CN105111102B - A kind of Toluylene nitrile derivative and its preparation method and application - Google Patents
A kind of Toluylene nitrile derivative and its preparation method and application Download PDFInfo
- Publication number
- CN105111102B CN105111102B CN201510428702.4A CN201510428702A CN105111102B CN 105111102 B CN105111102 B CN 105111102B CN 201510428702 A CN201510428702 A CN 201510428702A CN 105111102 B CN105111102 B CN 105111102B
- Authority
- CN
- China
- Prior art keywords
- formula
- nitrile derivative
- amine intermediate
- toluylene
- toluylene nitrile
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Abstract
The invention provides Toluylene nitrile derivative shown in a kind of formula (I), its preparation method is：4 boric acid triphenylamines shown in p-bromobenzaldehyde shown in formula (II) and formula (III) are through triphen amine intermediate shown in Suzuki reaction generation formula (IV)s；Triphen amine intermediate shown in formula (IV) generates the Toluylene nitrile derivative with 4 methoxy cyanophenyls shown in formula (V) through Knoevenagel condensation reactions again；The characteristics of power stimuli responsive fluorescent switch performance of Toluylene nitrile derivative of the present invention has that contrast is high, can voluntarily recovered, cyclicity is good, and synthetic method is simple, it stimulates fluorescent switch material to can be applied to the fields such as fluorescent switch, sensor, storage and display as reversible force；
Description
(1) technical field
Fluorescent switch material is stimulated the present invention relates to a kind of Toluylene nitrile derivative and preparation method thereof and as reversible force
The application of material, it is adaptable to sensor, false proof, storage and display.
(2) background technology
The phenomenon that fluorescence color changes when material is applied in mechanical force referred to as pressure induced discoloration, with pressure mutagens
The material of color phenomenon at least has the stable state or metastable state accumulation mode of two kinds of influences that are stressed.After being stimulated by power, point
Sub- inertial forces change, and cause packing of molecules mode to change so that material becomes another from a kind of ordered structure
Orderly or partial order, disordered structure are planted, the photophysical property of material changes therewith.Then by the processing such as heating, solvent
Afterwards, the accumulation mode of molecule can revert to it is original, realize fluorescence color change invertibity.At present to existing with piezallochromy
The research of elephant focuses primarily upon small molecule, oligomer, liquid crystal and doped polymer this several class, and the state scientist such as the U.S., Japan is
It must compare deeply through studying.
(J.Am.Chem.Soc., 2007,129 such as Yasuhiko Sagara:1520-1521) synthesize and be found that four
The pyrene derivatives that individual N- hexyls paraphenylene terephthalamide base is constituted, when being stimulated by power, material becomes green by the blue-fluorescence of script
Color fluorescence, can be changed into blue-fluorescence again after heating.This be due between molecule between phenyl ring and pyrene ring the change of torsion angle and
The change of the ratio of clustered pattern and hydrogen bond, the final fluorescence color for causing material changes.
(the Asian J.Chem., 2011,6 (3) such as Chi Zhenguo:Tetraphenyl ethylene derivative 808-811) has been synthesized, has worked as material
When being stimulated by power, the fluorescence color of solid becomes yellow by original green, is reverted to after heating original
Strong green fluorescence.This is due to the space steric effect between aromatic ring so that all or part of space structure of molecule is turned round
It is bent.Because the space structure of distortion causes pi-pi bond reaction force attenuation, after forces are applied, molecular conformation is planarized or divided
Son sliding so that conjugated degree increase, fluorescence color changes.
However, the reversible piezochromic phenomenon reported at present is mainly the material fluorescence color transformation under external force effect, and
The fluorescence color of rare pressure controllable and the change of intensity；In addition, realize that reversible temperature is generally higher than 100 DEG C
(J.Am.Chem.Soc.2010,132,13675-13683), so as to significantly limit the application of such material.Controllable outer
Power is realized the controllable transformation of fluorescence color and voluntarily recovered after the stimulation of removal external force under stimulating, exist in actual life extensive
Application value.
