CN108299377A - A kind of preparation method for the adjustable tetraphenyl ethylene solid fluorescence dyestuff that shines - Google Patents
A kind of preparation method for the adjustable tetraphenyl ethylene solid fluorescence dyestuff that shines Download PDFInfo
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Abstract
The invention belongs to organic compound preparation technical fields, and the present invention relates to a kind of preparation method for the adjustable tetraphenyl ethylene solid fluorescence dyestuff that shines, the mechanism of preparation is：Hydrogen atom is more active on 2,2 ' dihydroxy benaophenonel hydroxyls, is first protected it with methoxy substitution.Using n-BuLi by diphenyl-methane methylene lithium salts, it is added 2,2 ' dimethoxy-benzophenones react, reaction product is dehydrated under the catalysis of p-methyl benzenesulfonic acid, it is reacted with different chain length saturated dihalide after hydrolyzing again, to which different chain length alkoxy bridge is introduced tetraphenyl ethylene adjacent phenyl rings α, tetraphenyl ethylene conformation adjusting is carried out using alkoxy bridge chain length difference, and then obtain the tetraphenyl ethylene dyestuff of different emission.
Description
Technical field
The invention belongs to organic compound preparation technical fields, and in particular to the luminous adjustable tetraphenyl ethylene solid fluorescence of one kind
The preparation method of dyestuff.
Background technology
Aggregation-induced emission is that organic fluorescent dye does not shine in unimolecule form or weak solution or light is very weak, poly-
Strong fluorescence can be sent out under collection or solid-state.This is because four phenyl ring pass through singly-bound and center in tetraphenyl ethylene in the solution
Double bond is connected, and phenyl ring singly-bound is freely rotatable, and then excited energy is caused mainly to return to ground state in the form of radiationless transition, and four
Styrene molecules do not shine；In solid-state or coherent condition, intermolecular distance reduces or molecule overlapping, the rotation of phenyl ring by
To limitation, and then shine.In gathering induced luminescence material, tetraphenyl ethylene molecular structure is simple, and synthetic modification is convenient, and has
There is excellent aggregation-induced emission performance, adjusts the method for modifying of tetraphenyl ethylene luminosity at present generally by changing substitution
The confession of base, electron-withdrawing ability, or by forming the methods of hydrogen bond, formation aggregation control aggregation extent etc. between molecule.It removes
By aggregation inducing, it shines outer, by the method for crystal engineering, control phenyl ring and conjugation of the ethylene double bond in crystal
Degree can also adjust shining for tetraphenyl ethylene material.But the method for crystal engineering is difficult to be carried out greatly to conjugated degree at present
Effective adjusting of range.
Invention content
For the above-mentioned prior art the problem of, it is an object of the present invention to provide the luminous adjustable four benzene second of one kind
The preparation method of alkene solid fluorescence dyestuff.Different chain length alkoxy is introduced into tetraphenyl ethylene adjacent phenyl rings α, obtains alkoxy bridge
Replace tetraphenyl ethylene, using different alkoxy bridge chain length and then adjusts tetraphenyl ethylene conformation, the substitution of different chain length alkoxy bridge
Tetraphenyl ethylene have different wave length maximum emission peak and different luminous intensities.
In order to solve the above technical problems, the technical scheme is that：
A kind of preparation method for the adjustable tetraphenyl ethylene solid fluorescence dyestuff that shines：
1) under in nitrogen protection, by α, α '-dihydroxy tetraphenyl ethylene and potassium carbonate are dissolved in dry acetone, are added
Dibromo alkane reacts after heating and obtains mixture A for a period of time；
2) with dichloromethane extraction step 1) obtained mixture A, merge organic phase, it will after being dried using anhydrous magnesium sulfate
Solvent removes；
3) use n-hexane/dichloromethane as mobile phase carry out column chromatography for separation, obtain white solid be shine can
Adjust tetraphenyl ethylene solid fluorescence dyestuff.
The acetone is solvent.
Preferably, α in step 1), α '-dihydroxy tetraphenyl ethylene, potassium carbonate, acetone, dibromo alkane ratio be：1mmol：
6-12mmol：30-50mL：1-3mmol；Temperature after heating is 50-70 DEG C；Reaction time is 12-24h.
Preferably, the dibromo alkane in step 1) is 1,2- Bromofumes, 1,3- dibromopropane, one in Isosorbide-5-Nitrae-dibromobutane
Kind.
