CN102643488A - Preparation method of high-polymer fluorescent microspheres - Google Patents
Preparation method of high-polymer fluorescent microspheres Download PDFInfo
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- CN102643488A CN102643488A CN2012101065377A CN201210106537A CN102643488A CN 102643488 A CN102643488 A CN 102643488A CN 2012101065377 A CN2012101065377 A CN 2012101065377A CN 201210106537 A CN201210106537 A CN 201210106537A CN 102643488 A CN102643488 A CN 102643488A
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- vinylbenzene
- microballoon
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- 239000004005 microsphere Substances 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- 229920000642 polymer Polymers 0.000 title claims abstract description 15
- 239000002243 precursor Substances 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 10
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims abstract description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 21
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- 229920001467 poly(styrenesulfonates) Polymers 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000011257 shell material Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 230000032696 parturition Effects 0.000 claims description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical compound CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 2
- 229940043232 butyl acetate Drugs 0.000 claims description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 claims description 2
- 229940005991 chloric acid Drugs 0.000 claims description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000006408 oxalic acid Nutrition 0.000 claims description 2
- 238000012545 processing Methods 0.000 claims description 2
- 238000001179 sorption measurement Methods 0.000 claims description 2
- 229920000547 conjugated polymer Polymers 0.000 abstract description 6
- 230000008030 elimination Effects 0.000 abstract description 5
- 238000003379 elimination reaction Methods 0.000 abstract description 5
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- 239000008096 xylene Substances 0.000 abstract description 4
- 239000011540 sensing material Substances 0.000 abstract description 3
- 230000001105 regulatory effect Effects 0.000 abstract description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 abstract 5
- 230000009286 beneficial effect Effects 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 230000001276 controlling effect Effects 0.000 abstract 1
- -1 poly(p-phenylenevinylene) Polymers 0.000 abstract 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical group C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 13
- 239000000178 monomer Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000006228 supernatant Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000000502 dialysis Methods 0.000 description 2
- 238000004134 energy conservation Methods 0.000 description 2
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000007877 drug screening Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 230000003534 oscillatory effect Effects 0.000 description 1
- 238000000734 protein sequencing Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012163 sequencing technique Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
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- Manufacturing Of Micro-Capsules (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
Abstract
The invention discloses a preparation method of high-polymer fluorescent microspheres, particularly a preparation method of microspheres carrying fluorescence-emission poly(p-phenylenevinylene) (PPV) conjugated polymers on the surface, belonging to the field of preparation of fluorescent sensing materials. The preparation method comprises the following steps: preparing a PPV precursor solution by a sulfosalt precursor process, adding microspheres carrying the PPV sulfosalt precursor into a xylene solution, and adding a catalyst to eliminate catalytic thiophane groups in the solution. The invention provides a new way for preparing high-polymer fluorescent microspheres. Since the process different from conventional thermal elimination is adopted, the invention provides possibilities for relatively quantitatively controlling the fluorescence-emission performance of the fluorescent microspheres by regulating the structure of the PPV precursor; and meanwhile, the process of elimination in solution is utilized to prepare the fluorescent microspheres, so the invention has the advantage of lower reaction temperature and is beneficial to energy saving as compared with the prior art.
Description
Technical field
The present invention relates to a kind of area load has fluorescent emission to gather the preparation method to the microballoon of vinylbenzene support type conjugated polymer, belongs to the fluorescent sensing material preparation field.
Background technology
Fluorescent microsphere is a kind of novel fluorescent sensing material; Good prospects for application is arranged, and research shows that it can be used for numerous biologic medical association areas; Like gene sequencing and expression, protein sequencing, medical diagnosis on disease and drug screening; At aspects such as environmental monitoring and food test a large amount of demands is arranged also, simultaneously, also for another cutting edge technology---the development of liquid-phase chip suspension technology provides the foundation.
Chinese invention patent (CN 101824191 A) discloses a kind of high molecular fluorescent microballoons and preparation method thereof; With monodispersed sulfonated polystyrene microsphere is raw material; The precursor polymer of conjugated polymer gathered vinylbenzene support presoma (pre-PPV) is adsorbed on the microballoon through electrostatic attraction; Heat is eliminated under 90～140 ℃ of conditions of vacuum again, makes the fluorescent microsphere of conjugated polymer PPV load.Yet eliminate the backbone structure that process can't the finely regulating conjugated polymer when using this method in heat, as can't be further coming the conjugated degree etc. of quantitative control main chain through some structure of regulation and control presoma.
