CN110272442A - One kind is containing double boron polycyclic aromatic hydrocarbons (PAH) fluorescent materials, preparation method and applications - Google Patents
One kind is containing double boron polycyclic aromatic hydrocarbons (PAH) fluorescent materials, preparation method and applications Download PDFInfo
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- CN110272442A CN110272442A CN201910649278.4A CN201910649278A CN110272442A CN 110272442 A CN110272442 A CN 110272442A CN 201910649278 A CN201910649278 A CN 201910649278A CN 110272442 A CN110272442 A CN 110272442A
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- boron
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
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- C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
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- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Abstract
The present invention discloses a kind of preparation method containing double boron polycyclic aromatic hydrocarbons (PAH) fluorescent materials; comprising steps of 1) under nitrogen protection; by 2; 2'- bis- (trimethyl silicane) base -1; bis- dinaphthalene of 1'- and anhydrous ferric trichloride add to reaction in Boron tribromide, remove unreacted Boron tribromide after reaction under reduced pressure；2) under nitrogen protection, mesitylene Grignard Reagent tetrahydrofuran solution is added dropwise, room temperature reaction has fluorescence-causing substance generation, after reaction, is concentrated, chromatographs to obtain orange red solid.The present invention is based on Si-B exchanges, α hydrogen easily leave away cyclization organic reaction feature, select ferric trichloride as catalyst, what building was had excellent performance contains double boron polycyclic aromatic hydrocarbons (PAH) fluorescent materials, the material belongs to green emission type compound, dissolubility is fine, and fluorescence quantum yield is higher, has very big application value in OLED, photoelectric cell, two-photon absorbing material domain；In addition, preparing the simple operating conditions of fluorescent material use, high income.
Description
Technical field
The present invention relates to one kind containing double boron polycyclic aromatic hydrocarbons (PAH) fluorescent materials, preparation method and applications, belongs to fluorescent material
Synthesis field.
Background technique
The thermodynamic stability of boracic organic compound is the difficult point of research, and boracic organic compound is usual to water and air
Unstable, unstable in order to solve the problems, such as, a kind of method is and hetero atom (P/N/O etc.) bonding increases stability；Other one
Kind method, is to make its stabilization by the way of increasing steric hindrance.Boracic polycyclic aromatic hydrocarbons (PAH) organic compound is the π of aromatic hydrocarbon
Conjugated system is formed with the P track of boron, there are good photoelectric properties, be widely used in two-photon absorbing material, OLED, photoelectricity
Battery etc..Existing boracic polycyclic aromatic hydrocarbons (PAH) organic compound fluorescent material, preparation process is more complex, low yield.
Summary of the invention
In view of the above existing problems in the prior art, the present invention provides one kind containing double boron polycyclic aromatic hydrocarbons (PAH) fluorescent materials, molten
Solution property very well (alkane solvents), external quantum efficiency (EQE) be 6%, compound Density function theory obtain HOMO be-
5.51 and LUMO is -2.26, is useful in field of photovoltaic materials.
There is provided the preparation method and application containing double boron polycyclic aromatic hydrocarbons (PAH) fluorescent materials for another object of the present invention.
To achieve the goals above, one kind that the present invention uses contains double boron polycyclic aromatic hydrocarbons (PAH) fluorescent materials, and structural formula is such as
Under:
Specific preparation method, comprising the following steps:
1) 2,2'- bis- (trimethyl silicane) base -1,1'-, bis- dinaphthalene and anhydrous ferric trichloride under nitrogen protection, are added to three
Reaction, removes unreacted Boron tribromide in boron bromide under reduced pressure after reaction；
2) under nitrogen protection, mesitylene Grignard Reagent tetrahydrofuran solution is added dropwise, room temperature reaction has fluorescence-causing substance
It generates, after reaction, is concentrated, chromatographs to obtain Chinese red solid.
As an improvement, the molar ratio of 2,2'- bis- (trimethyl silicane) base -1,1'-, bis- dinaphthalene and Boron tribromide is 1:
0.01~0.1.
