CN106588975B - A kind of temperature sensitive fluorescent material based on aggregation-induced emission and its preparation method and application - Google Patents
A kind of temperature sensitive fluorescent material based on aggregation-induced emission and its preparation method and application Download PDFInfo
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- CN106588975B CN106588975B CN201611112262.2A CN201611112262A CN106588975B CN 106588975 B CN106588975 B CN 106588975B CN 201611112262 A CN201611112262 A CN 201611112262A CN 106588975 B CN106588975 B CN 106588975B
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- 239000000463 material Substances 0.000 title claims abstract description 43
- 230000002776 aggregation Effects 0.000 title claims abstract description 16
- 238000004220 aggregation Methods 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- TYAQXZHDAGZOEO-KXQOOQHDSA-N 1-myristoyl-2-stearoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)COC(=O)CCCCCCCCCCCCC TYAQXZHDAGZOEO-KXQOOQHDSA-N 0.000 claims abstract description 9
- 208000014446 corneal intraepithelial dyskeratosis-palmoplantar hyperkeratosis-laryngeal dyskeratosis syndrome Diseases 0.000 claims abstract description 9
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 claims abstract description 9
- KILNVBDSWZSGLL-KXQOOQHDSA-N 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC KILNVBDSWZSGLL-KXQOOQHDSA-N 0.000 claims abstract description 6
- NRJAVPSFFCBXDT-HUESYALOSA-N 1,2-distearoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC NRJAVPSFFCBXDT-HUESYALOSA-N 0.000 claims abstract description 6
- IHNKQIMGVNPMTC-UHFFFAOYSA-N (2-hydroxy-3-octadecanoyloxypropyl) 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COP([O-])(=O)OCC[N+](C)(C)C IHNKQIMGVNPMTC-UHFFFAOYSA-N 0.000 claims abstract description 4
- 150000008105 phosphatidylcholines Chemical class 0.000 claims abstract description 3
- 239000000243 solution Substances 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical group CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 8
- 229940125904 compound 1 Drugs 0.000 claims description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 229940125782 compound 2 Drugs 0.000 claims description 5
- 239000008367 deionised water Substances 0.000 claims description 5
- 229910021641 deionized water Inorganic materials 0.000 claims description 5
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical group C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 150000007530 organic bases Chemical class 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 238000004440 column chromatography Methods 0.000 claims description 3
- 239000012043 crude product Substances 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 3
- 235000011152 sodium sulphate Nutrition 0.000 claims description 3
- 235000017060 Arachis glabrata Nutrition 0.000 claims description 2
- 241001553178 Arachis glabrata Species 0.000 claims description 2
- 235000010777 Arachis hypogaea Nutrition 0.000 claims description 2
- 235000018262 Arachis monticola Nutrition 0.000 claims description 2
- 230000006837 decompression Effects 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- 235000020232 peanut Nutrition 0.000 claims description 2
- 239000012266 salt solution Substances 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims 1
- 239000002994 raw material Substances 0.000 abstract description 6
- 239000003814 drug Substances 0.000 abstract description 5
- 238000000034 method Methods 0.000 abstract description 4
- 239000002086 nanomaterial Substances 0.000 abstract description 3
- 239000002105 nanoparticle Substances 0.000 abstract description 3
- -1 tetraphenyl ethylene oxyacetic acid Chemical class 0.000 abstract description 3
- 230000036571 hydration Effects 0.000 abstract description 2
- 238000006703 hydration reaction Methods 0.000 abstract description 2
- LVNGJLRDBYCPGB-LDLOPFEMSA-N (R)-1,2-distearoylphosphatidylethanolamine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[NH3+])OC(=O)CCCCCCCCCCCCCCCCC LVNGJLRDBYCPGB-LDLOPFEMSA-N 0.000 abstract 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 abstract 2
- LZLVZIFMYXDKCN-QJWFYWCHSA-N 1,2-di-O-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC LZLVZIFMYXDKCN-QJWFYWCHSA-N 0.000 abstract 1
- 230000005284 excitation Effects 0.000 description 7
