description 5
- 238000001291 vacuum drying Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- LUBNKNNXRUCCRO-UHFFFAOYSA-N phenol 1,3,5-trimethylbenzene Chemical compound C1(=CC(=CC(=C1)C)C)C.C1(=CC=CC=C1)O LUBNKNNXRUCCRO-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- DDUHZTYCFQRHIY-UHFFFAOYSA-N 7-chloro-3',4,6-trimethoxy-5'-methylspiro[1-benzofuran-2,4'-cyclohex-2-ene]-1',3-dione Chemical compound COC1=CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 150000002910 rare earth metals Chemical class 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229960001866 silicon dioxide Drugs 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- JDSVRZVMPXFGPE-UHFFFAOYSA-N C1(=CC=CC=C1)C(=O)C1=CC=CC=C1.[F] Chemical compound C1(=CC=CC=C1)C(=O)C1=CC=CC=C1.[F] JDSVRZVMPXFGPE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- ZJHJWUVWYXNFLY-UHFFFAOYSA-N CON(c1ccccc1)c1ccccc1 Chemical compound CON(c1ccccc1)c1ccccc1 ZJHJWUVWYXNFLY-UHFFFAOYSA-N 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-O Oc1cc([OH2+])cc(O)c1 Chemical compound Oc1cc([OH2+])cc(O)c1 QCDYQQDYXPDABM-UHFFFAOYSA-O 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical class C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
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- 238000006482 condensation reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229920005570 flexible polymer Polymers 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
Landscapes
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention relates to a polymer fluorescent material and a preparation method thereof, belonging to the technical field of functional polymer materials. The invention provides the polymer fluorescent material which is prepared by introducing a micro-molecular organic light-emitting group with a definite structure to a side chain of a stable polyarylether non-conjugated polymer and a preparation method thereof; the emission wavelength of the polymer depends on emission of the organic light-emitting group grafted on a main chain of the polymer and is not affected by other groups, the advantages of stability and good processability of the polyarylether polymer enables the application scope of an organic micro-molecular light-emitting material to be greatly expanded, and the prepared polymer fluorescent material can be used in luminescence fields like display, anti-counterfeiting and sensing.
Description
Invention field
The present invention relates to high molecular fluorescent emissive material and its preparation method and application, belong to Functionally structure technical field.
Background of invention
Relative to phosphor, organic light emission micromolecular compound, easily through the meticulous modification of molecular structure, realizes the accuracy controlling of emission wavelength, obtains the glow color and specific emission band expected, can be applied to field more widely.But the easy crystallization of small molecular organic compounds causes molecular aggregates and makes fluorescent emission weaken or cancellation, therefore often need during practical application to adulterate.In addition, when using as anti-fake material, after the volatility of small molecular organic compounds makes the long period, fluorescence occurs disappear and lose distinguishing ability.Thus in Application in Anti-counterfeiting, inorganic materials application is more, but because of its processing difficulties, is difficult to use at specific area.Polymer luminescent material is simple owing to having complete processing, working method is various, with low cost, the outstanding features such as Flexible Displays can be realized and be subject to extensive concern, rare earth compounding luminescence unit is adopted to graft on main polymer chain as Chinese patent 200810012430.X proposes, rare earth luminous realization is utilized to apply widely, but the stability of the coordination incomplete sum rare earth complex compoud unit difference of rare earth ion very easily causes material emission unstable, the more important thing is that its emission wavelength can not regulate owing to relying on the transmitting of rare earth ion, thus lose false proof crypticity.
It is conjugated system aspect that the research contents of polymer luminescent material mainly concentrates at present with backbone structure, there is conjugate unit gathering equally and cause emission wavelength red shift and the defect of the poor stability of material own in it, therefore determine in conjunction with small molecules luminescence unit structure, luminescence band can meticulous adjustment and polymkeric substance easily be processed, the advantage that range of application is wider, select widespread use and the polymeric acceptor of good stability is carrier, grafting small molecules organic light-emitting units, while can stability of material being ensured, utilize the winding of flexible polymer main chain, prevent luminescence unit from assembling cancellation, and determine due to luminescence unit component, obtain the Polymeric fluorescent material of particular transmission wave band.In the present invention, the polyarylether structure of main chain can adopt simple method of condensing to prepare, polymerization is fast, easy purification, second-order transition temperature is high, has satisfactory stability, side chain luminescence unit selects naphthalimide class formation, stablize and easily modify, there is adjustable emission wavelength, realizing all wave band and launch.