As an improvement, the molar ratio of 2,2'- bis- (trimethyl silicane) base -1,1'-, bis- dinaphthalene and anhydrous ferric trichloride is
1:0.05~0.1.
As an improvement, 2,2'- bis- (trimethyl silicane) base -1,1'-, bis- dinaphthalene and mesitylene Grignard Reagent are rubbed
You are than being 1:2.2~3.0；Mesitylene magnesium bromide i.e. 2,4,6- trimethylbenzene can be used in the mesitylene Grignard Reagent
Magnesium bromide (MesMgBr) can be easily obtained also by conventional general grignard reagent preparation method from profession
Reagent producer obtains.
As an improvement, reaction temperature is 50-60 DEG C in the step 1), the reaction time is 12~36h.
In addition, Chinese red solid obtained is waved in the system of n-hexane and methylene chloride in solvent under room temperature
The monocrystalline containing double boron polycyclic aromatic hydrocarbons (PAH) fluorescent materials is obtained after hair.
Finally, additionally providing the application containing double boron polycyclic aromatic hydrocarbons (PAH) fluorescent materials in photoelectric material.
As an improvement, described be used for two-photon absorbing material, OLED, photoelectric cell containing double boron polycyclic aromatic hydrocarbons (PAH) fluorescent materials
Any one of.
Compared with prior art, the present invention is based on Si-B exchange, α hydrogen easily leave away cyclization organic reaction feature, select three
For iron chloride as catalyst, ferric trichloride is lewis acid, and from the point of view of the mechanism of reaction, which reduce the energy of transition state, is made
The fracture of C-Si key, C-B key generate, and contain double boron polycyclic aromatic hydrocarbons (PAH) fluorescent materials with what building was had excellent performance, and in the polycyclic virtue of double boron
Since its biggish pi-conjugated system of P- keeps its structure more stable in fragrant hydrocarbon, while in common solvent such as methylene chloride, n-hexane
And the dissolubility in other alkane solvents is fine.Fluorescent material produced by the present invention belongs to green emission type compound, glimmering
Quantum yield is higher, has very big application value in OLED, photoelectric cell, two-photon absorbing material domain；In addition, of the invention
Prepare simple operating conditions, the high income of the use of green fluorescence material.
Detailed description of the invention
Fig. 1 is the obtained fluorescent emission containing double boron polycyclic aromatic hydrocarbons (PAH) fluorescent materials in methylene chloride of the embodiment of the present invention 1
Spectrogram；
Fig. 2 is that the hydrogen nuclear magnetic resonance spectrogram containing double boron polycyclic aromatic hydrocarbons (PAH) fluorescent materials is made in the embodiment of the present invention 1；
Fig. 3 is that the X-ray single crystal diffraction map containing double boron polycyclic aromatic hydrocarbons (PAH) fluorescent materials is made in the embodiment of the present invention 1.
Specific embodiment
Following embodiments are further explanations for the content of present invention using as the explaination to the technology of the present invention content, but
Substantive content of the invention is not limited in described in following embodiments, those skilled in the art can with and should know appoint
What simple change or replacement based on true spirit should belong to protection scope of the presently claimed invention.
Embodiment 1
A kind of preparation method containing double boron polycyclic aromatic hydrocarbons (PAH) fluorescent materials, comprising the following steps:
1) by two dinaphthalene 500mg (1.25mmol) of (trimethyl silicane) base of 2,2'- bis- -1,1'- and anhydrous ferric trichloride
20.28mg (0.125mmol) is added in reaction flask, replaces nitrogen, and Boron tribromide 5ml is added, and (Boron tribromide is both reactant
It is solvent, can guarantee that raw material sufficiently dissolves, Boron tribromide excessively will increase insecurity in post-processing too much), at 60 DEG C
It is kept stirring reaction 36h, unreacted Boron tribromide is removed under the conditions of conventional vacuum；
2) mesitylene Grignard Reagent tetrahydrofuran solution 10ml slowly under nitrogen protection, is added dropwise and (contains 3.75mmol
Grignard reagent), 10min is reacted at room temperature, has the new product of fluorescence to generate, reaction terminates, and the system is concentrated, silica gel column chromatography is (just
Hexane), obtain the Chinese red solid of 268.4mg, yield 42%.In addition, can be by Chinese red solid obtained in n-hexane and two
In the system of chloromethanes, the monocrystalline containing double boron polycyclic aromatic hydrocarbons (PAH) fluorescent materials is obtained after solvent flashing under room temperature.
