CN106634969B - A kind of fluorescent chemicals and its preparation method and application based on tetraphenyl ethylene - Google Patents
A kind of fluorescent chemicals and its preparation method and application based on tetraphenyl ethylene Download PDFInfo
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- CN106634969B CN106634969B CN201611269867.2A CN201611269867A CN106634969B CN 106634969 B CN106634969 B CN 106634969B CN 201611269867 A CN201611269867 A CN 201611269867A CN 106634969 B CN106634969 B CN 106634969B
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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
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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Abstract
The present invention discloses a kind of fluorescent chemicals and its preparation method and application based on tetraphenyl ethylene.Shown in the fluorescent chemicals structure such as formula (I), using tetraphenyl ethylene glycolic acid as raw material, through being condensed with glycerin monostearate, open loop then is reacted with succinic anhydride again and is formed.Fluorescent chemicals and other phosphatidyl cholines (such as DPPC, DSPC, DAPC) of the invention and DSPE-PEG2000 are compounded to form temperature sensitive nano-luminescent material.By percentage to the quality, raw material forms are as follows: fluorescent chemicals I 5~30%, phosphatidyl choline 60~90%, DSPE-PEG2000 1~10%.The present invention is ultrasonically formed nanoparticle, partial size average-size 50nm or so using film hydration method, and the temperature sensitive fluorescent nano material of gained has good temperature response performance, has potential application 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 fluorescent chemicals based on tetraphenyl ethylene and
Preparation method and application.
Background technique
The most of fluorescence quantum yield with higher in weak solution of traditional fluorescent chemicals, and in high concentration or
Fluorescent weakening even quenches under coherent condition, and this aggregation inducing quenching effect greatly limits their application range.Aggregation
Induced luminescence phenomenon is to be reported by Tang this loyalty academician in 2001, causes the extensive concern of scientific circles.Five phenyl sila rings
The compounds such as pentadiene, tetraphenyl ethylene, bigcatkin willow azine, triarylamine are found to have good aggregation inducing effect.
Tetraphenyl ethylene compound is a kind of typical aggregation-induced emission compound, under aggregation or solid state,
Four rotating freely for phenyl ring are suppressed and issue fluorescence.Due to this special luminescent properties, tetraphenyl ethylene spreads out in recent years
Biology is widely used to numerous research fields such as chemical sensor, biosensor and luminous organic material.There are also texts simultaneously
Offering report, it can be used for the transport of anti-tumor drug as biological medicine nano material, and can monitor the release position of drug
It sets and effect.
Summary of the invention
The purpose of the present invention is to provide a kind of fluorescent chemicals and its preparation method and application based on tetraphenyl ethylene.
The technical solution of the present invention is as follows:
A kind of fluorescent chemicals based on tetraphenyl ethylene have structure shown in formula (I):
The preparation method of the above-mentioned fluorescent chemicals based on tetraphenyl ethylene, includes the following steps:
(1) tetraphenyl ethylene glycolic acid, that is, compound 1 is dissolved in methylene chloride, adds thionyl chloride, thionyl chloride with
The ratio between amount of substance of compound 1 is 1~5:1, and n,N-Dimethylformamide is added dropwise, and is heated to reflux 3~8 hours, so
Vacuum rotary steam removes volatile solvent and obtains acid chloride intermediate afterwards, adds anhydrous methylene chloride and obtains mixed solution；It will mixing
Solution is added drop-wise to containing in the glycerin monostearate i.e. dichloromethane solution of compound 2 and organic base, compound 1, compound 2
It is 1~2:1:1~3 with the ratio between the amount of substance of organic base three, is stirred at room temperature 24~48 hours, saturation is added after completion of the reaction
Then saline solution is extracted with ethyl acetate, 1~2 hour dry with anhydrous sodium sulfate, is filtered to remove solid sodium sulfate, molten
Liquid vacuum rotary steam, crude product column chromatograph to obtain milky oily compound i.e. compound 3；Shown in its reaction equation such as formula (II):
(2) compound 3 and succinic anhydride, that is, compound 4 are dissolved in solvent, the amount of the substance of compound 4 and compound 3
The ratio between be 1~10:1, and organic base is added, is stirred at room temperature 24~48 hours, saturated salt solution is added after completion of the reaction, then uses
Ethyl acetate is extracted, and with anhydrous sodium sulfate dry 1~2 hour, is filtered to remove solid sodium sulfate, solution vacuum rotary steam, slightly
Product column chromatographs to obtain milky oily compound, i.e. fluorescent chemicals (fluorescent chemicals I) shown in formula (I)；Its reaction equation
As shown in formula (III):
Above each compound is distinguish with serial number below compound each in reaction equation.
