CN110437254A - The asymmetric non-fullerene small molecule receptor material of one kind and its application - Google Patents
The asymmetric non-fullerene small molecule receptor material of one kind and its application Download PDFInfo
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- CN110437254A CN110437254A CN201910796641.5A CN201910796641A CN110437254A CN 110437254 A CN110437254 A CN 110437254A CN 201910796641 A CN201910796641 A CN 201910796641A CN 110437254 A CN110437254 A CN 110437254A
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains four or more hetero rings
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H—ELECTRICITY
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- 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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- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Abstract
The present invention provides the asymmetric non-fullerene small molecule receptor material of one kind and its application, belongs to organic compound synthesis and organic solar batteries device preparation technical field.Asymmetric non-fullerene small molecule receptor material provided by the invention, which compensates for symmetrical non-fullerene small molecule receptor, has the shortcomings that weaker molecule combines energy and lesser molecular dipole moment, be conducive to enhance intermolecular interaction, possess excellent light absorption and carrier transmission performance, higher short circuit current and energy conversion efficiency can be achieved in organic solar batteries.It is with good dissolubility simultaneously, it is soluble in common organic solvents, electron mobility with higher, it is used to prepare the organic solar batteries of high short circuit current and high-energy conversion efficiency, show that it is a kind of acceptor material with excellent performance, there is huge potential using value in photoelectric field, at the same the present invention to using asymmetric non-fullerene acceptor strategy provide deeper into understanding.
Description
Technical field
The invention belongs to organic compound synthesis and organic solar batteries device preparation technical fields, and in particular to a kind of
Asymmetric non-fullerene small molecule receptor material and its application.
Background technique
Disclosing the information of the background technology part, it is only intended to increase understanding of the overall background of the invention, without certainty
It is considered as recognizing or implying in any form that information composition has become existing skill well known to persons skilled in the art
Art.
In recent years, in face of the energy crisis of growing tension, the ecological environment constantly deteriorated, development green, sustainable development
New energy become the important selection of the mankind.The earth can create generation with only the 1/2200000000 of solar radiation energy
Boundary's all things on earth, therefore develop and use solar energy and be undoubtedly excellent energy approach.And solar battery is to convert light into for electric current, is
A kind of photoelectric conversion.The scientist of AT&T Labs, the U.S. in 1954 prepares practical inorganic solar cell, is mankind's benefit
The milestone of electric energy is converted directly into solar energy.Then, this technology is fast-developing and spreads.But this kind of battery is deposited
Cost is high, processing complexity, the defect outstanding such as operation cost height, it is limited in the application of numerous areas.Therefore, it seeks
New solar cell material is looked for, has seemed very urgent.
Recently, there is weight by the body heterojunction organic solar batteries that conjugated polymer donor and small molecule receptor form
Measure it is light, translucent, can large area printing processing, low cost the advantages that and attract attention, be the important hair of next-generation photovoltaic technology
Open up target.Currently based on classic receptor material fullerene (PC61BM and PC71BM) optimal performance of battery alreadys exceed 11%.Though
Right this kind of acceptor material no doubt has many advantages, such as that very high electron mobility, exciton fission speed are fast, but they are visible
The absorption of light and near infrared region is weak, energy level adjustable range is narrow, is easy aggregation leads to that device is unstable, expensive etc. many lacks
Point greatly hinders the further development of organic solar batteries.Therefore, non-fullerene acceptor becomes nearly research in 5 years
Hot spot.The type of non-fullerene acceptor material is abundant, controllability is strong, and can match with numerous donor materials and realize high-performance
Device efficiency.Compared with symmetrical non-fullerene small molecule receptor, asymmetric non-fullerene small molecule receptor has stronger point
Son combines the potential advantages such as energy and biggish molecular dipole moment, is conducive to enhance intermolecular interaction, improves electron mobility
With organic photovoltaic devices performance.
So far, the photoelectric conversion efficiency of the organic solar batteries based on asymmetric non-fullerene small molecule receptor is
Nearly 13% in 2018 has been stepped up from 1% in 2010.But inventors have found that currently based on asymmetric non-fullerene
The organic solar batteries efficiency of small molecule receptor be more than 13% combination it is seldom, efficiency is still in urgent need to be improved.