Summary of the invention
What the present invention proposed is a kind of main chain is the stabilization of polymer fluorescent emissive materials that non-co-grips polymkeric substance, side chain graft organic molecule unit and fluorescence unit, and its polymer architecture general formula is as follows:
Wherein, n is the polymerization degree, is selected from the positive integer being greater than 10;
Rf is the fluorophor that flexible chain connects, and be the organic group that also can produce fluorescence containing conjugated structure, its structure is as follows:
Wherein, y=0-6; R
1and R
2for substituted radical; R
1be selected from alkyl, alkoxyl group, aryl, N, N-dialkyl amino, N, N-diaryl amido, carboxylic acid or carboxylate groups, sulfonic acid or sulfonate groups, phosphoric acid or phosphate group or quaternary amine group; R
2be selected from alkyl, aryl;
The polymerization degree n of this kind of high molecular fluorescent emissive material is preferably 10-1000;
The group of the fluorophor more preferably following general structural formula that flexible chain connects:
Wherein, y=2,4 or 6; R
1and R
2for substituted radical; R
1preferably from N, N-dialkyl amino, N, N-diaryl amido, carboxylic acid or carboxylate groups, sulfonic acid or sulfonate groups.
The preparation method of this kind of high molecular fluorescent emissive material adopts phenol monomer and corresponding fluorine monomer condensation reaction, and wherein, fluorescent small molecule organic group grafts on phenol structural unit.
Present invention incorporates the advantage of small molecular organic compounds and polymkeric substance, there is strong fluorescent emission, satisfactory stability, can be applicable to all respects of illumination field.
Embodiment
Embodiment 1
The synthesis of polymer P 1:
Synthetic route is as follows:
4-potassium sulfonate-1,8-naphthalene acid anhydride (0.64g, 2.0mmol), 8-bromine octylame (0.42g, after 2.0mmol) mixing with Glacial acetic acid (50mL), stir lower reflux 24 hours, cooling, decompression is lower to desolventizing, obtain oily compound P1-1, not purified, be directly used in next step synthesis.
Compound P1-1 and mesitylene phenol (0.25g, 2.0mmol) be dissolved in DMSO (20mL), drip KOH solution (0.12g is dissolved in 5mL water) under stirring, heat 100 DEG C of reactions 4 hours, the lower remove portion solvent of decompression, add ethanol 60mL to heat, filtered while hot, cooling, obtains compound P1-2, ethyl alcohol recrystallization obtains 0.85g, productive rate: 77%.
Compound P1-2, to fluorine sulfobenzide (0.38g, 1.5mmol), 5mL toluene, 5mL DMF and excessive K
2cO
3be mixed evenly, under stirring, be heated to 160 DEG C of reactions 24 hours.Decompression is lower to desolventizing, a large amount of washing with acetone, dry 0.62g pulverulent solids P1, productive rate: 54%.Number-average molecular weight: 16000; Weight-average molecular weight: 38000; Fluorescent emission peak position: 485nm.
Embodiment 2
The synthesis of polymer P 2:
Synthetic route is as follows:
4-dimethylin-1,8-naphthalene acid anhydride (0.48g, 2.0mmol), 4-bromine butylamine hydrochloride (0.38g, after 2.0mmol) mixing with Glacial acetic acid (50mL), stir lower reflux 24 hours, cooling, in impouring water, be neutralized to PH=7, dichloromethane extraction, dry, decompression is lower to desolventizing, obtain compound P2-1, not purified, be directly used in next step synthesis.
Compound P2-1 and mesitylene phenol (0.25g, 2.0mmol) be dissolved in DMSO (20mL), drip KOH solution (0.12g is dissolved in 5mL water) under stirring, heat 100 DEG C of reactions 4 hours, the lower remove portion solvent of decompression, add dichloromethane extraction, washing, dry, except desolventizing obtains compound P2-2, silicagel column is separated to obtain 0.72g, productive rate: 86%.
Compound P2-2, to fluorine sulfobenzide (0.43g, 1.7mmol), 5mL toluene, 5mL DMF and excessive K
2cO
3be mixed evenly, under stirring, be heated to 160 DEG C of reactions 24 hours.Add methylene dichloride after cooling, be washed to neutrality, dry, be concentrated into about 5ml, sedimentation in methyl alcohol, obtain filamentous polymer P2.Polymkeric substance is after three sedimentations are purified, and vacuum-drying obtains 0.92g, productive rate: 85%.Number-average molecular weight: 94000; Weight-average molecular weight: 196000; Fluorescent emission peak position: 482nm.
Embodiment 3
The synthesis of polymer P 3:
Synthetic route is as follows:
Compound P2-2 (0.75g, 1.8mmol), to fluorine benzophenone (0.39g, 1.8mmol), 5mL toluene, 5mLDMF and excessive K
2cO
3be mixed evenly, under stirring, be heated to 160 DEG C of reactions 24 hours.Add methylene dichloride after cooling, be washed to neutrality, dry, be concentrated into about 5ml, sedimentation in methyl alcohol, obtain filamentous polymer P3.Polymkeric substance is after three sedimentations are purified, and vacuum-drying obtains 0.89g, productive rate: 82%.Number-average molecular weight: 89000; Weight-average molecular weight: 174000; Fluorescent emission peak position: 488nm.