Further, the ratio between amount of substance of compound 2 and compound 1 is preferably 2:1.
Further, in step (1), the preferred triethylamine of the organic base.
Further, in step (2), the preferred anhydrous methylene chloride of the solvent.
Further, in step (2), the preferred 4-dimethylaminopyridine of the organic base (DMAP).
Above-mentioned fluorescent chemicals are applied to the method for temperature sensitive fluorescent material, include the following steps:
1) chloroformic solution for being dispersed with fluorescent chemicals I, phosphatidyl choline, DSPE-PEG2000 is prepared；
2) film is made in mixed raw material sample solution；
3) nanoparticle is made in water bath sonicator；
4) wavelength of fluorescence variation with temperature situation is studied.
Specific application method is as follows:
1) chloroformic solution of fluorescent chemicals I, phosphatidyl choline, DSPE-PEG2000 are prepared respectively, and the concentration of three is 1
~1.5mg/mL；
2) take respectively fluorescent chemicals I, phosphatidyl choline, DSPE-PEG2000 chloroformic solution formed in a round bottom flask it is mixed
Conjunction solution, vacuum rotary steam 30~45 minutes；
3) deionized water is added in round-bottomed flask, 30~45min of water bath sonicator is placed 12~36 hours；
4) it takes step 3) acquired solution to dilute 8~15 times, under 325nm excitation, observes fluorescence intensity with temperature
Raised situation of change.
Further, in the mixed solution of step 2), the quality hundred of fluorescent chemicals I, phosphatidyl choline, DSPE-PEG2000
Divide than being respectively 5~30%, 60~90% and 1~10%.
Further, the phosphatidyl choline is dipalmitoylphosphatidylcholine (DPPC), Distearoyl Phosphatidylcholine
(DSPC), one or more of two peanut phosphatidyl cholines (DAPC).
The beneficial effects of the present invention are:
(1) present invention is ultrasonically formed nanoparticle using film hydration method, and partial size average-size is in 50nm or so, gained material
Material belongs to aggregation-induced emission profile material, and concentration is bigger, and fluorescence is stronger, can greatly improve its application range and application environment.
(2) temperature sensitive fluorescent material provided by the invention is good to temperature-responsive, increases with temperature, fluorescence intensity gradually becomes
It is weak.
Detailed description of the invention
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 excitation, at 25,38,40,42,44,46,48,50 DEG C
Fluorescence intensity, top-down curve (be subject to highest point) respectively correspond the temperature gradually risen.
Fig. 3 is the embodiment of the present invention 2, under 325nm excitation, the fluorescence at 38,40,42,44,46,48,50 DEG C
Intensity, top-down curve (be subject to highest point) respectively correspond the temperature gradually risen.
Fig. 4 is the embodiment of the present invention 2, under 325nm excitation, the fluorescence at 38,40,42,44,46,48,50 DEG C
Intensity, top-down curve (be subject to highest point) respectively correspond the temperature gradually risen.
Wherein, for Fig. 2 into Fig. 4, abscissa indicates wavelength (wavelength), and ordinate indicates 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 range for stating theme is only limitted to embodiment below.All technologies realized based on above content of the present invention belong to of the invention
Range.
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:
2mmol compound 1 is dissolved in 10mL methylene chloride, thionyl chloride, the substance of thionyl chloride and compound 1 is added
The ratio between amount be 5:1, and a drop n,N-Dimethylformamide is added, is heated to reflux 4 hours, then vacuum rotary steam removes volatility
Solvent obtains acid chloride intermediate, adds anhydrous methylene chloride and obtains mixed solution.Mixed solution is slowly added drop-wise to containing
In the 5mL dichloromethane solution of 1mmol glycerin monostearate and 2mmol triethylamine, it is stirred at room temperature 48 hours, after completion of the reaction
Saturated salt solution is added, is then extracted with ethyl acetate, it is 2 hours dry with anhydrous sodium sulfate, then it is filtered to remove sulfuric acid
Sodium solid, solution vacuum rotary steam, crude product column chromatograph to obtain milky oily compound 3.