Summary of the invention
In view of the above shortcomings of the prior art, the present invention provide it is a kind of condensed based on thiophene and pyrroles it is polycyclic asymmetric non-
Fullerene small molecule receptor material, mild condition simple by preparation, while the organic receptor being prepared may be used as
The receptor of organic solar batteries to greatly improve it in photoelectric field application range, therefore has good reality
Using value.
The present invention is achieved through the following technical solutions:
It is small to provide a kind of asymmetric non-fullerene of the heptatomic ring condensed based on thiophene and pyrroles for the first aspect of the invention
Numerator acceptor material, its core skeleton structural formula of the acceptor material have following any structure, and however, it is not limited to this:
Wherein, R1,R2,R4,R5It can be independently selected from hydrogen atom, alkyl or alkoxy.
The end group structural formula (shown in *) of above-mentioned core skeleton structural formula has following any structure, but does not limit to
In this:
Wherein, R3, R6Independently selected from hydrogen atom, alkyl, alkoxy or halogen；
X is selected from O, S, Se, the oxygen group elements such as Te.
The second aspect of the invention provides above-mentioned asymmetric non-fullerene small molecule receptor material as battery material
Using.
The third aspect of the invention provides a kind of organic solar batteries photoactive layer, the organic solar batteries
Photoactive layer includes above-mentioned asymmetric non-fullerene small molecule receptor material.
The fourth aspect of the invention, provides a kind of organic solar batteries, and the organic solar batteries include above-mentioned
Asymmetric non-fullerene small molecule receptor material and/or above-mentioned photoactive layer.
The fifth aspect of the invention, provides above-mentioned asymmetric non-fullerene small molecule receptor material and/or above-mentioned light is living
The application of property layer and/or organic solar batteries in photoelectric field.
Advantageous effects of the invention:
Asymmetric non-fullerene small molecule receptor material provided by the invention compensates for symmetrical non-fullerene small molecule receptor
Having the shortcomings that weaker molecule combines can be conducive to enhance intermolecular interaction, possess excellent with lesser molecular dipole moment
Higher short circuit current (J can be achieved in good light absorption and carrier transmission performance in organic solar batteriessc) and energy turn
Change efficiency (PCE).
In the present invention, the asymmetric non-fullerene small molecule receptor material has good dissolubility, is soluble in often
See organic solvent, electron mobility with higher is used to prepare organic sun of high short circuit current and high-energy conversion efficiency
Energy battery is a kind of acceptor material with excellent performance, has huge potential using value, while this hair in photoelectric field
It is bright for using asymmetric non-fullerene acceptor strategy provide deeper into understanding.
Detailed description of the invention
The Figure of description for constituting a part of the invention is used to provide further understanding of the present invention, and of the invention shows
Examples and descriptions thereof are used to explain the present invention for meaning property, does not constitute improper limitations of the present invention.
Fig. 1 is the hydrogen spectrogram of 1 Chinese style 1 of the embodiment of the present invention.
Fig. 2 is the hydrogen spectrogram of 1 Chinese style 2 of the embodiment of the present invention.
Fig. 3 is the hydrogen spectrogram of 1 Chinese style 3 of the embodiment of the present invention.
Fig. 4 is the hydrogen spectrogram of 1 Chinese style 4 of the embodiment of the present invention.
Fig. 5 is the hydrogen spectrogram of 1 Chinese style 5 of the embodiment of the present invention.
Fig. 6 is the hydrogen spectrogram of 1 Chinese style 6 of the embodiment of the present invention.
Fig. 7 is the hydrogen spectrogram of 1 Chinese style 7 of the embodiment of the present invention.
Fig. 8 is the hydrogen spectrogram of 2 Chinese style 8 of the embodiment of the present invention.
Fig. 9 is the hydrogen spectrogram of 3 Chinese style 9 of the embodiment of the present invention.
