CN106634969A - Tetraphenyl ethylene based fluorescent compound as well as preparation method and application thereof - Google Patents
Tetraphenyl ethylene based fluorescent compound as well as preparation method and application thereof Download PDFInfo
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- CN106634969A CN106634969A CN201611269867.2A CN201611269867A CN106634969A CN 106634969 A CN106634969 A CN 106634969A CN 201611269867 A CN201611269867 A CN 201611269867A CN 106634969 A CN106634969 A CN 106634969A
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Abstract
The invention discloses a tetraphenyl ethylene based fluorescent compound as well as a preparation method and an application thereof. A structure of the fluorescent compound is represented as a formula (I). The fluorescent compound is prepared through steps as follows: tetraphenyl ethylene glycollic acid is taken as a raw material and subjected to condensation with glycerin monostearate, then an obtained reaction product reacts with succinic anhydride and subjected to ring opening, and the fluorescent compound is obtained. The fluorescent compound is composited with other phosphatidyl choline such as DPPC (dipalmitoyl phosphatidylcholine), DSPC (disaturated phosphatidylcholine) and DAPC (1,2-dilauroyl-sn-glycero-3-phosphocholine) and DSPE-PEG2000 (distearoyl-phosphatidylethanolamine-polyethylene glycol 2000) to form a temperature-sensitive fluorescent nanomaterial. The fluorescent nanomaterial comprises the raw materials in percentage by mass as follows: 5%-30% of a fluorescent compound I, 60%-90% of the phosphatidyl choline and 1%-10% of DSPE-PEG2000. Nanoparticles are ultrasonically formed with a filming-rehydration method, the average particle size is about 50 nm, and the obtained temperature-sensitive fluorescent nanomaterial has good temperature response performance and has potential application value in the field of drug release.
Description
Technical field
The present invention relates to field of nano material preparation, and in particular to a kind of fluorescent chemicalses based on tetraphenyl ethylene and
Its preparation method and application.
Background technology
Traditional fluorescent chemicalses major part has higher fluorescence quantum yield in weak solution, and in high concentration or
Under coherent condition, fluorescent weakening is even quenched, and this aggregation inducing quenching effect greatly limit their range of application.Aggregation
Induced luminescence phenomenon is that this loyal academician was reported in calendar year 2001 by Tang, causes the extensive concern of scientific circles.Pentapheneyl sila ring
The compounds such as pentadiene, tetraphenyl ethylene, bigcatkin willow azine, triarylamine are found to have good aggregation inducing effect.
Tetraphenyl ethylene compound is the aggregation-induced emission compound of a quasi-representative, its under aggregation or solid state,
Rotating freely for four phenyl ring is suppressed and sends 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 is text simultaneously
Offer and report which can be used for the transport of antitumor drug as biological medicine nano material, and the release position of medicine can be monitored
Put and effect.
The content of the invention
It is an object of the invention to provide a kind of fluorescent chemicalses based on tetraphenyl ethylene and its preparation method and application.
The technical scheme is that：
A kind of fluorescent chemicalses based on tetraphenyl ethylene, with the structure shown in formula (I)：
The preparation method of the above-mentioned fluorescent chemicalses based on tetraphenyl ethylene, comprises the steps：
(1) be that compound 1 is dissolved in dichloromethane by tetraphenyl ethylene glycolic, add thionyl chloride, thionyl chloride with
The ratio of the amount of the material of compound 1 is 1～5:1, and be added dropwise over DMF, it 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；Will mixing
Solution is added drop-wise to containing in the glyceryl monostearate i.e. dichloromethane solution of compound 2 and organic base, compound 1, compound 2
Ratio with the amount of the material of organic base three is 1～2:1:1～3, it is stirred at room temperature 24～48 hours, adds saturation after completion of the reaction
Saline solution, is then extracted with ethyl acetate, with anhydrous sodium sulfate drying 1～2 hour, is filtered to remove solid sodium sulfate, molten
Liquid vacuum rotary steam, crude product column chromatography obtain milky oily compound i.e. compound 3；Shown in its reaction equation such as formula (II)：
(2) it is that compound 4 is dissolved in solvent by compound 3 and succinic anhydride, the amount of the material of compound 4 and compound 3
Ratio be 1～10:1, and organic base is added, it is stirred at room temperature 24～48 hours, adds saturated aqueous common salt, Ran Houyong after completion of the reaction
Ethyl acetate is extracted, and with anhydrous sodium sulfate drying 1～2 hour, is filtered to remove solid sodium sulfate, solution decompression revolving, slightly
Product column chromatography obtains milky oily compound, i.e., the fluorescent chemicalses (fluorescent chemicalses I) shown in formula (I)；Its reaction equation
As shown in formula (III)：
Each compound is distinguish between with sequence number below each compound in reaction equation above.
Further, the ratio of the amount of the material of compound 2 and compound 1 is preferably 2:1.
Further, in step (1), the preferred triethylamine of described organic base.
Further, in step (2), the preferred anhydrous methylene chloride of described solvent.
Further, in step (2), the preferred DMAP of described organic base (DMAP).
The method that above-mentioned fluorescent chemicalses are applied to temperature sensitive fluorescent material, comprises the steps：
1) prepare the chloroformic solution for being dispersed with fluorescent chemicalses I, phosphatidyl choline, DSPE-PEG2000；
2) mixed material sample solution makes thin film；
3) water bath sonicator makes nanoparticle；
4) study wavelength of fluorescence variation with temperature situation.
Specific application process is as follows：
1) fluorescent chemicalses 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 for taking fluorescent chemicalses I, phosphatidyl choline, DSPE-PEG2000 respectively forms mixed in round-bottomed flask
Close solution, vacuum rotary steam 30～45 minutes；
3) in round-bottomed flask deionized water, 30～45min of water bath sonicator is added to place 12～36 hours；
4) take step 3) 8～15 times of resulting solution dilution, under 325nm excitations, observation fluorescence intensity is with temperature
Elevated situation of change.
Further, step 2) mixed solution in, fluorescent chemicalses I, phosphatidyl choline, the quality hundred of DSPE-PEG2000
Divide ratio respectively 5～30%, 60～90% and 1～10%.
Further, described phosphatidyl choline is dipalmitoyl phosphatidyl choline (DPPC), distearoyl phosphatidylcholine
(DSPC), in two Semen arachidis hypogaeae phosphatidyl cholines (DAPC) one or more.
The beneficial effects of the present invention is：
(1) present invention is ultrasonically formed nanoparticle using thin film aquation method, and particle diameter average-size is in 50nm or so, gained material
Material category aggregation-induced emission section bar material, concentration are bigger, and fluorescence is stronger, can greatly improve its range of application and applied environment.
(2) the temperature sensitive fluorescent material that the present invention is provided is good to temperature-responsive, raises with temperature, and 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, at 25,38,40,42,44,46,48,50 DEG C
Fluorescence intensity, top-down curve (being defined by peak) correspond to the temperature for gradually rising respectively.
Fig. 3 be the embodiment of the present invention 2, the fluorescence under 325nm excitations, at 38,40,42,44,46,48,50 DEG C
Intensity, top-down curve (being defined by peak) correspond to the temperature for gradually rising respectively.
Fig. 4 be the embodiment of the present invention 2, the fluorescence under 325nm excitations, at 38,40,42,44,46,48,50 DEG C
Intensity, top-down curve (being defined by peak) correspond to the temperature for gradually rising respectively.
Wherein, in Fig. 2 to Fig. 4, abscissa represents wavelength (wavelength), and vertical coordinate represents intensity (intensity).
Specific embodiment
The present invention is done below by way of specific embodiment and further described in detail, but this should not be interpreted as in the present invention
The scope for stating theme is only limitted to below example.All technologies realized based on the above of the present invention belong to the present invention's
Scope.
Instrument of the present invention and reagent：
Nuclear magnetic resonance analyser：Bruker AV-II 500MHz NMR, TMS are internal standard, CDCl3For solvent.
Agents useful for same be commercially available chemistry it is pure or analyze it is pure.
Embodiment 1
The synthesis of fluorescent chemicalses of the present invention
Fluorescent material of the present invention to prepare approach as follows：
(1)
2mmol compounds 1 are dissolved in 10mL dichloromethane, the material of thionyl chloride, thionyl chloride and compound 1 is added
Amount ratio be 5:1, and add a drop DMF, it 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 solutions of 1mmol glyceryl monostearates and 2mmol triethylamines, 48 hours are stirred at room temperature, after completion of the reaction
Saturated aqueous common salt is added, is then extracted with ethyl acetate, with anhydrous sodium sulfate drying 2 hours, be then filtered to remove sulphuric acid
Sodium solid, solution decompression revolving, crude product column chromatography 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.
(2)
Compound 3 and succinic anhydride are dissolved in dichloromethane, the ratio of the amount of the material of the succinic anhydride and compound 3
For 10:1, and DMAP is added, it is stirred at room temperature 24 hours, adds saturated aqueous common salt after completion of the reaction, then uses second
Acetoacetic ester is extracted, and with anhydrous sodium sulfate drying 1 hour, is then filtered to remove solid sodium sulfate, and solution decompression revolving is thick to produce
Thing column chromatography obtains milky oily compound, i.e., the fluorescent chemicalses (fluorescent chemicalses 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
Response curve of the preparation and fluorescence intensity of the temperature sensitive fluorescent material with DSPC as primary raw material to temperature
Take the fluorescent chemicalses I chloroformic solutions of 0.23mL, the DSPC chloroformic solutions of 2.0mL, the DSPE- of 0.125mL
The chloroformic solution of PEG2000 in the round-bottomed flask of 25mL, vacuum rotary steam 30min；It is subsequently adding the deionized water of 2.5mL, water
Bath ultrasound 30min, stands 24 hours；The nanometer solution for taking 0.2mL is diluted to 2mL, determines fluorescence intensity and varies with temperature situation,
Fluorescence spectrophotometer records the change of fluorescence intensity at 475nm respectively.The measure that fluorescence intensity is varied with temperature in the present embodiment, its
Under 325nm excitations, the graph of a relation that fluorescence intensity is varied with temperature is as shown in Figure 2.
Embodiment 3
Response curve of the preparation and fluorescence intensity of the temperature sensitive fluorescent material with DAPC as primary raw material to temperature
Take the compound I chloroformic solutions of 0.23mL, 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；It is subsequently adding the deionized water of 2.5mL, water bath sonicator
30min, stands 24 hours；The nanometer solution for taking 0.2mL is diluted to 2mL, determines fluorescence intensity and varies with temperature situation, fluorescence light
Spectrometer records the change of fluorescence intensity at 475nm respectively.The measure that fluorescence intensity is varied with temperature in the present embodiment, its
Under 325nm excitations, the graph of a relation that fluorescence intensity is varied with temperature is as shown in Figure 3.
Embodiment 4
Response curve of the preparation and fluorescence intensity of the temperature sensitive fluorescent material with DPPC as primary raw material to temperature
Take the compound I chloroformic solutions of 0.23mL, 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；It is subsequently adding the deionized water of 2.5mL, water bath sonicator
30min, stands 24 hours；The nanometer solution for taking 0.2mL is diluted to 2mL, determines fluorescence intensity and varies with temperature situation, fluorescence light
Spectrometer records the change of fluorescence intensity at 475nm respectively.The measure that fluorescence intensity is varied with temperature in the present embodiment, its
Under 325nm excitations, the graph of a relation that fluorescence intensity is varied with temperature is as shown in Figure 4.
Claims (10)
1. a kind of fluorescent chemicalses based on tetraphenyl ethylene, it is characterised in that with the structure shown in formula (I)：
2. the preparation method of the fluorescent chemicalses based on tetraphenyl ethylene described in claim 1, it is characterised in that including following step
Suddenly：
(1) it is that compound 1 is dissolved in dichloromethane by tetraphenyl ethylene glycolic, adds thionyl chloride, thionyl chloride and compound 1
Material amount ratio be 1～5:1, and DMF is added dropwise over, it is heated to reflux 3～8 hours, then decompression rotation
Volatile solvent is evaporated off and obtains acid chloride intermediate, add anhydrous methylene chloride and obtain mixed solution；By mixed solution slowly
It is added drop-wise to containing in the glyceryl monostearate i.e. dichloromethane solution of compound 2 and organic base, compound 1, compound 2 and has
The ratio of the amount of the material of machine alkali three is 1～2:1:1～3, it is stirred at room temperature 24～48 hours, adds saturated common salt after completion of the reaction
Water, is then extracted with ethyl acetate, with anhydrous sodium sulfate drying 1～2 hour, is filtered to remove solid sodium sulfate, and solution subtracts
Pressure revolving, crude product column chromatography obtain milky oily compound i.e. compound 3；Shown in its reaction equation such as formula (II)：
(2) it is that compound 4 is dissolved in solvent by compound 3 and succinic anhydride, the ratio of the amount of the material of compound 4 and compound 3
For 1～10:1, and organic base is added, it is stirred at room temperature 24～48 hours, adds saturated aqueous common salt after completion of the reaction, then uses acetic acid
Ethyl ester is extracted, and with anhydrous sodium sulfate drying 1～2 hour, is filtered to remove solid sodium sulfate, solution decompression revolving, crude product
Column chromatography obtains milky oily compound, as fluorescent chemicalses I；Shown in its reaction equation such as formula (III)：
3. the preparation method of the fluorescent chemicalses based on tetraphenyl ethylene according to claim 2, it is characterised in that step
(1) in, the ratio of the amount of the material of compound 2 and compound 1 is 2:1.
4. the preparation method of the fluorescent chemicalses based on tetraphenyl ethylene according to claim 2, it is characterised in that step
(1) organic base described in is triethylamine.
5. the preparation method of the fluorescent chemicalses based on tetraphenyl ethylene according to claim 2, it is characterised in that step
(2) organic solvent described in is dichloromethane.
6. the preparation method of the fluorescent chemicalses based on tetraphenyl ethylene according to claim 2, it is characterised in that step
(2) organic base described in is DMAP.
7. application of the fluorescent chemicalses described in claim 1 in temperature sensitive response fluorescent material.
8. application of the fluorescent chemicalses according to claim 7 in temperature sensitive response fluorescent material, it is characterised in that include
Following steps：
Fluorescent chemicalses I, phosphatidyl choline, the chloroformic solution of DSPE-PEG2000 are prepared, the concentration of three is 1～1.5mg/
ML, then three kinds of solution formation mixed solutions are taken respectively, 30～45min of vacuum rotary steam is subsequently adding deionized water, water bath sonicator 30
～45min, then place 12～36 hours, then determine the wavelength of fluorescence under condition of different temperatures.
9. application of the fluorescent chemicalses according to claim 8 in temperature sensitive response fluorescent material, it is characterised in that mixing
In solution, fluorescent material I, phosphatidyl choline, DSPE-PEG2000 mass percent be respectively 5～30%, 60～90% and 1～
10%.
10. application of the fluorescent chemicalses according to claim 8 in temperature sensitive response fluorescent material, it is characterised in that institute
The phosphatidyl choline stated is dipalmitoyl phosphatidyl choline, distearoyl phosphatidylcholine, in two Semen arachidis hypogaeae phosphatidyl cholines
One or more.
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| CN112920117A (en) * | 2021-01-29 | 2021-06-08 | 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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| CN112920117A (en) * | 2021-01-29 | 2021-06-08 | 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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