2-hydroxy-3-(2-(4-(1,2,2-triphenylvinyl)phenoxy)acetoxy)propyl
stearate(3),liquid.1H NMR(500MHz,CDCl3)δ7.11-7.06(m,9H),7.03-6.98(m,6H),6.95-
6.93(m,2H),6.65-6.63(m,2H),4.61(s,2H),4.36-4.05(m,4H),2.36-2.29(m,2H),1.68-
1.56 (m, 3H), 1.33-1.19 (m, 28H), 0.88 (t, J=1.0Hz, 3H)13C NMR(125MHz,CDCl3)δ173.9,
168.9,156.1,143.8,140.5,140.2,137.4,132.6,131.3,127.8,127.6,126.4,126.3,
113.8,68.1,65.8,65.2,64.8,34.1,31.9,29.7,29.6,29.2,29.1,24.9,22.7,14.1.HRMS
calcd for C49H63O6[M+H]+747.4625,found 747.4628.
Compound 3 and succinic anhydride are dissolved in methylene chloride, the ratio between the succinic anhydride and the amount of substance of compound 3
For 10:1, and 4-dimethylaminopyridine is added, is stirred at room temperature 24 hours, saturated salt solution is added after completion of the reaction, then uses second
Acetoacetic ester is extracted, 1 hour dry with anhydrous sodium sulfate, is then filtered to remove solid sodium sulfate, and solution vacuum rotary steam is thick to produce
Object column chromatographs to obtain milky oily compound, i.e. fluorescent chemicals (fluorescent chemicals I) shown in formula (I).
4-oxo-4-(1-(stearoyloxy)-3-(2-(4-(1,2,2-triphenylvinyl)phenoxy)
acetoxy)propan-2-yloxy)butanoic acid(I),liquid.1H NMR(500MHz,CDCl3)δ7.11-7.06
(m,9H),7.03-6.99(m,6H),6.95-6.93(m,2H),6.65-6.62(m,2H),5.38-5.25(m,1H),4.56
(s,1H),4.38-4.11(m,4H),2.65-2.60(m,4H),2.32-2.29(m,2H),1.68-1.56(m,2H),1.33-
1.19 (m, 28H), 0.88 (t, J=1.0Hz, 3H)13C NMR(125MHz,CDCl3)δ177.1,173.2,171.3,168.6,
156.1,143.8,140.5,140.2,137.4,132.6,131.3,128.2,127.6,126.4,126.3,113.8,69.7,
65.0,62.7,61.8,60.6,34.1,31.9,29.8,29.2,28.7,25.0,22.5,21.0,20.6,14.3.HRMS
calcd for C53H67O9[M+H]+847.4785,found847.4781.
Embodiment 2
It is the preparation of the temperature sensitive fluorescent material of primary raw material and fluorescence intensity to the response curve of temperature using DSPC
Take the DSPE- of the fluorescent chemicals I chloroformic solution of 0.23mL, the DSPC chloroformic solution of 2.0mL, 0.125mL
The chloroformic solution of PEG2000 is in the round-bottomed flask of 25mL, vacuum rotary steam 30min；Then the deionized water of 2.5mL, water is added
Ultrasound 30min is bathed, stands 24 hours；The nano-solution of 0.2mL is taken to be diluted to 2mL, measurement fluorescence intensity varies with temperature situation,
Fluorescence Spectrometer records the variation of fluorescence intensity at 475nm respectively.The measurement that fluorescence intensity varies with temperature in the present embodiment,
Under 325nm excitation, the relational graph that fluorescence intensity varies with temperature is as shown in Figure 2.
Embodiment 3
It is the preparation of the temperature sensitive fluorescent material of primary raw material and fluorescence intensity to the response curve of temperature using DAPC
Take the DSPE-PEG2000 of the compound I chloroformic solution of 0.23mL, the DAPC chloroformic solution of 1.89mL, 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 is added
30min stands 24 hours；The nano-solution of 0.2mL is taken to be diluted to 2mL, measurement fluorescence intensity varies with temperature situation, fluorescence light
Spectrometer records the variation of fluorescence intensity at 475nm respectively.The measurement that fluorescence intensity varies with temperature in the present embodiment,
Under 325nm excitation, the relational graph that fluorescence intensity varies with temperature is as shown in Figure 3.