Figure 10 is the photoelectric current-light for the organic solar batteries device that isoacceptor is not prepared in the embodiment of the present invention 4
Voltage curve.
Figure 11 is the EQE spectrogram for the organic solar batteries device that isoacceptor is not prepared in the embodiment of the present invention 4.
Specific embodiment
It is noted that following detailed description is all illustrative, it is intended to provide further instruction to the present invention.Unless another
It indicates, all technical and scientific terms used herein has usual with general technical staff of the technical field of the invention
The identical meanings of understanding.
It should be noted that term used herein above is merely to describe specific embodiment, and be not intended to restricted root
According to exemplary embodiments of the present invention.As used herein, unless the context clearly indicates otherwise, otherwise singular
Also it is 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 their combination.It should be understood that protection model of the invention
It encloses and is not limited to following specific specific embodiments；It is also understood that term used in the embodiment of the present invention is to retouch
Specific specific embodiment is stated, rather than limiting the scope of protection of the present invention.
In conjunction with specific example, the present invention is further illustrated, and following instance is not right merely to the explanation present invention
Its content is defined.If the experiment actual conditions being not specified in embodiment, usually according to normal condition, or according to reagent public affairs
Take charge of recommended condition；Reagent as used in the following examples, consumptive material etc., are commercially available unless otherwise specified.
As previously mentioned, the photoelectric conversion efficiency of the organic solar batteries based on asymmetric non-fullerene small molecule receptor is still
It is to be improved.
In view of this, providing a kind of seven yuan condensed based on thiophene and pyrroles in the specific embodiment of the present invention
The asymmetric non-fullerene small molecule receptor material of ring, its core skeleton structural formula of the acceptor material have following any knot
Structure, however, it is not limited to this:
Wherein, R1,R2,R4,R5It can be independently selected from hydrogen atom, alkyl or alkoxy；
In still another embodiment of the invention, R1,R2,R4,R5Alkyl or C1~C22 independently selected from C1~C20
Alkoxy.
In still another embodiment of the invention, R1Selected from-C6H13, R2Selected from-C8H17。
In still another embodiment of the invention, the end group structural formula of above-mentioned core skeleton structural formula (shown in *)
With following any structure, but not limited to this:
Wherein, R3, R6Independently selected from hydrogen atom, alkyl, alkoxy or halogen；
The halogen includes F, Cl, Br, I (preferably Cl)；
X is selected from O, S, Se, the oxygen group elements such as Te.Asymmetric non-fullerene small molecule receptor material of the invention has good
Dissolubility, common organic solvents are soluble in, while possessing excellent light absorption and carrier transmission performance, in organic solar
Higher short circuit current (J can be achieved in batterysc) and energy conversion efficiency (PCE).
In still another embodiment of the invention, above-mentioned asymmetric non-fullerene small molecule receptor material is provided as electricity
The application of pond material.
In still another embodiment of the invention, the battery is organic solar batteries.
In still another embodiment of the invention, the application is specially organic solar active material；Further
The application is organic solar batteries photoactive layer material.
In still another embodiment of the invention, provide a kind of organic solar batteries photoactive layer, it is described it is organic too
Positive energy battery photoactive layer includes above-mentioned asymmetric non-fullerene small molecule receptor material.
In still another embodiment of the invention, the organic solar batteries photoactive layer further includes donor material,
The donor material is preferably PM6.
In still another embodiment of the invention, a kind of organic solar batteries, the organic solar batteries are provided
Including above-mentioned asymmetric non-fullerene small molecule receptor material and/or above-mentioned photoactive layer.
In still another embodiment of the invention, provide above-mentioned asymmetric non-fullerene small molecule receptor material and/or
The application of above-mentioned photoactive layer and/or organic solar batteries in photoelectric field.
Explanation is further explained to the present invention by the following examples, but is not construed as limiting the invention.It should be understood that
These examples are only for illustrating the present invention and are not intended to limit the scope of the present invention.