- HEDRZPFGACZZDS-MICDWDOJSA-N deuterated chloroform Substances [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000002861 polymer material Substances 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- JLZUZNKTTIRERF-UHFFFAOYSA-N tetraphenylethylene Chemical group C1=CC=CC=C1C(C=1C=CC=CC=1)=C(C=1C=CC=CC=1)C1=CC=CC=C1 JLZUZNKTTIRERF-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
The present invention discloses a kind of temperature sensitive fluorescent material based on aggregation-induced emission and its preparation method and application.The fluorescent material structure shown in formula I, using tetraphenyl ethylene oxyacetic acid as raw material, through being condensed with stearoyl lysolecithin MSPC.The fluorescent material of the present invention is compounded to form temperature sensitive nano-luminescent material with other phosphatidyl cholines (such as DPPC, DSPC, DAPC) and DSPE PEG2000.By percentage to the quality, raw material composition is：Fluorescent material I 5~30%, phosphatidyl choline 60~90%, DSPE PEG2000 1~10%.Nano-particle is ultrasonically formed using film hydration method, grain size is in 50~85nm.The temperature sensitive fluorescent nano material of the present invention has good temperature response performance, has potential application value in field of medicine release.
Description
Technical field
The present invention relates to field of nano material preparation, and in particular to a kind of temperature sensitive fluorescent material based on aggregation-induced emission
And its preparation method and application.
Background technology
Since at the end of the 20th century, as the subject crossing between medicine, chemistry, biology and materialogy is increasingly close, promote
Into the formation of biological medical polymer material.Intelligent biological medicine material has been used as a kind of biological medical polymer material
As one of current research hotspot.Thermosensitive polymer material is that a kind of responded by thermal stimulus causes phase-state change, so as to
Cause the material of material change in fluorescence itself.
Since it is under aggregation or solid state, four rotating freely for phenyl ring are suppressed tetraphenyl ethylene compound
And fluorescence is sent, it is a kind of typical aggregation-induced emission compound.Due to this special luminescent properties, four benzene second in recent years
Ene derivative is widely used to numerous research fields such as chemical sensor, biosensor and luminous organic material.It is also literary
The delivering of antitumor drug can be used for as biological medicine nano material by offering report tetraphenyl ethylene derivative, and can be monitored
The releasing position of drug and effect.
The content of the invention
It is an object of the invention to provide a kind of temperature sensitive fluorescent material based on aggregation-induced emission and preparation method thereof and
Using.
The technical scheme is that：
A kind of temperature sensitive fluorescent material based on aggregation-induced emission has the structure shown in formula (I)：
The preparation method of the above-mentioned temperature sensitive fluorescent material based on aggregation-induced emission, includes the following steps：
(1) tetraphenyl ethylene oxyacetic acid (compound 1) and stearoyl lysolecithin MSPC (compound 2) are dissolved in solvent
In, the ratio between amount of substance of the compound 1 and MSPC (compound 2) is 1~3:1, and condensing agent and organic base are added in, it stirs
24~48 it is small when；
(2) saturated salt solution is added in after completion of the reaction, is then extracted with ethyl acetate, anhydrous sodium sulfate drying 1~2
Hour, solid sodium sulfate, solution decompression revolving are filtered to remove, crude product column chromatography obtains milky oily compound I, i.e. formula
(I) the temperature sensitive fluorescent material shown in.
Above each compound is with sequence number is distinguish between below each compound in reaction equation.
Further, the ratio between compound 1 and the amount of substance of MSPC are preferably 2:1.
Further, in step (1), the preferred anhydrous methylene chloride of the solvent.
Further, in step (1), the preferred 4-dimethylaminopyridine of the organic base (DMAP).
Further, in step (1), the preferred dicyclohexylcarbodiimide of the condensing agent (DCC).