(3) content of the invention
First purpose of the present invention is to provide a kind of talan with reversible force stimuli responsive fluorescent switch performance
Carbonitrile derivatives, it has, and contrast is high, can voluntarily recover, the characteristics of cyclicity is good.
Second object of the present invention is to provide a kind of method for simply preparing the Toluylene nitrile derivative.
Third object of the present invention, which is the Toluylene nitrile derivative as reversible force, stimulates fluorescent switch material to exist
Prepare the application in reversible force stimuli responsive fluorescent switch device.
To achieve the above object, the present invention is adopted the following technical scheme that：
A kind of Toluylene nitrile derivative shown in formula (I)：
Described Toluylene nitrile derivative is in the case of stress, because molecule conformation transition causes fluorescence intensity change
And reversible force stimuli responsive Enhancement of Fluorescence is presented, i.e.,：Under external force stimulation a variety of fluorescence are converted to from a kind of fluorescent emission
Emission state, the fluorescent state that can be returned to before non-stress through the post-stimulatory material of external force.
Specifically, described Toluylene nitrile derivative is after by the effect of 1atm~12.09GPa pressure, in uviol lamp
Under green fluorescence before not pressing become the fluorescent orange after being pressurized until red fluorescence, high with contrast, fluorescence color turns
The characteristics of becoming many.
The fluorescent switch performance of described Toluylene nitrile derivative (I) can voluntarily be recovered by release mode, such as exist
After the effect of 1atm~12.09GPa pressure, described Toluylene nitrile derivative (I) is green glimmering before not pressing under uviol lamp
Light becomes the fluorescent orange after being pressurized until red fluorescence, then by described Toluylene nitrile derivative carry out 12.09GPa~
1atm releases are acted on, and it can voluntarily return to original green fluorescence before not exerting pressure under uviol lamp.
In addition, the characteristics of fluorescent switch performance of described Toluylene nitrile derivative (I) also has pressure controllable：In warp
After the power stimulation-self- recoverage circulation for crossing quantitatively pressure, with good color transition.
Present invention also offers the preparation method of the Toluylene nitrile derivative shown in a kind of formula (I), described preparation side
Method is：The 4- boric acid triphenylamine shown in p-bromobenzaldehyde and formula (III) shown in formula (II) is through Suzuki reaction generation formula (IV)s
Shown triphen amine intermediate；Triphen amine intermediate shown in formula (IV) is passed through with the 4- methoxy cyanophenyls shown in formula (V) again
Toluylene nitrile derivative shown in Knoevenagel condensation reactions generation formula (I).
Specifically, a kind of preparation method of the Toluylene nitrile derivative shown in formula (I), the preparation method is by following step
It is rapid to carry out：
(1) under nitrogen protection, 4- boric acid triphenylamines are in organic solvent shown in p-bromobenzaldehyde shown in formula (II) and formula (III)
In, in catalyst Pd [P (C6H5)3]4In the presence of (tetrakis triphenylphosphine palladium) and alkaline matter, 16~48h of back flow reaction, it
Reaction solution is post-treated afterwards, obtains triphen amine intermediate shown in formula (IV)；
The organic solvent is toluene/tetrahydrofuran volume ratio 1：0.5~1 mixed liquor；The alkaline matter is carbonic acid
Sodium or potassium carbonate；P-bromobenzaldehyde shown in the formula (II) and 4- boric acid triphenylamine shown in formula (III), catalyst Pd [P
(C6H5)3]4, alkaline matter the ratio between the amount for the material that feeds intake be 1：0.8~1.2：0.01~0.03：1.2~2；
(2) in solvent chromatographic ethanol, 4- shown in triphen amine intermediate shown in the formula (IV) that step (1) is obtained and formula (V)
Methoxy cyanophenyl is separated out, filtering, filter cake is washed under the catalytic action of sodium methoxide in reacting at room temperature solid in 3~5h, reaction system
Wash, dry after, obtain Toluylene nitrile derivative shown in formula (I)；
The ratio between amount for the material that feeds intake of 4- methoxy cyanophenyls shown in triphen amine intermediate shown in the formula (IV) and formula (V)
For 0.8~1.2：1；The sodium methoxide is 1 with the ratio between amount for the material that feeds intake of triphen amine intermediate shown in formula (IV)：5~20.
