CN106083694A - A kind of 3,6 2 (anthraquinone 2 vinyl) N ethyl carbazole and preparation method thereof - Google Patents
A kind of 3,6 2 (anthraquinone 2 vinyl) N ethyl carbazole and preparation method thereof Download PDFInfo
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- CN106083694A CN106083694A CN201610372738.XA CN201610372738A CN106083694A CN 106083694 A CN106083694 A CN 106083694A CN 201610372738 A CN201610372738 A CN 201610372738A CN 106083694 A CN106083694 A CN 106083694A
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- ethyl carbazole
- carbazole
- anthraquinone
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- 0 C*1(C)c2ccccc2-c2c1cccc2 Chemical compound C*1(C)c2ccccc2-c2c1cccc2 0.000 description 2
- ATZWNZBRDFMMIW-UHFFFAOYSA-N NO[I](C=O)(ON)=O Chemical compound NO[I](C=O)(ON)=O ATZWNZBRDFMMIW-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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Abstract
The invention provides a kind of 3,6 two (anthraquinone 2 vinyl) N ethyl carbazole and preparation method thereof, belong to a kind of A π D π A electric charge in molecule transfer type, there is the compound of double fluorescence phenomenon.Its preparation method: 1) prepare N ethyl carbazole with carbazole and dithyl sulfate for raw material；2) in the presence of phosphorus oxychloride, with N ethyl carbazole and N, N dimethylformamide is that raw material prepares solid N ethyl carbazole 3,6 dicarbaldehyde；3), in pyridine solvent, in the presence of nafoxidine, with N ethyl carbazole 3,6 dicarbaldehyde and 2 tectoquinones for raw material, target product is prepared.This product has preferable electronic transmission performance and excellent luminosity, has using value in field of photovoltaic materials.
Description
Technical field
The present invention relates to carbazole derivates prepare, particularly belong to a kind of 3,6-bis-(anthraquinone-2-vinyl)-N-ethyl carbazole
And preparation method thereof.
Background technology
Carbazole is enriched in the unsaturated fused heterocyclic compound of electronics, has the structure of similar conjugated alkene, has relatively good
Electronic transmission performance and excellent photoelectric property, be a very important chemical raw material of class.Carbazole compound is prone to carry out
Structural modification, can be readily incorporated into various functional group on carbazole ring.Carbazole derivates is some position at carbazole molecules
Introduce specific functional group thus obtain the compound with New function, utilize the photoelectric properties that carbazole is unique, design and
Synthesis organic conjugated compounds, wherein utilizes ICT (Intramolecular electron transfer) Process Design carbazole derivates more.These derivants
There is photoinduction transfer character, can be as organic molecule electronics functional material, such as photoelectric conversion material, nonlinear optical organic
The fields such as material, optoelectronic information storage material, fluorescent probe, biomolecule identification and labelling enjoy the favor of researchers.
Summary of the invention:
It is an object of the invention to provide a kind of A-π-D-π-A electric charge in molecule transfer type, there is the change of double fluorescence phenomenon
Compound 3,6-bis-(anthraquinone-2-vinyl)-N-ethyl carbazole and preparation method thereof.