Above-mentioned fluorescent material is applied to the method for temperature sensitive fluorescent material, includes the following steps：
1) prepare and be dispersed with fluorescent chemicals I, phosphatidyl choline, distearoylphosphatidylethanolamine-polyethylene glycol 2000
(DSPE-PEG2000) chloroformic solution；
2) film is made in mixed raw material sample solution；
3) nano-particle is made in water bath sonicator；
4) wavelength of fluorescence variation with temperature situation is studied.
Specific application process is as follows：
1) fluorescent chemicals I, phosphatidyl choline, the chloroformic solution of DSPE-PEG2000 are prepared respectively, and the concentration of three is 1
~1.5mg/mL；
2) chloroformic solution of fluorescent chemicals I, phosphatidyl choline, DSPE-PEG2000 is taken to be formed in round-bottomed flask respectively to mix
Close solution, vacuum rotary steam 30~45 minutes；
3) deionized water, 30~45min of water bath sonicator, when placement 12~36 is small are added in round-bottomed flask；
4) step 3) acquired solution is taken to dilute 8~15 times, under 325nm excitations, observation fluorescence intensity is with temperature
Raised situation of change.
Further, in the mixed solution of step 2), fluorescent material I, phosphatidyl choline, the quality percentage of DSPE-PEG2000
Than being respectively 5~30%, 60~90% and 1~10%.
Further, the phosphatidyl choline is dipalmitoylphosphatidylcholine (DPPC), Distearoyl Phosphatidylcholine
(DSPC), more than one or both of two peanut phosphatidyl cholines (DAPC).
The beneficial effects of the present invention are：
(1) present invention is ultrasonically formed nano-particle using film hydration method, and grain size is in 50-85nm, resulting materials category
Aggregation-induced emission section bar material, concentration is bigger, and fluorescence is stronger, can greatly improve its application range and application environment.
(3) temperature sensitive fluorescent material provided by the invention is good to temperature-responsive, is raised with temperature, fluorescence intensity gradually becomes
It is weak.
Description of the drawings
Fig. 1 is the scanning electron microscope (SEM) photograph of nano-luminescent material water dispersion solution prepared by the embodiment of the present invention 1.
Fig. 2 is the embodiment of the present invention 1, under 325nm excitations, the fluorescence at 38,40,42,44,46,48,50 DEG C
Intensity, top-down curve (be subject to peak) the corresponding temperature gradually risen respectively.
Fig. 3 is the embodiment of the present invention 2, under 325nm excitations, the fluorescence at 38,40,42,44,46,48,50 DEG C
Intensity, top-down curve (be subject to peak) the corresponding temperature gradually risen respectively.
Fig. 4 is the embodiment of the present invention 2, under 325nm excitations, the fluorescence at 38,40,42,44,46,48,50 DEG C
Intensity, top-down curve (be subject to peak) the corresponding temperature gradually risen respectively.
Wherein, for Fig. 2 into Fig. 4, abscissa represents wavelength (wavelength), and ordinate represents intensity (intensity).
Specific embodiment
The present invention is done below by way of specific embodiment and is further described in detail, but this should not be interpreted as in the present invention
The scope for stating theme is only limitted to following embodiment.All technologies realized based on the above of the present invention belong to the present invention's
Scope.
Instrument and reagent of the present invention：
Nuclear Magnetic Resonance：Bruker AV-II 500MHz NMR, TMS are internal standard, CDCl3For solvent.
Agents useful for same is that commercially available chemistry is pure or analysis is pure.
Embodiment 1
The synthesis of fluorescent chemicals of the present invention
The preparation approach of fluorescent material of the present invention is as follows：
Compound 1 and stearoyl lysolecithin MSPC (compound 2) are dissolved in solvent, the compound 1 and MSPC
The ratio between the amount of substance of (compound 2) is 2:1, and add in DCC and DMAP, be stirred at room temperature 48 it is small when, add in after completion of the reaction full
And saline solution, it is then extracted with ethyl acetate, when anhydrous sodium sulfate drying 2 is small, is filtered to remove solid sodium sulfate, solution subtracts
Pressure revolving, crude product column chromatography obtain milky oily compound I, i.e. fluorescent material shown in formula (I).