Embodiment 1
The synthesis of compound 1: under nitrogen protection, by the anhydrous tetrahydro furan of 3 bromo thiophene (15g, 92mmol)
The cooling of (150ml) solution is -78 DEG C, and LDA (58ml, 1.6M, 92mmol) then is added dropwise, is added dropwise within 30 minutes.Then -78
DEG C stirring 1 hour, anhydrous CuCl2 (14.9g, 110.4mmol) is added portionwise, after adding, continue stir 1 hour.Then
It is heated to room temperature and is stirred overnight, handled with the aqueous ammonium chloride solution of saturation, methylene chloride extraction, petroleum ether column obtains after chromatographing
10.9g white solid, yield 74%.
The synthesis of compound 2: under nitrogen protection, by compound 1 (1.35g, 4.2mmol), sodium tert-butoxide (0.95g,
10.18mmol), Pd (dba)3(0.1g, 1.09mmol), 1,1 '-dinaphthalene -2,2 '-bis- diphenylphosphines (0.26g, 0.42ml), nothing
Water-toluene (30ml) be added 100ml three-necked flask in, nitrogen be bubbled 10 minutes, then 2 ethyl hexylamine (0.56g, 0.71ml,
4.32mmol) be added.It is then refluxed for overnight, cold water quenching reaction, methylene chloride extraction being added, column chromatographs to obtain colorless oil
1.1g, yield 90%.
The synthesis of compound 3: under nitrogen protection, by thiophene (1.09g, 11.9mmol) and anhydrous tetrahydro furan (20ml)
It is added in there-necked flask, is cooled to 0 DEG C, n-BuLi (5.4ml, 2.2M, 11.9mmol) is added dropwise, and then stirs at such a temperature
1 hour.Then by the anhydrous ZnCl of preprepared2Anhydrous tetrahydro furan (20ml) solution of (0.8g, 0.6mmol) adds dropwise
Enter, then continues stirring 1 hour at such a temperature.Then by 2,5- dibromoterephthalic acid diethylester (4.5g, 11.9mmol)
It is added with Pd (PPh3) 4 (275mg, 0.238mmol).Heating is reacted to reflux, is kept for 6 hours, is then cooled to room temperature, water adds
Enter, methylene chloride extraction, sodium sulphate is dry, and petroleum ether: ethyl acetate crosses column chromatography, obtains colourless oil liquid 1.84g, produces
Rate 40.5%.
The synthesis of compound 4: under nitrogen protection, by compound 2 (2.07g, 7.1mmol) and anhydrous tetrahydro furan
(20ml) is added in there-necked flask, is cooled to -35 DEG C, n-BuLi (3.3ml, 2.2M, 7.1mmol) is added dropwise, then in the temperature
Degree lower stirring 0.5 hour.Then by the anhydrous ZnCl of preprepared2The anhydrous tetrahydro furan of (0.97g, 7.1mmol)
(20ml) solution is added dropwise, and then continues stirring 1 hour at such a temperature.Then compound 3 (2.2g, 5.8mmol) is added
Enter.Heating is reacted to reflux, is kept for 1 hour, is then cooled to room temperature, and water is added, and methylene chloride extraction, sodium sulphate is dry, stone
Oily ether: methylene chloride crosses column chromatography, obtains pale yellowish oil liquid 3.3g, yield 80%.
The synthesis of compound 5: under nitrogen protection, in there-necked flask by the bromo- 4- hexyl benzene of 1- (3.26g, 2.8ml,
It 13.5mmol) is dissolved in anhydrous tetrahydro furan (48ml), is cooled to -78 DEG C.N-BuLi (5.44ml, 2.5M, 7.1mmol) adds dropwise
Enter, then stirs 0.5 hour at such a temperature.Then by anhydrous the four of preprepared compound 4 (1.0g, 1.68mmol)
Hydrogen furans (10ml) solution is added dropwise, and then continues stirring 0.5 hour at such a temperature.It then is gradually warmed up room temperature, is stirred
It mixes overnight.TLC shows fully reacting, and reaction mixture is poured into water, and methylene chloride extraction, sodium sulphate is dry, is spin-dried for, and takes out true
Sky is dry.Without purifying, directly carry out in next step.