The one 3 that the present invention provides, 6-bis-(anthraquinone-2-vinyl)-N-ethyl carbazole, its structural formula:
The one 3 that the present invention provides, the preparation method of 6-bis-(anthraquinone-2-vinyl)-N-ethyl carbazole, including walking as follows
Rapid:
1) carbazole is dissolved in acetone, stir at 40 DEG C to fully dissolving, when solution becomes colorless transparence, slowly
Adding dithyl sulfate, solution becomes faint yellow, when solution becomes golden yellow, and stopped reaction, naturally cool to room temperature, then to
Solution adds sodium hydrate aqueous solution, after stirring 25～30min, sucking filtration, is dried, dehydrated alcohol recrystallization, obtains N-ethyl
Carbazole, reaction equation is as follows:
2), phosphorus oxychloride is slowly added in the N,N-dimethylformamide solution using anhydrous magnesium sulfate dried；Again will
N-ethyl carbazole is dissolved in the DMF solution using anhydrous magnesium sulfate dried, they is mixed, and stirs 30
～32h, stopped reaction, it is cooled to room temperature；Being poured into water by solution after cooling and be stirred vigorously 2～3h, the amount of described water is molten
Long-pending 5-10 times of liquid；Add sodium hydrate aqueous solution, regulate PH to 7.8-8.2 with sodium bicarbonate, extract with dichloromethane, have
Machine anhydrous sodium sulfate is dried, and adds proper silica gel, is spin-dried for, and pillar layer separation purifies, and obtains solid N-ethyl carbazole-3,6-
Dicarbaldehyde, reaction equation is as follows:
3), 2-methylanthraquinone is dissolved in pyridine, heats and stir；N-ethyl carbazole-3,6-dicarbaldehyde is dissolved in
In pyridine, stirring makes it fully dissolve, and is then added drop-wise in above-mentioned 2-methylanthraquinone solution, adds nafoxidine, 90～92
DEG C condensing reflux 38～40h, adds appropriate anhydrous sodium sulfate, stands, and is removed by supernatant, adds proper silica gel, is spin-dried for, post color
Spectrum separating-purifying, obtains solid 3,6-bis-(anthraquinone-2-vinyl)-N ethyl carbazole, and reaction equation is as follows:
Wherein: in step (1), carbazole is 1:1.88～3 with the mass ratio of dithyl sulfate；The concentration of sodium hydroxide is
50%～60%；
In step (2), the volume ratio of phosphorus oxychloride, DMF and N-ethyl carbazole is 1～1.5:1:0.4
～0.5, wherein the concentration of N-ethyl carbazole is 3.2mol/L；The mass ratio of N-ethyl carbazole and sodium hydroxide solution be 1:6～
6.5；The concentration of sodium hydroxide solution is 3mol/L；Column chromatography developing solvent: V (dichloromethane): V (ethyl acetate)=20～22:
1；
In step (3), 2-methylanthraquinone and N-ethyl carbazole-3, the mass ratio of 6-dicarbaldehyde is 9～12:5；Column chromatography exhibition
Open agent V (petroleum ether): V (ethyl acetate)=1:3～4.
The 3 of present invention synthesis, 6-bis-(anthraquinone-2-vinyl)-N-Ethyl carbazole compounds, there is preferable electric transmission
Performance and excellent luminosity, study its luminescent behavior, finds that its luminescent behavior depends strongly on the polarity of solvent, and with molten
The increase of agent polarity, there is obvious red shift in its fluorescence maximum emission peak, Intramolecular electron transfer (ICT) occurs and highly polar
Occurring in that double fluorescence phenomenon in solvent acetonitrile, this compound has potential using value in field of photovoltaic materials.