Compound I, milky oily liquids, yield 30%；1H NMR(500MHz,CDCl3)δ7.09-7.04(m,9H),
7.01-6.97 (m, 6H), 6.91-6.90 (m, 2H), 6.59-6.57 (m, 2H), 5.31 (s, 1H), 4.58 (dd, J=1.65Hz,
4H), 4.37-4.34 (m, 1H), 4.12-3.97 (m, 4H), 3.68 (s, 1H), 3.24 (s, 9H), 2.21 (t, J=1.0Hz,
2H), 1.54-1.51 (m, 2H), 1.29-1.23 (m, 28H), 0.88 (t, J=1.0Hz, 3H)13C NMR(125MHz,CDCl3)
δ172.7,167.9,155.2,142.7,139.6,139.1,136.2,131.6,130.3,126.7,126.6,125.4,
125.3,112.8,70.9,64.1,61.6,58.3,33.0,30.9,28.7,28.6,28.3,28.1,23.8,21.7,
13.1.HRMS calcd for C54H75NO9P[M+H]+912.5179,found 912.5183.
Embodiment 2
Preparation and fluorescence intensity using DSPC as the temperature sensitive fluorescent material of primary raw material is to the response curve of temperature
Take the DSPE-PEG2000 of the compound I chloroformic solutions of 0.25mL, the DSPC chloroformic solutions of 2.0mL, 0.125mL
Chloroformic solution is in the round-bottomed flask of 25mL, vacuum rotary steam 30min；Then the deionized water of 2.5mL, water bath sonicator are added in
30min, when standing 24 is small；The nano-solution of 0.2mL is taken to be diluted to 2mL, fluorescence intensity is measured and varies with temperature situation, fluorescence light
Spectrometer records the variation of fluorescence intensity at 475nm respectively.The measure that fluorescence intensity varies with temperature in the present embodiment,
Under 325nm excitations, the relational graph that fluorescence intensity varies with temperature is as shown in Figure 2.
Embodiment 3
Preparation and fluorescence intensity using DAPC as the temperature sensitive fluorescent material of primary raw material is to the response curve of temperature
Take the compound I chloroformic solutions of 0.25mL, the DAPC chloroformic solutions of 1.89mL, the DSPE-PEG2000 of 0.125mL
Chloroformic solution in the round-bottomed flask of 25mL, vacuum rotary steam 30min；Then the deionized water of 2.5mL, water bath sonicator are added in
30min, when standing 24 is small；The nano-solution of 0.2mL is taken to be diluted to 2mL, fluorescence intensity is measured and varies with temperature situation, fluorescence light
Spectrometer records the variation of fluorescence intensity at 475nm respectively.The measure that fluorescence intensity varies with temperature in the present embodiment,
Under 325nm excitations, the relational graph that fluorescence intensity varies with temperature is as shown in Figure 3.
Embodiment 4
Preparation and fluorescence intensity using DPPC as the temperature sensitive fluorescent material of primary raw material is to the response curve of temperature
Take the compound I chloroformic solutions of 0.25mL, the DPPC chloroformic solutions of 2.18mL, the DSPE-PEG2000 of 0.125mL
Chloroformic solution in the round-bottomed flask of 25mL, vacuum rotary steam 30min；Then the deionized water of 2.5mL, water bath sonicator are added in
30min, when standing 24 is small；The nano-solution of 0.2mL is taken to be diluted to 2mL, fluorescence intensity is measured and varies with temperature situation, fluorescence light
Spectrometer records the variation of fluorescence intensity at 475nm respectively.The measure that fluorescence intensity varies with temperature in the present embodiment,
Under 325nm excitations, the relational graph that fluorescence intensity varies with temperature is as shown in Figure 4.