Crude product obtained by upper step is dissolved in glacial acetic acid (100ml), is stirred 5 minutes.Then the 2ml concentrated sulfuric acid is dissolved in 5ml ice
It is added dropwise in acetic acid, is then warming up to 120 DEG C and is refluxed overnight.It after TLC shows fully reacting, is poured into water, methylene chloride extraction
It takes, dilute sodium carbonate liquor washs organic phase, washing, anhydrous sodium sulfate drying.It is spin-dried for, petroleum ether: ethyl acetate (12:1) mistake
Column chromatography, obtains oily liquids 0.374g, yield 20%.
The synthesis of compound 6: under nitrogen protection, anhydrous DMF (5ml) is added in dry three-necked flask, is cooled to
POCl is added with syringe in zero degree3(1ml) then continues stirring 2 hours in zero degree.By compound 5 (0.4g, 0.35mmol)
Dichloroethanes (anhydrous, 10ml) solution be slowly added to, be then heated to and be refluxed overnight.After TLC shows fully reacting, stop anti-
It answers, is as cold as room temperature.Reaction mixture is directly poured into sodium acetate solution, after stirring 2 hours, methylene chloride extraction.Column chromatography
Purification, obtains yellow solid product 0.327g, yield 80%.
The synthesis of compound 7: under nitrogen protection, by compound 6 (0.117g, 0.1mmol), end group (228mg,
It 1mmol) and analyzes in pure chloroform (30ml) addition there-necked flask, air-blowing removes oxygen 10 minutes.Pyridine (1ml) be added, then plus
Heat is refluxed overnight to 75 DEG C.After TLC shows fully reacting, stop reaction, near room temperature.Directly revolving removes chloroform, and first is added
Alcohol collects the dark solid of generation.Then greenish solid product 0.1g, yield 62% are obtained through column Chromatographic purification.
Embodiment 2
The synthesis of compound 8: under nitrogen protection, by compound 6 (0.117g, 0.1mmol), end group (260mg,
It 1mmol) and analyzes in pure chloroform (30ml) addition there-necked flask, air-blowing removes oxygen 10 minutes.Pyridine (1ml) be added, then plus
Heat is refluxed overnight to 75 DEG C.After TLC shows fully reacting, stop reaction, near room temperature.Directly revolving removes chloroform, and first is added
Alcohol collects the dark solid of generation.Then blue solid product 0.11g is obtained through column Chromatographic purification.
Embodiment 3
The synthesis of compound 9: under nitrogen protection, by compound 6 (0.117g, 0.1mmol), end group (230mg,
It 1mmol) and analyzes in pure chloroform (30ml) addition there-necked flask, air-blowing removes oxygen 10 minutes.Pyridine (1ml) be added, then plus
Heat is refluxed overnight to 75 DEG C.After TLC shows fully reacting, stop reaction, near room temperature.Directly revolving removes chloroform, and first is added
Alcohol collects the dark solid of generation.Then blue solid product 0.15g is obtained through column Chromatographic purification.
Embodiment 4
Asymmetric acceptor compound 7,8,9 with synthesis is molecular receptor, and PM6 is donor (being purchased from commercial channel), is blended
It is prepared for photoactive layer, is then prepared for organic solar batteries with the assembling of other components, PM6 structure is as follows:
The preparation process of photoactive layer:
It is donor based on PM6, compound 7,8,9 is the active layer preparation of the binary blends of receptor respectively: will be polymerize
Object sample P M6 and acceptor molecule weight ratio (from 1:1) are dissolved in chloroform, and addition volume fraction is that (1,8- diiodo- is pungent by 0.5%DIO
Alkane), stir about 12 hours at room temperature are placed in glove box, are obtained to the blend solution of receptor, are turned using sol evenning machine in difference
The lower spin-coating film of speed.