In preparation method step (1) of the present invention, the volume of the organic solvent (in terms of toluene therein) is recommended to use
Amount is calculated as 20~35mL/g with the quality of p-bromobenzaldehyde shown in formula (II).
In step (1), the method for the reaction solution post processing is：After reaction terminates, reaction solution is cooled to room temperature, depressurizes dense
Chloroform extraction is used after contracting, extraction gained organic phase is washed through saturated aqueous sodium carbonate respectively, saturated common salt water washing, nothing
Water magnesium sulfate is dried, filtering, takes filtrate to be concentrated under reduced pressure, gained concentrate carries out silica gel column chromatography separation, with petroleum ether/chlorine
Imitative volume ratio 150：1 mixed liquor is eluant, eluent, collects the eluent containing target compound, is evaporated off drying after solvent, obtains formula
(IV) intermediate of triphen amine shown in.
In step (2), recommend the volumetric usage of the solvent chromatographic ethanol be calculated as 30 with the quality of 4- methoxy cyanophenyls~
50mL/g。
Specific optimal, the preparation method for recommending the Toluylene nitrile derivative shown in the formula (I) is：
(1) under nitrogen protection, by 4- boric acid triphenylamine, catalyst Pd shown in p-bromobenzaldehyde shown in formula (II), formula (III)
[P(C6H5)3]4It is dissolved in toluene/tetrahydrofuran volume ratio 1：In 0.5~1 mixed liquor, 2.0mol/L sodium carbonate is then added
The aqueous solution or 2.0mol/L wet chemicals, 16~48h of back flow reaction, afterwards reaction solution be cooled to room temperature, after being concentrated under reduced pressure
With chloroform extraction, extraction gained organic phase is washed through saturated aqueous sodium carbonate respectively, saturated common salt water washing, anhydrous sulphur
Sour magnesium is dried, filtering, takes filtrate to be concentrated under reduced pressure, gained concentrate carries out silica gel column chromatography separation, with petroleum ether/chloroform body
Product compares 150：1 mixed liquor is eluant, eluent, collects the eluent containing target compound, is evaporated off drying after solvent, obtains formula (IV)
Shown triphen amine intermediate；P-bromobenzaldehyde shown in the formula (II) and 4- boric acid triphenylamine, catalyst Pd shown in formula (III)
[P(C6H5)3]4, sodium carbonate or potassium carbonate the ratio between the amount for the material that feeds intake be 1：0.8~1.2：0.01~0.03：1.2~2；
(2) dissolving of 4- methoxy cyanophenyls shown in triphen amine intermediate shown in the formula (IV) for obtaining step (1) and formula (V)
In chromatographic ethanol, sodium methoxide is then added, is reacted at room temperature to there is precipitation to generate, then stand under the conditions of being placed in -20~25 DEG C
Precipitation, separates out solid particle, until there is no the generation of new solid particle, reaction system filtering, filter cake is washed with absolute ethyl alcohol
After dry, obtain Toluylene nitrile derivative shown in target product formula (I).
The present invention is derived by nuclear magnetic resonance (NMR), gas chromatography mass spectrometry (GC-MS), elemental analysis talan nitrile
Thing (I), Toluylene nitrile derivative (I) crystal structure is characterized by X-ray diffraction (XRD), calorimetric is scanned by differential
Method (DSC) tests its structure change temperature transition point and crystal property, and its surface topography is observed by ESEM (SEM), leads to
Cross uv-visible absorption spectroscopy and fluorescence spectrum characterization its photophysical property.
There is Toluylene nitrile derivative (I) of the present invention reversible force to stimulate fluorescent switch performance, therefore can be used as one
Planting reversible force stimulates fluorescent switch material, can be specifically for preparing reversible force stimuli responsive fluorescent switch device, for example, described two
The crystalline solid or powder solid of styrene carbonitrile derivatives (I), can coat hexichol second by existing film technique in substrate
The fluorescent switch device with power stimuli responsive performance is made in the mode of alkene carbonitrile derivatives film.