Alkoxy bridge, which is obtained, by above step replaces tetraphenyl ethylene.When dibromo alkane is chemical combination prepared by 1,2- Bromofumes
The alkoxy bridge that object is n=2 replaces tetraphenyl ethylene, when dibromo alkane is the alcoxyl that compound prepared by 1,3- dibromopropanes is n=3
Ji Qiao replaces tetraphenyl ethylene, when dibromo alkane is that the alkoxy bridge that compound prepared by Isosorbide-5-Nitrae-dibromobutane is n=4 replaces four benzene second
Alkene.
The preparation method of α, α '-dihydroxy tetraphenyl ethylene
1) under the protection of nitrogen, by α, α '-dimethoxy tetraphenyl ethylenes are dissolved in dry dichloromethane, in a constant temperature
After degree lower stirring a period of time, mixture B is obtained；
2) Boron tribromide is added in mixture B, reacts arrive mixture C after a period of time at a certain temperature；
3) mixture C is poured into the deionized water of logical nitrogen deoxygenation, stirs to get mixture D；
4) mixture D is extracted with dichloromethane, merges organic phase, solvent is removed after being dried with anhydrous magnesium sulfate, is obtained
It is α, α '-dihydroxy tetraphenyl ethylenes to white solid.
Preferably, α in step 1), α '-dimethoxy tetraphenyl ethylene, dichloromethane, Boron tribromide ratio be 1mmol：
10-20mL：3-6mmol；Temperature is -70 DEG C -- 50 DEG C；Mixing time is 10-20min.
Preferably, reaction temperature is room temperature, reaction time 12-24h in step 2).
Preferably, it is 5-10min that the time is bubbled in step 3)；Mixing time is 1-2h.
The preparation method of α, α '-dimethoxy tetraphenyl ethylene
1) diphenyl-methane is dissolved in tetrahydrofuran, is cooled to certain temperature under nitrogen protection, just by n-BuLi
Hexane solution is added in mixture, and mixture E is obtained after reacting a period of time,
2) 2,2 '-dimethoxy-benzophenones are added in mixture E, temperature are risen into certain temperature, when reacting one section
Between after, be added ammonium chloride solution make reaction stop obtaining mixture F；
3) reaction mixture F is extracted with dichloromethane, dries and remove after obtained organic phase saturated common salt water washing
Solvent is removed, tertiary alcohol intermediate product is obtained；
4) intermediate product that step 3) obtains is placed in the flask with Dean-Stark water knockout drums, toluene, right is added
Toluenesulfonic acid is heated to certain temperature, after a period of time, divides water, mixture G is obtained after the completion of reaction；
5) sodium bicarbonate solution washing is added in mixture G, removes solvent after dry, uses the n-hexane of ethyl acetate
Column chromatography for separation is carried out as mobile phase, it is α, α '-dimethoxy tetraphenyl ethylenes to obtain white solid.
The toluene is solvent.
The toluenesulfonic acid is as acidic dehydration catalyst.
Preferably, temperature after cooling is -10-0 DEG C in step 1)；Reaction time is 1-2h.
Preferably, diphenyl-methane, n-BuLi, 2 in step 1), 2 '-dimethoxy-benzophenones, tetrahydrofuran ratio
For 1mmol：0.8-0.9mmol：0.6-0.8mmol：10-20mL.
Preferably, the temperature in step 2) after heating is 40-70 DEG C；Reaction time is 12-36h；The matter of ammonium chloride solution
It is 10% to measure score.
Preferably, intermediate product tertiary alcohol in step 4), toluene, p-methyl benzenesulfonic acid ratio be 1mmol:20-50mL:,
0.1-0.2mmol；Heating temperature is 120-140 DEG C；Reaction time is 4-6h.
Preferably, the mass fraction of sodium bicarbonate solution is 10% in step 5)；Acetic acid second in the n-hexane of ethyl acetate
The volume ratio of ester is 0.5-2%.
The preparation method of α, α '-dimethoxy-benzophenone
1), by α, α '-dihydroxy benaophenonels, potassium carbonate and iodomethane are dissolved in acetone, heat up under the protection of nitrogen,
Mixture H is obtained after reaction a period of time；
2) reaction mixture H is extracted with dichloromethane, merges organic phase, removes solvent after being dried with anhydrous magnesium sulfate
Go 3), use n-hexane as mobile phase carry out column chromatography for separation, it is α, α '-dimethoxy-benzophenones to obtain white solid.