Accompanying drawing explanation
Fig. 1 is 3,6-bis-(anthraquinone-2-vinyl)-N-ethyl carbazole normalization fluorescence spectrum in different solvents
Fig. 2 is the maximum excitation of dipole polarization rate Δ f and compound and launches wave-number difference relation curve
Fig. 3 is 3, electric charge transfer schematic diagram in the planar molecule of 6-bis-(anthraquinone-2-vinyl)-N-ethyl carbazole
Detailed description of the invention
Embodiment 1
1) adding 10g carbazole and 120ml acetone in the there-necked flask of 250ml, frame is in the intelligence with mechanical stirring device
On energy temperature control magnetic stirring apparatus, stir at 40 DEG C to fully dissolving, when solution becomes colorless transparence, slowly add in flask
Entering 16ml (about 18.8g) dithyl sulfate, solution becomes faint yellow, after reaction 20min, when solution i.e. becomes golden yellow, closes
Temperature control and stirring switch, after solution naturally cools to room temperature, adding 5.45ml concentration in solution with constant pressure funnel is
The sodium hydroxide solution of 54.5%, opens stirring switch, and arranging rotating speed is 800r/min, stops stirring, by it after reaction 20min
Pour in the beaker equipped with about 700ml water, stand, have a large amount of rice white flocculent substance to separate out, sucking filtration successively, it is dried, with anhydrous
Ethyl alcohol recrystallization, obtains the needle crystals 18.1g of white, and productivity is 76.3%, and fusing point is 72-74 DEG C.1HNMR (300MHz,
CDCl3), δ: 8.1～7.1 (7H, Ar-H)；4,3～4.2 (2H ,-CH2)；1.4～1.3 (3H ,-CH3)。
2) in the round-bottomed flask of 150ml, add the 19mlN.N-dimethylformamide that anhydrous magnesium sulfate is dried, be placed in
On ice-water bath, 25ml phosphorus oxychloride being slowly added in flask with constant pressure funnel, completely, solution gradually becomes in 15min dropping
For Chinese red；Again 5.0gN-ethyl carbazole is dissolved in the DMF that 8ml anhydrous magnesium sulfate is dried, slow
Slowly it is added drop-wise in round-bottomed flask.Flask is transferred on temperature control magnetic stirring apparatus, and design temperature is 100 DEG C, anti-in course of reaction
Answer thing color to gradually become bronzing and gradually become blackish green still later, stop heating and stirring after 30h, be cooled to room temperature.Will
Blackish green solution is poured in the beaker equipped with 250ml water and is stirred vigorously about 2h, is slowly added to the hydroxide that 30g concentration is 3mol/L
Sodium water solution, then regulate PH to 8 with sodium bicarbonate, extracting with 400ml dichloromethane, extract distilled water is washed till clarification, has
Machine anhydrous sodium sulfate is dried, and 200-300 is than purpose proper silica gel in addition, is spin-dried for, and pillar layer separation purifies (developing solvent: V bis-Chloromethanes: VEthyl acetate=20:1), obtain yellow powdery solid 3.2g, productivity is 49.7%, and fusing point is 168-170 DEG C.1HNMR
(300MHz, CDCl3), δ: 10.0 (H ,-CHO)；8.5～7.1 (7H, carbazoles)；4.3 (2H ,-CH2)；1.4～1.6 (3H ,-
CH3)。
3) 2-methylanthraquinone 0.9g and 25ml pyridine are added in there-necked flask, on frame to electric jacket, open stirring switch.
15ml pyridine joins 0.5gN-ethyl carbazole-3, and in 6-dicarbaldehyde, stirring makes it fully dissolve, and transfers to the constant voltage of 20ml
In Dropping funnel, Dropping funnel is contained on there-necked flask, controls speed, drip off half an hour, add 1ml nafoxidine, remove
Removing Dropping funnel, add condensing reflux pipe, 90 DEG C of condensing refluxes, solution gradually has yellow to become light red to eventually become brown,
After reaction 38h, in flask, add appropriate anhydrous sodium sulfate, stand, supernatant is transferred in 150ml single port flask, add
Proper silica gel, is spin-dried for, and pillar layer separation purifies (developing solvent: VPetroleum ether: VEthyl acetate=1:3), obtain red-brown powder shape solid
0.39g, productivity is 32.4%, and fusing point is 188-190 DEG C.1HNMR (300MHz, CDCl3), δ: 6.858 (2H ,-CH=CH-)；
8.6～7.26 (14H, carbazole and anthraquinones)；4.4 (2H ,-CH2)；1.41～1.38 (3H ,-CH3)。
Fig. 1 for for 3,6-bis-(anthraquinone-2-vinyl)-N-ethyl carbazole normalization fluorescence spectrum in different solvents,
In figure: solvent: 1, hexamethylene；2, benzene；3, ethyl acetate；4, dichloromethane, 5, acetonitrile.Along with the increase of solvent polarity, fluorescence
The maximum emission peak of spectrum has had certain red shift, and occurs in that two fluorescent belts in intensive polar solvent acetonitrile, the most double glimmering
Optical phenomenon.