Document (J.Am. Chem.Soc.2000; 122; 2244-2251) having reported will be with PPV precursor polymer and the methyl alcohol and the carboxylic acid generation substitution reaction of side chain; Be dissolved in the xylene solution then, and add the catalyzer quadrol, thereby make different PPV through heating selectivity elimination in solution.This technology is not also seen the preparation that is used for device preparation or fluorescent microsphere.
Summary of the invention
The purpose of this invention is to provide a kind of stable performance, help the energy-conservation method for preparing fluorescent microsphere.
The technical scheme that the present invention adopts provides a kind of preparation method of high molecular fluorescent microballoons, makes with the salt precursor body method of giving birth and gathers behind the vinylbenzene support precursor solution, carries out the processing of following steps again:
(1) monodispersed, sulfonated polystyrene microsphere are joined gathers, again microballoon is taken out, after washing, drying, obtain surface adsorption and gather the microballoon that vinylbenzene is supportted presoma thorough mixing in the vinylbenzene support precursor solution;
(2) microballoon with step (1) gained joins in the solvent under the anhydrous and oxygen-free condition; Add catalyzer; Be to take out microballoon after vibrating 1～12 hour under 60 ℃～110 ℃ the condition in temperature; Through washing, drying, obtaining a kind of shell material is to gather the fluorescent microsphere that vinylbenzene is supportted fluorescence conjugated high molecular polymer again.
The described molecular structural formula that gathers vinylbenzene support presoma is:
Wherein, n is the number of the effective conjugate unit of polymkeric substance, 10≤n≤50; R
1, R
2Identical or different, R
1, R
2Be H, OCH
2COOH, OCH
2COOCH
3, OC
3H
6SO
3Na, F, Br or C
xH
yA kind of among the O; Described C
xH
yAmong the O, y=2x+1, x is 0～12 integer.
Described shell material gathers vinylbenzene is supportted fluorescence conjugated high molecular polymer, and its structural formula is:
Wherein, n is the number of the effective conjugate unit of polymkeric substance, 10≤n≤50; R
1, R
2Identical or different, R
1, R
2Be H, OCH
2COOH, OCH
2COOCH
3, OC
3H
6SO
3Na, F, Br or C
xH
yA kind of among the O; Described C
xH
yAmong the O, y=2x+1, x is 0～12 integer.
Described solvent is a kind of in octane, butylacetate, chlorobenzene, toluene, o-Xylol, m-xylene, p-Xylol, YLENE, N, dinethylformamide, N, N-N,N-DIMETHYLACETAMIDE, hexalin, 1,2-Ucar 35, the terepthaloyl moietie, or their combination.
Described catalyzer is a kind of in mineral acid hydrogenchloride, hydrogen sulfide, chloric acid, sulfuric acid, sulfurous acid, the phosphoric acid, or their combination.
Described catalyzer is a kind of in organic acid tosic acid, Phenylsulfonic acid, acetate, oxalic acid, oxyacetic acid, Hydrocerol A, the YD 30, or their combination.
Principle of the present invention is: load is had to gather the give birth microballoon of salt precursor body of vinylbenzene support class is eliminated in xylene solution, when the polymer precursor of load support vinylbenzene for gathering, the adding catalyzer can the elimination of catalysis THTP group in solution.
The present invention's advantage compared with prior art is: be different from the method that conventional heat is eliminated owing to adopted; Obtained a kind of fluorescent microsphere, maybe for realizing coming the fluorescent emission performance of relative quantification ground control fluorescent microsphere to provide through the structure of regulation and control PPV presoma; Simultaneously, be employed in the method for eliminating in the solution and prepare fluorescent microsphere, temperature of reaction is low than prior art, helps energy-conservation.
Description of drawings
Fig. 1 is the fluorescence emission spectrogram of the high molecular fluorescent microballoons that provides of the embodiment of the invention;
Fig. 2 is the polymer monomer and the infrared absorption spectrum comparison diagram that gathers the vinylbenzene support of the unprotected side chain that provides of the embodiment of the invention;
Fig. 1 is the SEM figure of prepared microballoon in each step of the embodiment of the invention.
Embodiment
Below in conjunction with accompanying drawing and embodiment technical scheme of the present invention is further elaborated.