It is described that the specific method of Toluylene nitrile derivative film is coated for example in substrate by existing film technique：
Toluylene nitrile derivative is dissolved in dichloromethane, it is 10 to be prepared into Toluylene nitrile derivative concentration-2Mol/L dichloro
In dichloromethane, the spray gun for being positioned over a diameter of 0.2mm and being connected with air compressor, by spray gun by the solution to dry
Net quartz plate is sprayed, and is treated that solvent volatilizees, that is, is obtained Toluylene nitrile derivative film.
Compared with prior art, the beneficial effects of the present invention are：Have power stimuli responsive glimmering the invention provides one kind
The organic molecule Toluylene nitrile derivative (I) of photoswitch performance, the power stimuli responsive of the Toluylene nitrile derivative (I)
The characteristics of fluorescent switch performance has that contrast is high, can voluntarily recovered, cyclicity is good, and synthetic method is simple, it is as reversible
Power stimulates fluorescent switch material to can be applied to the fields such as fluorescent switch, sensor, storage and display.
(4) illustrate
Fig. 1 be in the embodiment of the present invention 5 Toluylene nitrile derivative solid powder (I) after normal pressure grinding under uviol lamp
Photo and its fluorescence spectrum；
Fig. 2 be in the embodiment of the present invention 6 Toluylene nitrile derivative solid powder (I) after controllable ration force, and
Photo after controllable ration release under uviol lamp；
Fig. 3 be in the embodiment of the present invention 6 Toluylene nitrile derivative solid powder (I) after controllable ration force, and
Fluorescence spectrum after controllable ration release；
Fig. 4 is power stimulation-self- recoverage circulation Raman light spectrality of Toluylene nitrile derivative (I) in the embodiment of the present invention 7
Energy.
(5) embodiment
Technical scheme is described further with specific embodiment below, but protection scope of the present invention is not limited
In this.
The active force that Toluylene nitrile derivative (I) and fluorescent switch device are subject in the embodiment of the present invention about 1atm~
Between 12.09GPa.
Embodiment 1
By p-bromobenzaldehyde (II) 0.92g (5mmol), 4- boric acid triphenylamine (III) 1.73g (6mmol), four (triphenyls
Phosphine) palladium 0.11g (0.1mmol) is dissolved in toluene 50mL/ tetrahydrofuran 30mL mixed solutions, add aqueous sodium carbonate (2.0M,
3mL).Under nitrogen atmosphere, 90 DEG C of reaction 36h are warming up to.Reaction solution is cooled down, and removes under reduced pressure after solvent, (50mL is extracted with chloroform
× 3) secondary, merge organic phase, it is finally dry with anhydrous magnesium sulfate respectively through saturated aqueous sodium carbonate and saturated common salt water washing
It is dry.Filtering, filtrate is through being concentrated under reduced pressure, and residue is separated with silica gel column chromatography, and eluant, eluent is that the volume ratio of petroleum ether/chloroform is
150/1 mixed solvent, collects the eluent containing target compound, removes under reduced pressure and is dried after solvent, obtains yellow powder product
Triphen amine intermediate (IV) 1.16g, yield is 75%.The structural confirmation of material is characterized as below：1H NMR(500MHz,DMSO)
δ 10.03 (s, 1H), 7.97 (d, J=8.4Hz, 2H), 7.88 (d, J=8.3Hz, 2H), 7.75-7.69 (m, 2H), 7.40-
7.33(m,4H),7.15–7.07(m,6H),7.06–7.02(m,2H).MS m/z:349.2
Embodiment 2
By p-bromobenzaldehyde (II) 0.92g (5mmol), 4- boric acid triphenylamine (III) 1.56g (4mmol), four (triphenyls
Phosphine) palladium 0.16g (0.15mmol) is dissolved in toluene 40mL/ tetrahydrofuran 25mL mixed solutions, adds aqueous sodium carbonate
(2.0M, 3mL).Under nitrogen atmosphere, 90 DEG C of reaction 24h are warming up to.Reaction solution is cooled down, and is removed under reduced pressure after solvent, molten with chloroform
Liquid extracts (30mL × 3), merges organic phase, respectively through saturated aqueous sodium carbonate and saturated common salt water washing, finally with anhydrous
Magnesium sulfate is dried.Filtering, filtrate is through being concentrated under reduced pressure, and residue is separated with silica gel column chromatography, and eluant, eluent is the body of chloroform/petroleum ether
Product collects the eluent containing target compound than the mixed solvent for 150/1, removes under reduced pressure and is dried after solvent, obtains yellow powder
Last product triphen amine intermediate (IV) 1.31g, yield is 70%.