Organic solar batteries preparation process is as follows:
The substrate as composed by transparent substrate and transparent conductive cathode ITO to surface roughness less than 1nm carries out clear
It washes, with being dried with nitrogen after cleaning；Commercially available conductive polyelectrolyte (poly- (3, the 4- second of rotary coating on the surface transparent conductive cathode ITO
Alkene dioxy thiophene): poly- (styrene sulfonic acid) (4500rpm, 40s, 40nm) prepares anode buffer layer, and will be formed by film into
Row thermal annealing (100 DEG C, 10min)；Using spin coating preparation donor PM6 and receptor mixed active layer on anode buffer layer
(2000rpm, 60s, 95nm), mass ratio 1:1；In photoactive layer surface spin coating cathode buffer layer acetylacetone,2,4-pentanedione zirconium (2mg/ml second
Alcoholic solution, 5000rpm/min, 8nm)；The evaporation metal cathode Al (100nm) on cathode buffer layer.In standard test condition AM
1.5,100mW/cm2Under to measure property as follows:
Organic solar batteries device parameters of the table 1 based on asymmetric acceptor material
It should be noted that above example is only used to illustrate the technical scheme of the present invention rather than is limited.Although ginseng
It is described the invention in detail according to given example, but those skilled in the art can be as needed to this hair
Bright technical solution is modified or replaced equivalently, without departing from the spirit and scope of the technical solution of the present invention.
Claims (10)
1. a kind of asymmetric non-fullerene small molecule receptor material, which is characterized in that its core skeleton structure of the acceptor material
Formula has following any structure:
Wherein, R1,R2,R4,R5Independently selected from hydrogen atom, alkyl or alkoxy；
The end group structural formula (shown in *) of the core skeleton structural formula has following any structure:
Wherein, R3, R6Independently selected from hydrogen atom, alkyl, alkoxy or halogen, X is selected from oxygen group elements.
2. asymmetric non-fullerene small molecule receptor material as described in claim 1, which is characterized in that R1,R2,R4,R5It is independent
Ground is selected from the alkyl or C1~C22 alkoxy of C1~C20；
Preferably, R1Selected from-C6H13, R2Selected from-C8H17。
3. asymmetric non-fullerene small molecule receptor material as described in claim 1, which is characterized in that the halogen includes F,
Cl, Br, I, preferably Cl；
X is selected from O, S, Se, any one of Te.
4. application of any one of the claim 1-3 asymmetric non-fullerene small molecule receptor material as battery material.
5. application as claimed in claim 4, which is characterized in that the battery is organic solar batteries, and the application is specially
Organic solar active material.
6. application as claimed in claim 5, which is characterized in that the application is organic solar batteries photoactive layer material.
7. a kind of organic solar batteries photoactive layer, which is characterized in that the organic solar batteries photoactive layer includes power
Benefit requires any one of 1-3 asymmetric non-fullerene small molecule receptor material.
8. organic solar batteries photoactive layer as claimed in claim 7, which is characterized in that it further includes donor material；It is excellent
Choosing, the donor material is PM6.
9. a kind of organic solar batteries, which is characterized in that it includes any one of claim 1-3 asymmetric non-fullerene
Small molecule receptor material and/or the organic solar batteries photoactive layer of claim 7 or 8.
10. any one of the claim 1-3 asymmetric non-fullerene small molecule receptor material and/or claim 7-8 are any
Application of the organic solar batteries in photoelectric field described in the item photoactive layer and/or claim 9.
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| CN113185539A (en) * | 2020-01-14 | 2021-07-30 | 中国科学院宁波材料技术与工程研究所 | Ternary ring benzothiadiazole organic small molecular material, preparation method and application thereof |
| CN112552489A (en) * | 2020-11-09 | 2021-03-26 | 山东师范大学 | Asymmetric non-fullerene compound and preparation method and application thereof |
| CN114478569A (en) * | 2021-02-04 | 2022-05-13 | 宁波诺丁汉大学 | Multi-fused-ring conjugated small molecule based on thiophene [3,2-b ] pyrrole and preparation method and application thereof |
| CN113880862A (en) * | 2021-09-09 | 2022-01-04 | 苏州大学 | Non-fullerene receptor with cooperative assembly characteristic and preparation method and application thereof |
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Application publication date: 20191112 |