Embodiment 1
Present embodiment provides a kind of preparation method of high molecular fluorescent microballoons, and step is following:
1, adopt the salt precursor body legal system of giving birth to be equipped with solution: under anhydrous and oxygen-free (nitrogen protection) condition; Press document (J. Am.Chem. Soc1993; 115,10117-10124) polymer monomer of synthetic unprotected side chain is got this monomer 0.6895 g (1.965mMol) and is dissolved in 12 mL H
2Among the O, then the 1.7 mL NaOH aqueous solution are slowly added wherein, in ice-water bath, stir after 1 hour, adding 3 mL concentration is the HCl solution termination reaction of 2 M; The use molecular weight is 1 day (2 * 500 mL deionized water H of dialysis tubing dialysis of 3500
2O), obtain PPV precursor solution 20 mL, its synthetic route is as follows:
，
10≤n≤50, n is a positive integer.
2, the PPV precursor solution that 3 mL steps 1 is obtained mixes with monodispersed, the sulfonated polystyrene microsphere of 0.3 g diameter, 35 μ m, vibrates after 1 hour, and is centrifugal, removes supernatant; In microballoon, add the vibration of 8 mL deionized waters and washed in 1 hour, centrifugal and remove supernatant; Use the deionized water with volume respectively, press the above-mentioned steps washing once with the absolute ethyl alcohol of volume, finish-drying under the vacuum state obtains gathering the microballoon that vinylbenzene support presoma is coated.
3, the microballoon that step 2 is obtained joins in the 3 mL xylene solutions, adds 0.2 mL tosic acid, is reflected under the anhydrous and oxygen-free condition and carries out; 80 ℃ of following oscillatory reactions 3 hours, after the solution cooling, add 5 mL acetone; Centrifugal; Remove supernatant, in microballoon, add 8 mL acetone vibration 1 hour again, centrifugal and remove supernatant.Use the deionized water with volume more respectively, with the absolute ethanol washing of volume once, finish-drying under the vacuum state obtains monodispersed, sulfonated polystyrene microsphere, and its surface coats to gather supports fluorescence conjugated polymer to vinylbenzene.
Referring to accompanying drawing 1, it is by the fluorescence emission spectrogram of the fluorescent microsphere of present embodiment technical scheme preparation, can be found out that by Fig. 1 under 405 nm exciting lights, the maximum emission wavelength of this fluorescent microsphere is 544 nm.
Referring to accompanying drawing 2, curve a is the infrared absorption spectrum of the polymer monomer of unprotected side chain in the present embodiment, and curve b is the infrared absorption spectrum that gathers in the present embodiment the vinylbenzene support, can be found out 2082 cm by Fig. 2
-1The peak at place is CH in the monomer
2The stretching vibration of the c h bond of Cl, 960cm
-1The peak at place is the flexural vibration that gather the two key C-H of C=C in the vinylbenzene support.
Referring to accompanying drawing 3, figure a is the SEM figure of raw material ball, figure b be precursor polymer be carried on eliminate on the microballoon before, i.e. the figure of the SEM of microballoon described in the present embodiment step 2, figure c is the polymer microballoon after eliminating, the i.e. figure of the SEM of microballoon described in the present embodiment step 3.Can find out: do not have considerable change with elimination back microsphere surface than raw material ball before eliminating.
Claims (6)
1. the preparation method of a high molecular fluorescent microballoons makes with the salt precursor body method of giving birth and to gather vinylbenzene support precursor solution, it is characterized in that carrying out the processing of following steps again:
(1) monodispersed, sulfonated polystyrene microsphere are joined gathers, again microballoon is taken out, after washing, drying, obtain surface adsorption and gather the microballoon that vinylbenzene is supportted presoma thorough mixing in the vinylbenzene support precursor solution;
(2) microballoon with step (1) gained joins in the solvent under the anhydrous and oxygen-free condition; Add catalyzer; Be to take out microballoon after vibrating 1～12 hour under 60 ℃～110 ℃ the condition in temperature; Through washing, drying, obtaining a kind of shell material is to gather the fluorescent microsphere that vinylbenzene is supportted fluorescence conjugated high molecular polymer again.
2. the preparation method of a kind of high molecular fluorescent microballoons according to claim 1 is characterized in that: the described molecular structural formula that gathers vinylbenzene support presoma is:
Wherein, n is the number of the effective conjugate unit of polymkeric substance, 10≤n≤50; R
1, R
2Identical or different, R
1, R
2Be H, OCH
2COOH, OCH
2COOCH
3, OC
3H
6SO
3Na, F, Br or C
xH
yA kind of among the O; Described C
xH
yAmong the O, y=2x+1, x is 0～12 integer.