Fig. 2 is the maximum excitation of dipole polarization rate Δ f and compound and launches wave-number difference relation curve, with the orientation of solvent
Polarizability (mapped by Δ f), has obtained compound Lippert-in 5 kinds of different solvents by stoke (Stokes) displacement
The curve of Mataga.In figure: 1, hexamethylene,；2, benzene；3, ethyl acetate；4, dichloromethane；5, acetonitrile.In ethyl acetate
Lippert-Mataga equation departs from linear, thus it is speculated that 3,6-bis-(anthraquinone-2-vinyl)-N-ethyl carbazole may be with ethyl acetate
There is intermolecular charge transfer so that the emission spectrum of compound complicates.Oblique according to Lippert-Mataga equation straight line
Rate, can calculate the dipole moment (Δ μ) between excited state and ground state:
According to minimum energy principle, a diameter of 1.25nm of the molecule of optimized mistake.Can be estimated by the slope of curve in figure
The dipole difference calculating compound is 3.014D, it can be said that bright under light excites, 3,6-bis-(anthraquinone-2-vinyl)-N-second
Base carbazole there occurs Intramolecular electron transfer.
Fig. 3 is 3, electric charge transfer schematic diagram, N-second in the planar molecule of 6-bis-(anthraquinone-2-vinyl)-N-ethyl carbazole
Base carbazole has strong electron donation, and anthraquinone has strong electron-withdrawing power, and electric charge can be transferred to two ends from carbazole group
Anthraquinone radicals.
Claims (9)
1. one kind 3,6-bis-(anthraquinone-2-vinyl)-N-ethyl carbazole, it is characterised in that structural formula is:
2. one 3 as claimed in claim 1, the preparation method of 6-bis-(anthraquinone-2-vinyl)-N-ethyl carbazole, its feature
It is, comprises the steps:
1) carbazole is dissolved in acetone, stir at 40 DEG C to fully dissolving, when solution becomes colorless transparence, be slowly added to
Dithyl sulfate, solution becomes faint yellow, when solution becomes golden yellow, stopped reaction, naturally cool to room temperature, then to solution
Middle addition sodium hydrate aqueous solution, after stirring 25～30min, sucking filtration, it is dried, dehydrated alcohol recrystallization, obtains N-ethyl carbazole；
2) phosphorus oxychloride is slowly added in the N,N-dimethylformamide solution using anhydrous magnesium sulfate dried；Again by N-ethyl
Carbazole is dissolved in the DMF solution using anhydrous magnesium sulfate dried, they is mixed, and stirs 30～32h,
Stopped reaction, is cooled to room temperature；Being poured into water by solution after cooling and be stirred vigorously 2～3h, the amount of described water is liquor capacity
5-10 times；Adding sodium hydrate aqueous solution, regulate PH to 7.8-8.2 with sodium bicarbonate, extract with dichloromethane, organic facies is used
Anhydrous sodium sulfate is dried, and adds proper silica gel, is spin-dried for, and pillar layer separation purifies, and obtains solid N-ethyl carbazole-3,6-diformazan
Aldehyde；
3) 2-methylanthraquinone is dissolved in pyridine, heats and stir；N-ethyl carbazole-3,6-dicarbaldehyde is dissolved in pyridine
In, stirring makes it fully dissolve, and is then added drop-wise in above-mentioned 2-methylanthraquinone solution, adds nafoxidine, and 90～92 DEG C are cold
Solidifying backflow 38～40h, adds appropriate anhydrous sodium sulfate, stands, and is removed by supernatant, adds proper silica gel, is spin-dried for, and column chromatography is divided
From purification, obtain solid 3,6-bis-(anthraquinone-2-vinyl)-N ethyl carbazole.