Preferably, α in step 1), α '-dihydroxy benaophenonel, potassium carbonate, iodomethane and acetone ratio be 1mmol：
6-12mmol：2-5mmol：20-30mL；Temperature after heating is 50-70 DEG C；Reaction time is 12-24h.
The mechanism of preparation method of the present invention is as follows：
Hydrogen atom is more active on α, α '-dihydroxy benaophenonel hydroxyl, is first protected it with methoxy substitution.
Without other reactive hydrogen atoms in addition to the hydrogen atom in methylene bridge, we use on butyl lithium and methylene bridge diphenyl-methane
Atomic reaction of hydrogen, by diphenyl-methane lithium salts, further with α, α '-dimethoxy-benzophenones carry out nucleophilic addition obtain
To intermediate product, which is dehydrated under Catalyzed by p-Toluenesulfonic Acid obtains the tetraphenyl ethylene of dimethoxy substitution.After hydrolysis,
Hydroxyl can be led to the positions α of tetraphenyl ethylene adjacent phenyl rings.We are reacted with it using dibromo alkane, by two adjacent phenyl rings of tetraphenyl ethylene
The purpose for adjusting conformation is realized in cyclisation by alkoxy bridge chain length.
Beneficial effects of the present invention：
1) the adjustable tetraphenyl ethylene solid fluorescence dye structure of preparation is simple, synthesis is convenient, yield is high, gathers with excellent
Collect induced luminescence performance；
2) tool is prepared for there are three types of the adjustable tetraphenyl ethylene solid fluorescence dyestuff of chain length, is realized through bridge chain length minor section
The purpose of conformation, and then realize the purpose of adjustment luminescent properties；
3) the tetraphenyl ethylene solid fluorescence dye composition 5 prepared has apparent switching mode machinery luminosity.
Description of the drawings
The accompanying drawings which form a part of this application are used for providing further understanding of the present application, and the application's shows
Meaning property embodiment and its explanation do not constitute the improper restriction to the application for explaining the application.
Fig. 1 is the chemical equation that alkoxy bridge replaces tetraphenyl ethylene
Fig. 2 is the luminous schematic diagram of luminous adjustable tetraphenyl ethylene fluorescent dye
Fig. 3 is the fluorescent dye of tetraphenyl ethylene (1 in dimethyl sulfoxide/water mixed solvent：9) fluorescence schematic diagram
Specific implementation mode
It is noted that following detailed description is all illustrative, it is intended to provide further instruction to the application.Unless another
It indicates, all technical and scientific terms used herein has usual with the application person of an ordinary skill in the technical field
The identical meanings of understanding.
It should be noted that term used herein above is merely to describe specific implementation mode, and be not intended to restricted root
According to the illustrative embodiments of the application.As used herein, unless the context clearly indicates otherwise, otherwise singulative
It is also intended to include plural form, additionally, it should be understood that, when in the present specification using term "comprising" and/or " packet
Include " when, indicate existing characteristics, step, operation, device, component and/or combination thereof.
With reference to embodiment, the present invention is further described
Embodiment 1
The synthesis of compound 1 (2,2 '-dimethoxy-benzophenone) as shown in Figure 1
By 2,2 '-dihydroxy benaophenonels (0.6g, 3mmol), potassium carbonate (4.1g, 30mmol) is placed in 150mL round-bottomed bottles
In；The acetone of 60mL dryings, stirring to dissolving are added under nitrogen protection；Iodomethane (1.73g, 12mmol), which is added, will react temperature
Degree rises to 60 DEG C, the reaction was continued 12h；(3 × 50mL) is extracted with dichloromethane after reaction, merges organic phase；Using anhydrous
Solvent is removed after magnesium sulfate drying；Column chromatography for separation is carried out using n-hexane as mobile phase, obtains white solid, yield
95%.