Embodiment 4
It is the preparation of the temperature sensitive fluorescent material of primary raw material and fluorescence intensity to the response curve of temperature using DPPC
Take the DSPE-PEG2000 of the compound I chloroformic solution of 0.23mL, the DPPC chloroformic solution of 2.18mL, 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 is added
30min stands 24 hours；The nano-solution of 0.2mL is taken to be diluted to 2mL, measurement fluorescence intensity varies with temperature situation, fluorescence light
Spectrometer records the variation of fluorescence intensity at 475nm respectively.The measurement that fluorescence intensity varies with temperature in the present embodiment,
Under 325nm excitation, the relational graph that fluorescence intensity varies with temperature is as shown in Figure 4.
Claims (7)
1. a kind of fluorescent chemicals based on tetraphenyl ethylene, which is characterized in that have structure shown in formula (I):
2. the preparation method of the fluorescent chemicals described in claim 1 based on tetraphenyl ethylene, which is characterized in that including walking as follows
It is rapid:
(1) tetraphenyl ethylene glycolic acid, that is, compound 1 is dissolved in methylene chloride, thionyl chloride, thionyl chloride and compound 1 is added
The ratio between the amount of substance be 1~5:1, and n,N-Dimethylformamide is added dropwise, is heated to reflux 3~8 hours, then decompression rotation
Volatile solvent is evaporated off and obtains acid chloride intermediate, adds anhydrous methylene chloride and obtains mixed solution；Slowly by mixed solution
It is added drop-wise to containing in the glycerin monostearate i.e. dichloromethane solution of compound 2 and triethylamine, compound 1, compound 2 and has
The ratio between amount of substance of machine alkali three is 1~2:1:1~3, is stirred at room temperature 24~48 hours, saturated common salt is added after completion of the reaction
Then water is extracted with ethyl acetate, 1~2 hour dry with anhydrous sodium sulfate, is filtered to remove solid sodium sulfate, solution subtracts
Pressure revolving, crude product column chromatograph to obtain milky oily compound i.e. compound 3；Shown in its reaction equation such as formula (II):
(2) compound 3 and succinic anhydride, that is, compound 4 are dissolved in solvent, the ratio between compound 4 and the amount of substance of compound 3
For 1~10:1, and organic base is added, is stirred at room temperature 24~48 hours, saturated salt solution is added after completion of the reaction, then uses acetic acid
Ethyl ester is extracted, 1~2 hour dry with anhydrous sodium sulfate, is filtered to remove solid sodium sulfate, solution vacuum rotary steam, crude product
Column chromatographs to obtain milky oily compound, as fluorescent chemicals I；Shown in its reaction equation such as formula (III):
3. the preparation method of the fluorescent chemicals according to claim 2 based on tetraphenyl ethylene, which is characterized in that step
(1) the ratio between amount of substance of compound 2 and compound 1 is 2:1 in.
4. the preparation method of the fluorescent chemicals according to claim 2 based on tetraphenyl ethylene, which is characterized in that step
(2) organic solvent described in is methylene chloride.
5. the preparation method of the fluorescent chemicals according to claim 2 based on tetraphenyl ethylene, which is characterized in that step
(2) organic base described in is 4-dimethylaminopyridine.
6. application of the fluorescent chemicals described in claim 1 in temperature sensitive response fluorescent material, which is characterized in that including as follows
Step:
The chloroformic solution of fluorescent chemicals I, phosphatidyl choline, DSPE-PEG2000 are prepared, the concentration of three is 1~1.5mg/
ML, then three kinds of solution is taken to form mixed solution respectively, then deionized water, water bath sonicator 30 is added in 30~45min of vacuum rotary steam
~45min, then place 12~36 hours, then measure the wavelength of fluorescence under condition of different temperatures；The phosphatidyl choline is
One or more of dipalmitoylphosphatidylcholine, Distearoyl Phosphatidylcholine, two peanut phosphatidyl cholines.
7. application of the fluorescent chemicals according to claim 6 in temperature sensitive response fluorescent material, which is characterized in that mixing
In solution, fluorescent material I, phosphatidyl choline, DSPE-PEG2000 mass percent be respectively 5~30%, 60~90% and 1~
10%.
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| CN111826153B (en) * | 2020-06-08 | 2022-11-22 | 上海大学 | Temperature-sensitive amphiphilic dendritic macromolecule based on tetraphenylethylene and preparation method thereof |
| CN112028819B (en) * | 2020-08-18 | 2021-12-10 | 中南大学 | Organic ligand compound of tetraphenyl ethylene terpyridine, coordination supermolecule, preparation and application thereof |
| CN112920117B (en) * | 2021-01-29 | 2022-12-20 | 上海工程技术大学 | Method for applying photosensitizer based on aggregation-induced emission in cell imaging and photodynamic therapy |
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