The synthetic route containing double boron polycyclic aromatic hydrocarbons (PAH) fluorescent materials is as follows:
In addition, above-mentioned fluorescence emission spectrogram of compound, hydrogen nuclear magnetic resonance spectrogram and X- containing double boron polycyclic aromatic hydrocarbons (PAH) fluorescent materials
Ray single crystal diffraction map is distinguished；
Wherein, 1HNMR (400MHz, CDCl3), δ [ppm]: 8.17 (dd, J=8Hz, 1.2Hz, 2H), 8.11 (dd, J=
6.8Hz, 1.6Hz, 2H), 7.95 (q, J=23.2Hz, 4H), 6.64 (dd, J=7.6Hz, 6.8Hz, 2H), 7.03 (s, 4H),
2.48(s,6H),2.11(s,12H)。
Embodiment 2
A kind of preparation method containing double boron polycyclic aromatic hydrocarbons (PAH) fluorescent materials, comprising the following steps:
1) by two dinaphthalene 500mg (1.25mmol) of (trimethyl silicane) base of 2,2'- bis- -1,1'- and anhydrous ferric trichloride
2.028mg (0.0125mmol) is added in reaction flask, replaces nitrogen, and Boron tribromide 5ml is added, reaction is kept stirring at 60 DEG C
36h removes unreacted Boron tribromide at reduced pressure conditions；
2) mesitylene Grignard Reagent tetrahydrofuran solution 10ml (3.75mmol) slowly is added dropwise under nitrogen protection, room
Temperature reaction 10min, has the new product of fluorescence to generate, and reaction terminates, and the system is concentrated, silica gel column chromatography (n-hexane) obtains
The Chinese red solid of 185.3mg, yield 29%.
Wherein, nuclear magnetic resonance spectroscopy are as follows: 1HNMR (400MHz, CDCl3), δ [ppm]: 8.17 (dd, J=8Hz,
1.2Hz, 2H), 8.11 (dd, J=6.8Hz, 1.6Hz, 2H), 7.95 (q, J=23.2Hz, 4H), 6.64 (dd, J=7.6Hz,
6.8Hz,2H),7.03(s,4H),2.48(s,6H),2.11(s,12H)。
Embodiment 3
A kind of preparation method containing double boron polycyclic aromatic hydrocarbons (PAH) fluorescent materials, comprising the following steps:
1) by two dinaphthalene 500mg (1.25mmol) of (trimethyl silicane) base of 2,2'- bis- -1,1'- and anhydrous ferric trichloride
20.28mg (0.125mmol) is added in reaction flask, replaces nitrogen, and Boron tribromide 5ml is added, reaction is kept stirring at 50 DEG C
36h removes unreacted Boron tribromide at reduced pressure conditions；
2) mesitylene Grignard Reagent tetrahydrofuran solution 10ml (3.75mmol) slowly is added dropwise under nitrogen protection, room
Temperature reaction 10min, has the new product of fluorescence to generate, and reaction terminates, and the system is concentrated, silica gel column chromatography (n-hexane) obtains
The Exocarpium Citri Rubrum solid of 244.1mg, yield 38.2%.