Embodiment 3：
Weigh triphen amine intermediate (IV) 4.19g (12mmol), 4- methoxy cyanophenyls (V) 1.33g of above-mentioned synthesis
(10mmol) and sodium methoxide 0.06g (1mmol) are dissolved in 30ml chromatographic ethanols.Reaction 4h is stirred at room temperature, has treated a large amount of solid
Terminating reaction when body particle is separated out.Then reaction system is put into -20 DEG C of refrigerator overnights, filtered afterwards, filter cake ethanol rinse
Orange powder, i.e. target product talan nitrile derivative (I) 3.82g are obtained after (50mL × 3), natural drying, yield is
80%.The structural confirmation of material is characterized as below：1H NMR(500MHz,CDCl3):δ 7.93 (d, J=8.3Hz, 2H)；7.68(t,
J=16.2Hz, 2H)；7.64-7.61(m,2H)；7.52 (d, J=8.3Hz, 2H)；7.44(s,1H)；7.29 (t, J=7.6Hz,
4H)；7.10 (dd, J=47.4,5.5Hz, 8H)；6.99-6.95(m,2H)；3.86(s,3H).MS m/z:478.4
Embodiment 4
Weigh triphen amine intermediate (IV) 2.80g (8mmol), 4- methoxy cyanophenyls (V) 1.33g of above-mentioned synthesis
(10mmol) and sodium methoxide 0.03g (0.5mmol) are dissolved in 30ml chromatogram straight alcohols.Reaction 3h is stirred at room temperature, has treated big
Measure terminating reaction when solid particle is separated out.Then reaction system is put into -20 DEG C of refrigerator overnights, filtered afterwards, filter cake ethanol
Elute (50mL × 3), orange powder, i.e. target product talan nitrile derivative (I) 3.06g are obtained after natural drying, receive
Rate is 80%.
Embodiment 5
Toluylene nitrile derivative solid powder (I) 0.1g of the present invention spreads on quartz plate or is placed in mortar,
Strong green fluorescence is shown under uviol lamp, occurring without obvious fluorescence when being scraped shearing force or pestle effect by key changes colour,
External force is removed, part of the force still keeps strong green fluorescence.
Embodiment 6
Toluylene nitrile derivative solid powder (I) 0.1g of the present invention spreads over the ruby bottom surface of DAC instruments, quiet
State hydraulic coupling scope is to be carried out in 1atm~12.09GPa, pressure effect controllable in real time, it was observed that the fluorescence face under uviol lamp
Red red shift of the color from strong green to high wavelength, until being changed into red.The gradually release out of 12.09GPa~1atm pressure limits,
It was found that sample reverts to original strong green fluorescence from red gradually blue shift under uviol lamp.
Embodiment 7
Stressed Toluylene nitrile derivative (I) will not be applied, pressurization unloads the sample for being depressed into 1atm after causing 12.09GPa,
Raman test is done under identical Variable Conditions, it is found that both Raman spectrums are almost overlapping consistent, illustrates that sample can with good
Inverse cycle performance and recycling performance.