Embodiment 2
The synthesis of compound 2 (2,2 '-dimethoxy tetraphenyl ethylene) as shown in Figure 1
Diphenyl-methane (0.5g, 3.0mmol) is placed in 50mL reactors；The four of 30mL dryings are added under nitrogen protection
Hydrogen furans；- 10 DEG C are cooled to, 10min is placed；1.0mL n-BuLis hexane solution (2.5mol/L) is added, reacts 1h；It will
2,2 '-dimethoxy-benzophenones (0.55g, 2.25mmol) are added in mixed solution；Reaction temperature is risen into 50 DEG C of reactions
24h；The ammonium chloride solution for being added 10% terminates reaction；(3 × 50mL) is extracted with dichloromethane, merges organic phase, is eaten with saturation
Salt water washing；Solvent is removed after being dried using anhydrous magnesium sulfate, obtains tertiary alcohol intermediate product；Intermediate product will be obtained to be placed in
In 150mL round-bottomed flasks with Dean-Stark water knockout drums, 80mL toluene is added；Addition p-methyl benzenesulfonic acid (57mg,
0.3mmol)；140 DEG C are warming up to, 4h is reacted；After the completion of reaction, 10% sodium bicarbonate solution washing is added, uses dichloromethane
It extracts (3 × 50mL), merges organic phase；Solvent is removed after being dried using anhydrous magnesium sulfate；Using containing ethyl acetate 0.5%
N-hexane carries out column chromatography for separation as mobile phase, obtains white solid, yield 65%.
Embodiment 3
The synthesis of compound 3 (2,2 '-dihydroxy tetraphenyl ethylene) as shown in Figure 1
Compound 2 (0.392g, 1.0mmol) is placed in 50mL reactors；10mL dryings are added under nitrogen protection
Dichloromethane, stirring to dissolving；- 65 DEG C are cooled to, 15min is stirred；The dichloromethane solution of 4.0mL Boron tribromides is added
(1.0mol/L), reactor is taken out, and is put to room temperature；12h is stirred at room temperature；100mL deionized waters are taken, 250mL round bottoms are placed in
In bottle；Nitrogen is bubbled 10min；Liquid in reactor is poured into round-bottomed bottle, nitrogen protection, stirs 1h；It is extracted with dichloromethane
(3 × 50mL) merges organic phase；Solvent is removed after being dried using anhydrous magnesium sulfate, obtains white solid, yield 90%.
Embodiment 4
The synthesis of compound 4 (n=2 alkoxy bridges replace tetraphenyl ethylene) as shown in Figure 1
Compound 3 (364mg, 1mmol) and potassium carbonate (1.38g, 10mmol) are placed in 150mL round-bottomed bottles；In nitrogen
The acetone of 50mL dryings, stirring to dissolving are added under protection；Glycol dibromide (0.28g, 1.5mmol) is added；It is warming up to 60
DEG C, react 12h；(3 × 50mL) is extracted with dichloromethane, merges organic phase；Solvent is removed after being dried using anhydrous magnesium sulfate；
Column chromatography for separation is carried out using n-hexane/dichloromethane (85/15) as mobile phase, obtains white solid, yield 30%.
Embodiment 5
The synthesis of compound 5 (n=3 alkoxy bridges replace tetraphenyl ethylene) as shown in Figure 1
Compound 3 (364mg, 1mmol) and potassium carbonate (1.38g, 10mmol) are placed in 150mL round-bottomed bottles；In nitrogen
The acetone of 50mL dryings, stirring to dissolving are added under protection；1,3- dibromopropanes (0.30g, 1.5mmol) are added；It is warming up to 60
DEG C, react 12h；(3 × 50mL) is extracted with dichloromethane, merges organic phase；Solvent is removed after being dried using anhydrous magnesium sulfate；
Column chromatography for separation is carried out using n-hexane/dichloromethane (80/20) as mobile phase, obtains white solid, yield 67%.
Embodiment 6
The synthesis of compound 6 (n=4 alkoxy bridges replace tetraphenyl ethylene) as shown in Figure 1
Compound 3 (364mg, 1mmol) and potassium carbonate (1.38g, 10mmol) are placed in 150mL round-bottomed bottles；In nitrogen
The acetone of 50mL dryings, stirring to dissolving are added under protection；1,4- dibromobutanes (0.32g, 1.5mmol) are added；It is warming up to 60
DEG C, react 12h；(3 × 50mL) is extracted with dichloromethane, merges organic phase；Solvent is removed after being dried using anhydrous magnesium sulfate；
Column chromatography for separation is carried out using n-hexane/dichloromethane (80/20) as mobile phase, obtains white solid, yield 92%.
A is compound 4 in Fig. 2, and B is compound 5, and C is compound 6, and D is compound 2；1 takes the photograph for natural crystal photo-beat, and 2
It is shot for natural light after crystal grinding to be shot under crystal ultraviolet light, 3,4 be to be shot under ultraviolet light after crystal is ground.
A is compound 4 in Fig. 3, and B is compound 5, and C is compound 6, and D is compound 2.
As shown in Figure 2, first be classified as compound 4, compound 5, compound 6 and compound 2 carried out under natural light it is micro-
The transparent state of sem observation；Compound 4, compound 5, compound 6 and compound 2 carry out under natural light after third is classified as grinding
Micro- sem observation is in powdered, is not transparent；Secondary series compound 4, compound 5, compound 6 and compound 2 are in ultraviolet light
Under micro- sem observation, compound 4 and compound 5 send out dim light, and compound 6 and compound 2 send out strong light；After 4th row grinding
Compound 4, compound 5, compound 6 and compound 2 micro- sem observation under ultraviolet light, compound 4 send out dim light, compound 5,
Compound 6 and compound 2 send out strong light.
When the chain length difference of adjustable tetraphenyl ethylene solid fluorescence dyestuff alkane prepared by the application known to Fig. 2 and Fig. 3,
The luminescent properties of fluorescent dye are significantly different, and crystal is polished, and luminescent properties are obviously different, and wherein compound 5 has bright
Aobvious switching mode machinery luminosity, so the application has reached introduces tetraphenyl ethylene adjacent phenyl rings by different chain length alkoxy
α, and then prepare the purpose of the tetraphenyl ethylene solid fluorescence dyestuff of different luminescent properties.By example 2 and embodiment 4,5,6 into
Row comparison, it is known that different chain length alkane prepared by the application introduces the tetraphenyl ethylene solid fluorescence of tetraphenyl ethylene adjacent phenyl rings α
Dyestuff has fluorescence regulating effect more better than open chain tetraphenyl ethylene solid fluorescence dyestuff.
The foregoing is merely the preferred embodiments of the application, are not intended to limit this application, for the skill of this field
For art personnel, the application can have various modifications and variations.Within the spirit and principles of this application, any made by repair
Change, equivalent replacement, improvement etc., should be included within the protection domain of the application.
Claims (10)
1. a kind of preparation method for the adjustable tetraphenyl ethylene solid fluorescence dyestuff that shines, it is characterised in that：The specific steps are：
1) under nitrogen protection, α, α '-dihydroxy tetraphenyl ethylene and potassium carbonate are dissolved in dry acetone, dibromo is added
Alkane reacts after heating and obtains mixture A for a period of time；
2) with dichloromethane extraction step 1) obtained mixture A, merge organic phase, by solvent after being dried using anhydrous magnesium sulfate
It removes；
3) n-hexane/dichloromethane is used to carry out column chromatography for separation as mobile phase, it is luminous adjustable four to obtain white solid
Styrene solid fluorescence dyestuff；
Preferably, the dibromo alkane is 1,2- Bromofumes, 1,3- dibromopropane, one kind in Isosorbide-5-Nitrae-dibromobutane.
2. a kind of preparation method of adjustable tetraphenyl ethylene solid fluorescence dyestuff that shines according to claim 1, feature exist
In：α in the step 1), α '-dihydroxy tetraphenyl ethylene, potassium carbonate, acetone, dibromo alkane ratio be：1mmol：6-12mmol：
30-50mL：1-3mmol；Temperature after heating is 50-70 DEG C；Reaction time is 12-24h.
3. a kind of preparation method of adjustable tetraphenyl ethylene solid fluorescence dyestuff that shines according to claim 1, feature exist
In：The preparation method of α, α '-dihydroxy tetraphenyl ethylene the specific steps are：
1) under the protection of nitrogen, by α, α '-dimethoxy tetraphenyl ethylenes are dissolved in dry dichloromethane, at a certain temperature
After stirring a period of time, mixture B is obtained；
2) Boron tribromide is added in mixture B, mixture C is obtained after reacting a period of time at a certain temperature；
3) mixture C is poured into the deionized water of logical nitrogen deoxygenation, stirs to get mixture D；
4) mixture D is extracted with dichloromethane, merges organic phase, solvent is removed after being dried with anhydrous magnesium sulfate, is obtained white
Color solid is α, α '-dihydroxy tetraphenyl ethylenes.