Its nuclear magnetic resonance spectroscopy are as follows: 1HNMR (400MHz, CDCl3), δ [ppm]: 8.17 (dd, J=8Hz, 1.2Hz, 2H),
8.11 (dd, J=6.8Hz, 1.6Hz, 2H), 7.95 (q, J=23.2Hz, 4H), 6.64 (dd, J=7.6Hz, 6.8Hz, 2H),
7.03(s,4H),2.48(s,6H),2.11(s,12H)。
Embodiment 4
A kind of preparation method containing double boron polycyclic aromatic hydrocarbons (PAH) fluorescent materials, comprising the following steps:
1) by two dinaphthalene 500mg (1.25mmol) of (trimethyl silicane) base of 2,2'- bis- -1,1'- and anhydrous ferric trichloride
20.28mg (0.125mmol) is added in reaction flask, replaces nitrogen, and Boron tribromide 5ml is added, reaction is kept stirring at 50 DEG C
For 24 hours, unreacted Boron tribromide is removed at reduced pressure conditions；
2) mesitylene Grignard Reagent tetrahydrofuran solution 10ml (3.75mmol) slowly is added dropwise under nitrogen protection, room
Temperature reaction 10min, has the new product of fluorescence to generate, and reaction terminates, and the system is concentrated, silica gel column chromatography (n-hexane) obtains
The Chinese red solid of 249.3mg, yield 39%.
Its nuclear magnetic resonance spectroscopy are as follows: 1HNMR (400MHz, CDCl3), δ [ppm]: 8.17 (dd, J=8Hz, 1.2Hz, 2H),
8.11 (dd, J=6.8Hz, 1.6Hz, 2H), 7.95 (q, J=23.2Hz, 4H), 6.64 (dd, J=7.6Hz, 6.8Hz, 2H),
7.03(s,4H),2.48(s,6H),2.11(s,12H)。
Embodiment 5
A kind of preparation method containing double boron polycyclic aromatic hydrocarbons (PAH) fluorescent materials, comprising the following steps:
1) by two dinaphthalene 500mg (1.25mmol) of (trimethyl silicane) base of 2,2'- bis- -1,1'- and anhydrous ferric trichloride
20.28mg (0.125mmol) is added in reaction flask, replaces nitrogen, and Boron tribromide 5ml is added, reaction is kept stirring at 50 DEG C
For 24 hours, unreacted Boron tribromide is removed at reduced pressure conditions；
2) mesitylene Grignard Reagent tetrahydrofuran solution 10ml (2.75mmol) slowly under nitrogen protection, is added dropwise,
10min is reacted at room temperature, has the new product of fluorescence to generate, reaction terminates, and the system is concentrated, silica gel column chromatography (n-hexane) obtains
The Chinese red solid of 179.0mg, yield 28%.
Its nuclear magnetic resonance spectroscopy are as follows: 1HNMR (400MHz, CDCl3), δ [ppm]: 8.17 (dd, J=8Hz, 1.2Hz, 2H),
8.11 (dd, J=6.8Hz, 1.6Hz, 2H), 7.95 (q, J=23.2Hz, 4H), 6.64 (dd, J=7.6Hz, 6.8Hz, 2H),
7.03(s,4H),2.48(s,6H),2.11(s,12H)。
Embodiment 6
A kind of preparation method containing double boron polycyclic aromatic hydrocarbons (PAH) fluorescent materials, comprising the following steps:
1) by two dinaphthalene 500mg (1.25mmol) of (trimethyl silicane) base of 2,2'- bis- -1,1'- and anhydrous ferric trichloride
10.14mg (0.0625mmol) is added in reaction flask, replaces nitrogen, and Boron tribromide 5ml is added, reaction is kept stirring at 60 DEG C
For 24 hours, unreacted Boron tribromide is removed at reduced pressure conditions；
2) mesitylene Grignard Reagent tetrahydrofuran solution 10ml (2.75mmol) slowly under nitrogen protection, is added dropwise,
10min is reacted at room temperature, has the new product of fluorescence to generate, reaction terminates, and the system is concentrated, silica gel column chromatography (n-hexane) obtains
The tangerine Exocarpium Citri Rubrum solid of 159.8mg, yield 25%.
Its nuclear magnetic resonance spectroscopy are as follows: 1HNMR (400MHz, CDCl3), δ [ppm]: 8.17 (dd, J=8Hz, 1.2Hz, 2H),
8.11 (dd, J=6.8Hz, 1.6Hz, 2H), 7.95 (q, J=23.2Hz, 4H), 6.64 (dd, J=7.6Hz, 6.8Hz, 2H),
7.03(s,4H),2.48(s,6H),2.11(s,12H)。
The present invention is made containing double boron polycyclic aromatic hydrocarbons (PAH) fluorescent materials, and double boron are embedded in the structure of polycyclic aromatic hydrocarbons (PAH), preparation side
Method synthesis yield is higher, and synthesis step is short, easy to operate, and obtained material belongs to small molecule emitter material, and dissolubility is preferable,
Quantum efficiency is high, light emitting device field with good application prospect.