The preparation method of the most as claimed in claim 23,6-bis-(anthraquinone-2-vinyl)-N-ethyl carbazole, it is characterised in that
In described step (1), carbazole is 1:1.88～3 with the mass ratio of dithyl sulfate.
The preparation method of the most as claimed in claim 23,6-bis-(anthraquinone-2-vinyl)-N-ethyl carbazole, it is characterised in that
In described step (1), the concentration of sodium hydroxide is 25～37.5mol/L.
The preparation method of the most as claimed in claim 23,6-bis-(anthraquinone-2-vinyl)-N-ethyl carbazole, it is characterised in that
In described step (2) volume ratio of phosphorus oxychloride, N,N-dimethylformamide and N-ethyl carbazole be 1～1.5:1:0.4～
0.5；Wherein the concentration of N-ethyl carbazole is 3.2mol/L.
The preparation method of the most as claimed in claim 23,6-bis-(anthraquinone-2-vinyl)-N-ethyl carbazole, it is characterised in that
In described step (2), N-ethyl carbazole is 1:6～6.5 with the mass ratio of sodium hydroxide solution, the concentration of sodium hydroxide solution
For 3mol/L.
The preparation method of the most as claimed in claim 23,6-bis-(anthraquinone-2-vinyl)-N-ethyl carbazole, it is characterised in that
The developing solvent of column chromatography in described step (2): V (dichloromethane): V (ethyl acetate)=20～22:1.
The preparation method of the most as claimed in claim 23,6-bis-(anthraquinone-2-vinyl)-N-ethyl carbazole, it is characterised in that
In described step (3), the mass ratio of 2-methylanthraquinone and N-ethyl carbazole-3,6-dicarbaldehyde is 9～12:5.
The preparation method of the most as claimed in claim 23,6-bis-(anthraquinone-2-vinyl)-N-ethyl carbazole, it is characterised in that
Developing solvent V (petroleum ether): V (the ethyl acetate)=1:3～4 of column chromatography in described step (3).
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Cited By (4)
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| CN106800525A (en) * | 2016-12-14 | 2017-06-06 | 中节能万润股份有限公司 | A kind of fluorenyl Anthraquinones electroluminescent organic material and its preparation method and application |
| CN107502341A (en) * | 2017-08-11 | 2017-12-22 | 江苏第二师范学院 | Piezoluminescence material crystals and preparation method and application |
| CN110183466A (en) * | 2019-07-19 | 2019-08-30 | 华东理工大学 | A kind of two pyrroles's alkene of condensed ring and its synthetic method |
| CN115991858A (en) * | 2023-03-23 | 2023-04-21 | 山东宇世巨化工有限公司 | Preparation method of high-temperature-resistant phenolic resin gel material |
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Cited By (7)
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| CN106800525A (en) * | 2016-12-14 | 2017-06-06 | 中节能万润股份有限公司 | A kind of fluorenyl Anthraquinones electroluminescent organic material and its preparation method and application |
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| CN107502341A (en) * | 2017-08-11 | 2017-12-22 | 江苏第二师范学院 | Piezoluminescence material crystals and preparation method and application |
| CN107502341B (en) * | 2017-08-11 | 2019-10-18 | 江苏第二师范学院 | Piezoluminescence material crystals and preparation method and application |
| CN110183466A (en) * | 2019-07-19 | 2019-08-30 | 华东理工大学 | A kind of two pyrroles's alkene of condensed ring and its synthetic method |
| CN110183466B (en) * | 2019-07-19 | 2022-02-18 | 华东理工大学 | Fused ring dipyrromethene and synthetic method thereof |
| CN115991858A (en) * | 2023-03-23 | 2023-04-21 | 山东宇世巨化工有限公司 | Preparation method of high-temperature-resistant phenolic resin gel material |
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Application publication date: 20161109 |