3. the preparation method of a kind of high molecular fluorescent microballoons according to claim 1 is characterized in that: described shell material gathers vinylbenzene is supportted fluorescence conjugated high molecular polymer, and its structural formula is:
Wherein, n is the number of the effective conjugate unit of polymkeric substance, 10≤n≤50; R
1, R
2Identical or different, R
1, R
2Be H, OCH
2COOH, OCH
2COOCH
3, OC
3H
6SO
3Na, F, Br or C
xH
yA kind of among the O; Described C
xH
yAmong the O, y=2x+1, x is 0～12 integer.
4. the preparation method of a kind of high molecular fluorescent microballoons according to claim 1; It is characterized in that: described solvent is a kind of in octane, butylacetate, chlorobenzene, toluene, o-Xylol, m-xylene, p-Xylol, YLENE, N, dinethylformamide, N, N-N,N-DIMETHYLACETAMIDE, hexalin, 1,2-Ucar 35, the terepthaloyl moietie, or their combination.
5. the preparation method of a kind of high molecular fluorescent microballoons according to claim 1 is characterized in that: described catalyzer is a kind of in mineral acid hydrogenchloride, hydrogen sulfide, chloric acid, sulfuric acid, sulfurous acid, the phosphoric acid, or their combination.
6. the preparation method of a kind of high molecular fluorescent microballoons according to claim 1; It is characterized in that: described catalyzer is a kind of in organic acid tosic acid, Phenylsulfonic acid, acetate, oxalic acid, oxyacetic acid, Hydrocerol A, the YD 30, or their combination.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103788942A (en) * | 2014-02-24 | 2014-05-14 | 苏州大学 | Eu<3+> and rhodamine 6G doped polymer fluorescent encoding microsphere and preparation method |
| CN104209071A (en) * | 2014-08-08 | 2014-12-17 | 四川大学 | Preparation method of high-molecular fluorescent microsphere |
| CN104845052A (en) * | 2015-05-08 | 2015-08-19 | 苏州大学 | Poly phenylenevinylene conjugated polymer fluorescent nanoparticles with controllable emission wavelength and preparation method |
| CN105924628A (en) * | 2016-06-20 | 2016-09-07 | 苏州大学 | Poly(p-phenylene vinylene) precursor, preparation method thereof and application of poly(p-phenylene vinylene) precursor to high-molecular fluorescent microspheres |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101824191A (en) * | 2010-04-29 | 2010-09-08 | 苏州大学 | Macromolecular fluorescent microspheres and preparation method thereof |
-
2012
- 2012-04-12 CN CN201210106537.7A patent/CN102643488B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101824191A (en) * | 2010-04-29 | 2010-09-08 | 苏州大学 | Macromolecular fluorescent microspheres and preparation method thereof |
Non-Patent Citations (2)
| Title |
|---|
| 《Journal of the American Chemical Society》 20000223 G. Padmanaban et al. "Conjugation Length Control in Soluble Poly[2-methoxy -5- ((2'-ethylhexyl)oxy) -1,4-phenylenevinylene] (MEHPPV): Synthesis, Optical Properties, and Energy Transfer" 2244-2251 1-6 第122卷, 第10期 * |
| G. PADMANABAN ET AL.: ""Conjugation Length Control in Soluble Poly[2-methoxy -5- ((2’-ethylhexyl)oxy) -1,4-phenylenevinylene] (MEHPPV): Synthesis, Optical Properties, and Energy Transfer"", 《JOURNAL OF THE AMERICAN CHEMICAL SOCIETY》 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103788942A (en) * | 2014-02-24 | 2014-05-14 | 苏州大学 | Eu<3+> and rhodamine 6G doped polymer fluorescent encoding microsphere and preparation method |
| CN103788942B (en) * | 2014-02-24 | 2015-09-23 | 苏州大学 | Doping Eu 3+with high molecular fluorescent coding microball and the preparation method of rhodamine 6G |
| CN104209071A (en) * | 2014-08-08 | 2014-12-17 | 四川大学 | Preparation method of high-molecular fluorescent microsphere |
| CN104845052A (en) * | 2015-05-08 | 2015-08-19 | 苏州大学 | Poly phenylenevinylene conjugated polymer fluorescent nanoparticles with controllable emission wavelength and preparation method |
| CN104845052B (en) * | 2015-05-08 | 2017-03-22 | 苏州大学 | Poly phenylenevinylene conjugated polymer fluorescent nanoparticles with controllable emission wavelength and preparation method |
| CN105924628A (en) * | 2016-06-20 | 2016-09-07 | 苏州大学 | Poly(p-phenylene vinylene) precursor, preparation method thereof and application of poly(p-phenylene vinylene) precursor to high-molecular fluorescent microspheres |
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|---|---|
| CN102643488B (en) | 2014-05-14 |
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