The foregoing is merely illustrative of the preferred embodiments of the present invention, is not intended to limit the invention, all in essence of the invention
Made any modification, equivalent replacement or improvement etc., should all be included in the protection scope of the present invention within mind and principle.
Claims (9)
1. one kind is containing double boron polycyclic aromatic hydrocarbons (PAH) fluorescent materials, which is characterized in that its structural formula is as follows:
2. the preparation method containing double boron polycyclic aromatic hydrocarbons (PAH) fluorescent materials described in a kind of claim 1, which is characterized in that including following
Step:
1) 2,2'- bis- (trimethyl silicane) base -1,1'-, bis- dinaphthalene and anhydrous ferric trichloride under nitrogen protection, are added into tribromide
Reaction, removes unreacted Boron tribromide in boron under reduced pressure after reaction；
2) under nitrogen protection, mesitylene Grignard Reagent tetrahydrofuran solution is added dropwise, room temperature reaction has fluorescence-causing substance production
It is raw, after reaction, it is concentrated, chromatographs to obtain Chinese red solid.
3. the preparation method according to claim 2 containing double boron polycyclic aromatic hydrocarbons (PAH) fluorescent materials, which is characterized in that described 2,
The molar ratio of two dinaphthalene of (trimethyl silicane) base of 2'- bis- -1,1'- and Boron tribromide is 1:0.01~0.1.
4. the preparation method according to claim 2 containing double boron polycyclic aromatic hydrocarbons (PAH) fluorescent materials, which is characterized in that described 2,
The molar ratio of two dinaphthalene of (trimethyl silicane) base of 2'- bis- -1,1'- and anhydrous ferric trichloride is 1:0.05~0.1.
5. the preparation method according to claim 2 containing double boron polycyclic aromatic hydrocarbons (PAH) fluorescent materials, which is characterized in that described 2,
The molar ratio of two dinaphthalene of (trimethyl silicane) base of 2'- bis- -1,1'- and mesitylene Grignard Reagent is 1:2.2~3.0.
6. the preparation method according to claim 2 containing double boron polycyclic aromatic hydrocarbons (PAH) fluorescent materials, which is characterized in that the step
It is rapid 1) in reaction temperature be 50-60 DEG C, the reaction time be 12~36h.
7. the preparation method according to claim 2 containing double boron polycyclic aromatic hydrocarbons (PAH) fluorescent materials, which is characterized in that will be made
Chinese red solid in the system of n-hexane and methylene chloride, obtained after solvent flashing under room temperature containing double polycyclic virtues of boron
The monocrystalline of fragrant hydrocarbon fluorescent material.
8. containing double any one of boron polycyclic aromatic hydrocarbons (PAH) fluorescent material and claim 2-7 preparation sides described in a kind of claim 1
The application containing double boron polycyclic aromatic hydrocarbons (PAH) fluorescent materials in photoelectric material is made in method.
9. application according to claim 8, which is characterized in that described to be used for double light containing double boron polycyclic aromatic hydrocarbons (PAH) fluorescent materials
Any one of sub- absorbing material, OLED, photoelectric cell.
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| CN112480155A (en) * | 2020-12-04 | 2021-03-12 | 吉林大学 | Thermal activation delayed fluorescence material containing double-boron polycyclic aromatic hydrocarbon and organic electroluminescent device using thermal activation delayed fluorescence material as light emitting layer |
| CN114685549A (en) * | 2022-04-25 | 2022-07-01 | 南开大学 | Preparation method of novel four-coordination bisboranofluorene fluorescent compound |
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| CN114685549A (en) * | 2022-04-25 | 2022-07-01 | 南开大学 | Preparation method of novel four-coordination bisboranofluorene fluorescent compound |
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Application publication date: 20190924 |