Claims (8)
1. a kind of Toluylene nitrile derivative shown in formula (I) as a kind of reversible force stimulate fluorescent switch material prepare it is reversible
Application in power stimuli responsive fluorescent switch device, it is characterised in that described reversible force, which is stimulated, to be referred in static hydraulic force model
Enclose to carry out pressure effect controllable in real time in 1atm~12.09GPa；
The method of the application is：Take the crystalline solid or powder solid of the Toluylene nitrile derivative, by it is existing into
The fluorescent switch with power stimuli responsive performance is made in the mode that membrane technology coats Toluylene nitrile derivative film in substrate
Device；
2. application as claimed in claim 1, it is characterised in that the preparation of the Toluylene nitrile derivative shown in the formula (I)
Method is：The 4- boric acid triphenylamine shown in p-bromobenzaldehyde and formula (III) shown in formula (II) reacts production through Suzuki
(IV) the triphen amine intermediate shown in；Triphen amine intermediate shown in formula (IV) again with the 4- methoxybenzenes shown in formula (V)
Acetonitrile generates the Toluylene nitrile derivative shown in formula (I) through Knoevenagel condensation reactions；
3. application as claimed in claim 2, it is characterised in that the preparation of the Toluylene nitrile derivative shown in the formula (I)
Method is carried out as follows：
(1) nitrogen protection under, 4- boric acid triphenylamines shown in p-bromobenzaldehyde shown in formula (II) and formula (III) in organic solvent,
In catalyst Pd [P (C6H5)3]4In the presence of alkaline matter, 16~48h of back flow reaction, reaction solution is post-treated afterwards, obtains
To triphen amine intermediate shown in formula (IV)；
The organic solvent is toluene/tetrahydrofuran volume ratio 1：0.5~1 mixed liquor；The alkaline matter be sodium carbonate or
Potassium carbonate；P-bromobenzaldehyde shown in the formula (II) and 4- boric acid triphenylamine shown in formula (III), catalyst Pd [P (C6H5)3]4、
The ratio between amount for the material that feeds intake of alkaline matter is 1：0.8~1.2：0.01~0.03：1.2~2；
(2) in solvent chromatographic ethanol, 4- methoxies shown in triphen amine intermediate shown in the formula (IV) that step (1) is obtained and formula (V)
Base benzene acetonitrile is separated out, filtering, filter cake is washed under the catalytic action of sodium methoxide in reacting at room temperature solid in 3~5h, reaction system
Wash, dry after, obtain Toluylene nitrile derivative shown in formula (I)；
The ratio between amount for the material that feeds intake of 4- p-methoxybenzeneacetonitriles is shown in triphen amine intermediate shown in the formula (IV) and formula (V)
0.8~1.2：1；The sodium methoxide is 1 with the ratio between amount for the material that feeds intake of triphen amine intermediate shown in formula (IV)：5~20.
4. application as claimed in claim 3, it is characterised in that in step (1), the volume of the toluene in the organic solvent is used
Amount is calculated as 20~35mL/g with the quality of p-bromobenzaldehyde shown in formula (II).
5. as claimed in claim 3 apply, it is characterised in that in step (1), the method for the reaction solution post processing is：Instead
After should terminating, reaction solution is cooled to room temperature, chloroform extraction is used after being concentrated under reduced pressure, extraction gained organic phase is respectively through saturated carbon
Acid sodium aqueous solution washing, saturated common salt water washing, anhydrous magnesium sulfate are dried, filtering, take filtrate to be concentrated under reduced pressure, gained concentration
Thing carries out silica gel column chromatography separation, with petroleum ether/chloroform volume ratio 150：1 mixed liquor is eluant, eluent, collects chemical combination containing target
The eluent of thing, is evaporated off drying after solvent, obtains triphen amine intermediate shown in formula (IV).
6. application as claimed in claim 3, it is characterised in that in step (2), the volumetric usage of the solvent chromatographic ethanol with
The quality of 4- p-methoxybenzeneacetonitriles is calculated as 30~50mL/g.