Embodiment 4
The synthesis of polymer P 4:
Synthetic route is as follows:
4-hexichol amido-1,8-naphthalene acid anhydride (0.73g, 2.0mmol), 4-bromine butylamine hydrochloride (0.38g, after 2.0mmol) mixing with Glacial acetic acid (50mL), stir lower reflux 24 hours, cooling, in impouring water, be neutralized to PH=7, dichloromethane extraction, dry, decompression is lower to desolventizing, obtain compound P4-1, not purified, be directly used in next step synthesis.
Compound P4-1 and mesitylene phenol (0.25g, 2.0mmol) be dissolved in DMSO (20mL), drip KOH solution (0.12g is dissolved in 5mL water) under stirring, heat 100 DEG C of reactions 4 hours, the lower remove portion solvent of decompression, add dichloromethane extraction, washing, dry, except desolventizing obtains compound P4-2, silicagel column is separated to obtain 0.86g, productive rate: 78%.
Compound P4-2, to fluorine benzophenone (0.35g, 1.6mmol), 5mL toluene, 5mL DMF and excessive K
2cO
3be mixed evenly, under stirring, be heated to 160 DEG C of reactions 24 hours.Add methylene dichloride after cooling, be washed to neutrality, dry, be concentrated into about 5ml, sedimentation in methyl alcohol, obtain filamentous polymer P4.Polymkeric substance is after three sedimentations are purified, and vacuum-drying obtains 0.84g, productive rate: 73%.Number-average molecular weight: 76000; Weight-average molecular weight: 182000; Fluorescent emission peak position: 518nm.
Embodiment 5
The synthesis of polymer P 5:
Synthetic route is as follows:
Compound P4-2 (0.80g, 1.5mmol), to fluorine sulfobenzide (0.38g, 1.5mmol), 5mL toluene, 5mLDMF and excessive K
2cO
3be mixed evenly, under stirring, be heated to 160 DEG C of reactions 24 hours.Add methylene dichloride after cooling, be washed to neutrality, dry, be concentrated into about 5ml, sedimentation in methyl alcohol, obtain filamentous polymer P5.Polymkeric substance is after three sedimentations are purified, and vacuum-drying obtains 0.89g, productive rate: 78%.Number-average molecular weight: 91000; Weight-average molecular weight: 187000; Fluorescent emission peak position: 514nm.
Embodiment 6
The synthesis of polymer P 6:
Synthetic route is as follows:
3,4,9,10-perylene tetracarboxylic acid dianhydride (0.79g, 2.0mmol), after butylamine (0.2mL, 2.0mmol) and Glacial acetic acid (50mL) mix, stir lower reflux 48 hours, cooling, adds 4-bromine butylamine hydrochloride (0.39g, 2.0mmol), continue backflow 48 hours, cooling, in impouring water, dichloromethane extraction, washing, dry, after filtering and concentrating, silicagel column is separated, and obtains compound P6-2 (1.00g, 86%).
Compound P6-2 (1.00g, 1.7mmol) be dissolved in DMSO (20mL) with mesitylene phenol (0.22g, 1.7mmol), stir lower dropping K0H solution (0.09g is dissolved in 5mL water), heat 100 DEG C of reactions 3 hours, the lower remove portion solvent of decompression, adds dichloromethane extraction, washing, dry, except desolventizing obtains compound P6-3, methylene dichloride/sherwood oil recrystallization obtains 0.88g, productive rate: 83%.
Compound P6-3 (0.88g, 1.4mmol), to fluorine sulfobenzide (0.36g, 1.4mmol), 5mL toluene, 5mL DMF and excessive K
2cO
3be mixed evenly, under stirring, be heated to 160 DEG C of reactions 24 hours.Add chloroform after cooling, be washed to neutrality, dry, be concentrated into about 5ml, sedimentation in methyl alcohol, obtain filamentous polymer P6.Polymkeric substance is after three sedimentations are purified, and vacuum-drying obtains 0.89g, productive rate: 75%.Number-average molecular weight: 67000; Weight-average molecular weight: 158000; Fluorescent emission peak position: 552nm.
Claims (2)
1. the purposes of high molecular fluorescent emissive material in anti-counterfeiting technology, is characterized in that, this polymkeric substance has following general structure:
Wherein, n is the polymerization degree, is selected from the positive integer being greater than 10;
Rf is the fluorophor that flexible chain connects, and it is characterized in that, the fluorophor that wherein said flexible chain connects is selected from the group with following general structural formula:
Wherein, y=2,4 or 6; R
1and R
2for substituted radical; R
1be selected from N, N-dialkyl amino, N, N-diaryl amido, carboxylic acid or carboxylate groups, sulfonic acid or sulfonate groups; R
2be selected from C
4h
9.
2. purposes as claimed in claim 1, is characterized in that the polymerization degree n of described high molecular fluorescent emissive material is 10 < n≤1000.
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| CN105802609B (en) * | 2016-03-28 | 2018-08-24 | 华中科技大学 | A kind of photoresponse room temperature phosphorimetry supermolecule anti-fake material and preparation method thereof |
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| CN102391496B (en) * | 2011-08-31 | 2012-11-07 | 上海大学 | Polyarylether light-emitting material with main chain containing naphthalimide and synthesis method thereof |
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