4. a kind of preparation method of adjustable tetraphenyl ethylene solid fluorescence dyestuff that shines according to claim 3, feature exist
In：α in the step 1), α '-dimethoxy tetraphenyl ethylene, dichloromethane, Boron tribromide ratio be 1mmol：10-20mL：
3-6mmol；Temperature is -70 DEG C -- 50 DEG C；Mixing time is 10-20min；Reaction temperature is room temperature, reaction in the step 2)
Time is 12-24h；It is 5-10min that the time is bubbled in the step 3)；Mixing time is 1-2h.
5. a kind of preparation method of adjustable tetraphenyl ethylene solid fluorescence dyestuff that shines according to claim 1, feature exist
In：The preparation method of α, α '-dimethoxy tetraphenyl ethylene the specific steps are：
1) diphenyl-methane is dissolved in tetrahydrofuran, is cooled to certain temperature under nitrogen protection, by the n-hexane of n-BuLi
Solution is added in mixture, and mixture E is obtained after reacting a period of time,
2) 2,2 '-dimethoxy-benzophenones are added in mixture E, temperature is risen into certain temperature, after reacting a period of time,
Ammonium chloride solution, which is added, makes reaction stop obtaining mixture F；
3) reaction mixture F is extracted with dichloromethane, dries and remove molten after obtained organic phase saturated common salt water washing
Agent obtains tertiary alcohol intermediate product；
4) intermediate product that step 3) obtains is placed in the flask with Dean-Stark water knockout drums, toluene is added, to toluene
Sulfonic acid is heated to certain temperature, after a period of time, divides water, mixture G is obtained after the completion of reaction；
5) sodium bicarbonate solution washing is added in mixture G, solvent is removed after dry, using ethyl acetate n-hexane as
Mobile phase carries out column chromatography for separation, and it is α, α '-dimethoxy tetraphenyl ethylenes to obtain white solid.
6. a kind of preparation method of adjustable tetraphenyl ethylene solid fluorescence dyestuff that shines according to claim 5, feature exist
In：Temperature after cooling is -10-0 DEG C in the step 1)；Reaction time is 1-2h；Middle diphenyl-methane in the step 1), just
Butyl lithium, 2,2 '-dimethoxy-benzophenones, tetrahydrofuran ratio be 1mmol：0.8-0.9mmol：0.6-0.8mmol：
10-20mL。
7. a kind of preparation method of adjustable tetraphenyl ethylene solid fluorescence dyestuff that shines according to claim 5, feature exist
In：Temperature in the step 2) after heating is 40-70 DEG C；Reaction time is 12-36h；The mass fraction of ammonium chloride solution is
10%；Intermediate product tertiary alcohol in the step 4), toluene, p-methyl benzenesulfonic acid ratio be 1mmol:20-50mL:0.1-
0.2mmol；Heating temperature is 120-140 DEG C；Reaction time is 4-6h；The mass fraction of sodium bicarbonate solution in the step 5)
It is 10%；The volume ratio of ethyl acetate is 0.5-2% in the n-hexane of ethyl acetate.
8. a kind of preparation method of adjustable tetraphenyl ethylene solid fluorescence dyestuff that shines according to claim 1, feature exist
In：The preparation method of 2,2 '-dimethoxy-benzophenones the specific steps are：
1) 2,2 '-dihydroxy benaophenonels, potassium carbonate and iodomethane are dissolved in acetone, are heated up under the protection of nitrogen, reacted
Mixture H is obtained after a period of time；
2) reaction mixture H is extracted with dichloromethane, merges organic phase, removes solvent after being dried with anhydrous magnesium sulfate；
3) n-hexane is used to carry out column chromatography for separation as mobile phase, it is 2,2 '-dimethoxy-benzophenones to obtain white solid.
9. a kind of preparation method of adjustable tetraphenyl ethylene solid fluorescence dyestuff that shines according to claim 8, feature exist
In：2,2 '-dihydroxy benaophenonels in the step 1), potassium carbonate, iodomethane and acetone ratio be 1mmol：6-12mmol：
2-5mmol：20-30mL；Temperature after heating is 50-70 DEG C；Reaction time is 12-24h.
10. it is according to claim 1 it is a kind of shine adjustable tetraphenyl ethylene solid fluorescence dyestuff its organic optoelectronic device,
The application of bioprobe, chemical sensitisation and stimuli responsive off-color material field.
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