7. application as claimed in claim 3, it is characterised in that the preparation of the Toluylene nitrile derivative shown in the formula (I)
Method is：
(1) under nitrogen protection, by 4- boric acid triphenylamine, catalyst Pd [P shown in p-bromobenzaldehyde shown in formula (II), formula (III)
(C6H5)3]4It is dissolved in toluene/tetrahydrofuran volume ratio 1：In 0.5~1 mixed liquor, 2.0mol/L sodium carbonates are then added
Solution or 2.0mol/L wet chemicals, 16~48h of back flow reaction, afterwards reaction solution be cooled to room temperature, used after being concentrated under reduced pressure
Chloroform extraction, extraction gained organic phase is washed through saturated aqueous sodium carbonate respectively, saturated common salt water washing, anhydrous slufuric acid
Magnesium is dried, filtering, takes filtrate to be concentrated under reduced pressure, gained concentrate carries out silica gel column chromatography separation, with petroleum ether/chloroform volume
Than 150：1 mixed liquor is eluant, eluent, collects the eluent containing target compound, is evaporated off drying after solvent, obtains formula (IV) institute
Show triphen amine intermediate；P-bromobenzaldehyde shown in the formula (II) and 4- boric acid triphenylamine shown in formula (III), catalyst Pd [P
(C6H5)3]4, sodium carbonate or potassium carbonate the ratio between the amount for the material that feeds intake be 1：0.8~1.2：0.01~0.03：1.2~2；
(2) 4- p-methoxybenzeneacetonitriles shown in triphen amine intermediate shown in the formula (IV) for obtaining step (1) and formula (V) are dissolved in
In chromatographic ethanol, then add sodium methoxide, react at room temperature to there is precipitation to generate, then stand under the conditions of being placed in -20~25 DEG C it is heavy
Form sediment, separate out solid particle, until there is no the generation of new solid particle, reaction system filtering, after filter cake is washed with absolute ethyl alcohol
Dry, obtain Toluylene nitrile derivative shown in target product formula (I).
8. application as claimed in claim 1, it is characterised in that described that hexichol is coated in substrate by existing film technique
The method of ethene carbonitrile derivatives film is：Toluylene nitrile derivative is dissolved in dichloromethane, talan nitrile is prepared into
Derivatives concentration is 10-2Mol/L dichloromethane solution, is positioned over a diameter of 0.2mm and the spray being connected with air compressor
In rifle, the solution is sprayed to clean quartz plate by spray gun, treats that solvent volatilizees, that is, obtains talan nitrile derivative
Thing film.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510428702.4A CN105111102B (en) | 2015-07-20 | 2015-07-20 | A kind of Toluylene nitrile derivative and its preparation method and application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510428702.4A CN105111102B (en) | 2015-07-20 | 2015-07-20 | A kind of Toluylene nitrile derivative and its preparation method and application |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105111102A CN105111102A (en) | 2015-12-02 |
| CN105111102B true CN105111102B (en) | 2017-07-28 |
Family
ID=54659263
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510428702.4A Active CN105111102B (en) | 2015-07-20 | 2015-07-20 | A kind of Toluylene nitrile derivative and its preparation method and application |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105111102B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105152973B (en) * | 2015-08-20 | 2017-04-12 | 浙江工业大学 | Stilbene derivative as well as preparation method and application thereof |
| CN105294464B (en) * | 2015-08-20 | 2017-04-12 | 浙江工业大学 | Triphenylamine derivative and preparation method and application thereof |
| CN106278939A (en) * | 2016-08-11 | 2017-01-04 | 重庆大学 | The metachroic organic aggregate material of Fluorescence Increasing of one class Glassless |
| CN108530641B (en) * | 2018-02-01 | 2021-06-18 | 苏州大学 | Supermolecule polymer based on alpha-cyano diphenyl ethylene micromolecules and preparation method thereof |
| CN109134396A (en) * | 2018-08-20 | 2019-01-04 | 浙江工业大学 | The cyanobiphenyl ethylene compounds and the preparation method and application thereof of Z/E stable configuration under excitation state |
| CN112482263A (en) * | 2020-11-12 | 2021-03-12 | 招商局重庆交通科研设计院有限公司 | Overload detection road surface and vehicle overload detection method |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008540401A (en) * | 2005-05-05 | 2008-11-20 | メンパイル インク． | Chromophore capable of methacrylate-linked photoisomerization, its synthesis, and intermediates thereof |