Claims (10)
1. a kind of temperature sensitive fluorescent material based on aggregation-induced emission, which is characterized in that there is formula（I）Shown structure：
（I）.
2. the preparation method of the temperature sensitive fluorescent material described in claim 1 based on aggregation-induced emission, which is characterized in that including
Following steps：
（1）Compound 1 and 2 stearoyl lysolecithin MSPC of compound are dissolved in solvent, the compound 1 and MSPC's
The ratio between amount of substance is 1 ~ 3:1, and condensing agent and organic base are added in, when stirring 24 ~ 48 is small；
（2）Saturated salt solution is added in after completion of the reaction, is then extracted with ethyl acetate, when anhydrous sodium sulfate drying 1 ~ 2 is small,
Solid sodium sulfate, solution decompression revolving are filtered to remove, crude product column chromatography obtains milky oily compound I, i.e. formula（I）It is shown
Temperature sensitive fluorescent material.
3. the preparation method of the temperature sensitive fluorescent material according to claim 2 based on aggregation-induced emission, which is characterized in that
The ratio between compound 1 and the amount of substance of MSPC are 2:1.
4. the preparation method of the temperature sensitive fluorescent material according to claim 2 based on aggregation-induced emission, which is characterized in that
The solvent is anhydrous methylene chloride.
5. the preparation method of the temperature sensitive fluorescent material according to claim 2 based on aggregation-induced emission, which is characterized in that
The condensing agent is dicyclohexylcarbodiimide.
6. the preparation method of the temperature sensitive fluorescent material according to claim 2 based on aggregation-induced emission, which is characterized in that
The organic base is 4-dimethylaminopyridine.
7. application of the fluorescent material described in claim 1 in temperature sensitive response fluorescent material.
8. application of the fluorescent material according to claim 7 in temperature sensitive response fluorescent material, which is characterized in that including such as
Lower step：
Fluorescent chemicals I, phosphatidyl choline, the chloroformic solution of DSPE-PEG2000 are prepared, the concentration of three is 1 ~ 1.5mg/mL,
Three kinds of solution is taken to form mixed solutions respectively again, then 30 ~ 45min of vacuum rotary steam adds in deionized water, water bath sonicator 30 ~
45min, then place 12 ~ 36 it is small when, then measure the wavelength of fluorescence under condition of different temperatures.
9. application of the fluorescent material according to claim 7 in temperature sensitive response fluorescent material, which is characterized in that mixing is molten
In liquid, fluorescent material I, phosphatidyl choline, the mass percent of DSPE-PEG2000 are respectively 5 ~ 30%, 60 ~ 90% and 1 ~ 10%.
10. application of the fluorescent material according to claim 8 or claim 9 in temperature sensitive response fluorescent material, which is characterized in that institute
The phosphatidyl choline stated is dipalmitoylphosphatidylcholine, in Distearoyl Phosphatidylcholine, two peanut phosphatidyl cholines
It is one or more kinds of.
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| CN108042803B (en) * | 2017-12-19 | 2020-06-16 | 国家纳米科学中心 | Liposome dispersion liquid loaded with AIE molecules and preparation method and application thereof |
| CN113105349B (en) * | 2021-03-18 | 2023-04-28 | 上海工程技术大学 | Luminescent compound with aggregation induction and supermolecule polymerization fluorescent nano material and preparation method thereof |
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| "Fluorescent Light-up Probe with Aggregation-Induced Emission Characteristics for Alkaline Phosphatase Sensing and Activity Study";Jing Liang et al.,;《ACS Appl. Mater. Interfaces》;20130819;第5卷(第17期);第8784-8789页 * |
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| 四苯乙烯衍生物在有机电致发光材料中的研究进展;罗海媛等;《化工新型材料》;20161015;第44卷(第10期);第14-16页 * |
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| 多功能聚集诱导发光OLED 材料研究进展;陈斌等;《科学通报》;20161120;第61卷(第32期);第3435-3447页 * |
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| CN106588975A (en) | 2017-04-26 |
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