| CN102911082B (en) * | 2012-06-08 | 2014-09-03 | 浙江工业大学 | Triphenylamine derivatives, and preparation method and application thereof |
| CN103102286B (en) * | 2012-12-08 | 2014-12-03 | 浙江工业大学 | Triphenylamine derivatives as well as preparation method and application thereof |
| CN103086918B (en) * | 2012-12-29 | 2014-11-12 | 浙江工业大学 | Toluylene nitrile derivative with D-A structure and synthesis method and application thereof |
| EP2806018A1 (en) * | 2013-05-20 | 2014-11-26 | The Procter & Gamble Company | Encapsulates |
| CN103641743A (en) * | 2013-12-09 | 2014-03-19 | 浙江工业大学 | Tristyrene nitrile derivative as well as preparation method and application thereof |
| CN103910652B (en) * | 2014-04-22 | 2016-04-27 | 安徽大学 | A kind of method of synthesis in water cyano group substituted styrene compound |
-
2015
- 2015-07-20 CN CN201510428702.4A patent/CN105111102B/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN105111102A (en) | 2015-12-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105111102B (en) | A kind of Toluylene nitrile derivative and its preparation method and application | |
| CN102911082B (en) | Triphenylamine derivatives, and preparation method and application thereof | |
| CN109651293B (en) | Benzothiadiazole benzyl cyanide derivative and preparation method and application thereof | |
| Bu et al. | Synthesis and piezochromic luminescence of aggregation-enhanced emission 9, 10-bis (N-alkylcarbazol-2-yl-vinyl-2) anthracenes | |
| CN107353243A (en) | The method for manufacturing thin film and application of a kind of triphenylamine derivative and its doping | |
| CN108947766B (en) | Fluorine-containing tetraphenylethylene compound and preparation method and application thereof | |
| CN109880084B (en) | Conjugated polymer containing triphenylamine structure and tetraphenylethylene unit, preparation method thereof and application thereof in electrochromism | |
| CN103102286A (en) | Triphenylamine derivatives as well as preparation method and application thereof | |
| CN110156749A (en) | A kind of bis- thienyl anthracene fluorescent chemicals of asymmetric 9,10- and its preparation method and application | |
| CN106588981A (en) | Temperature-sensitive fluorescent photochromic material with high quantum yield | |
| CN108997391B (en) | Preparation method of trimeric indenyl BODIPY-fullerene star-shaped compound | |
| CN111574578B (en) | Circular polarization luminescent material with intelligent response multicolor conversion and preparation method and application thereof | |
| CN105294464B (en) | Triphenylamine derivative and preparation method and application thereof | |
| CN113717231B (en) | AIE active force-induced light five-membered six-membered heterocyclic platinum complex, and preparation method and application thereof | |
| CN112010854B (en) | Trnano-ger's alkali derivative, preparation method thereof and test method for mechanical-induced fluorescence enhancement characteristics | |
| CN110128455B (en) | Preparation method of bornyl phenylethynyl BODIPY pH fluorescent probe | |
| CN109320459A (en) | A kind of phenanthro- imidazole derivative containing fluorenes, crystal and the preparation method and application thereof | |
| CN109134396A (en) | The cyanobiphenyl ethylene compounds and the preparation method and application thereof of Z/E stable configuration under excitation state | |
| CN109134345A (en) | 15- hexyl-tetraphenyl simultaneously [1,2-b] carbazole aromatic fused ring compound and its synthetic method | |
| CN112940006B (en) | Tetraphenyl ethylene-oxazine material and synthetic method and application thereof | |
| CN106631791B (en) | A kind of synthetic method of the hard and soft molecule of V-type based on pyrene and multiple-limb polyglycol chain | |
| CN117004039B (en) | Cadmium-based self-adaptive host and guest luminescent coordination polymer and preparation method and application thereof | |
| CN114656646B (en) | Synthetic method of diarylene COFs material and application of diarylene COFs material in light-operated adsorption | |
| CN115819281B (en) | Cyano-substituted p-phenylene ethylene derivative, preparation method and application | |
| CN115215891A (en) | Trimeric indenyl bridged perylene diimide-coumarin-boron dipyrrole star compound and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |