CN104370682B - Preparation of a kind of methylenecyclopropanes fullerene derivate and uses thereof - Google Patents
Preparation of a kind of methylenecyclopropanes fullerene derivate and uses thereof Download PDFInfo
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- CN104370682B CN104370682B CN201310354249.8A CN201310354249A CN104370682B CN 104370682 B CN104370682 B CN 104370682B CN 201310354249 A CN201310354249 A CN 201310354249A CN 104370682 B CN104370682 B CN 104370682B
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- soccerballene
- methylenecyclopropanes
- fullerene derivate
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- 0 C*C1[C@](C)C2=CC(C3)C(*4)C(*)C4[C@@](C)C3C1C2 Chemical compound C*C1[C@](C)C2=CC(C3)C(*4)C(*)C4[C@@](C)C3C1C2 0.000 description 4
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- 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
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Abstract
The invention discloses a kind of methylenecyclopropanes fullerene derivate, described fullerene derivate has structure shown in logical formula I.The invention also discloses the preparation method and its usage of above-mentioned methylenecyclopropanes fullerene derivate.Described derivative has good solubility, and higher lowest unoccupied molecular orbital (LUMO) energy level and higher electronic mobility, can be applicable to organic solar batteries.
Description
Technical field
The present invention relates to the preparation of a class methylenecyclopropanes fullerene derivate and the application in organic solar batteries thereof.
Background technology
Along with global industry and economic fast development, the mankind increase rapidly for the demand of the energy, and energy dilemma constantly increases the weight of.The current main energy sources fossil oil of mankind approach exhaustion at last; On the other hand, the excessive use of fossil oil also creates negative impact to global climate and environment.Sun power receives much attention as clean reproducible energy, and wherein organic solar batteries obtains develop rapidly in recent years as third generation solar cell.Soccerballene makes its derivative be used widely in organic solar batteries as acceptor material due to the ball-like structure of its uniqueness, electron affinity and conduction property.Wherein, PC
61bM and PC
71bM is two kinds of classical acceptor materials.But PC
61bM and PC
71lowest unoccupied molecular orbital (LUMO) energy level of BM is relatively low, causes battery open circuit voltage (V
oc) lower, limit the raising of cell power conversion efficiency.Therefore, the fullerene acceptor material developing high lumo energy is a large focus to improve cell power conversion efficiency.
Many addition reactions can reduce soccerballene π-electron number, effectively improve the lumo energy of fullerene derivate, thus improve the V of battery
ocand energy conversion efficiency.Current scientist has developed the fullerene acceptor material of multiple 56 π-electrons, and is successfully applied to organic solar batteries.Li Yongfang etc. report based on fullerene derivate IC
70the battery of BA, top efficiency reaches 7.4%(HighEfficiencyPolymerSolarCellsBasedonPoly (3-hexylthiophene)/indene-C
70bisadductwithSolventAdditive, Y.Lietal, EnergyEnviron.Sci.2012,5,7943 ~ 7949).On the other hand, research also shows the increase along with additive group number, and the electronic mobility of soccerballene declines rapidly.This is increasing due to large steric hindrance additive group, and the accumulation of soccerballene is hindered, thus causes electronic mobility to decline, and limits the further raising of device performance.Therefore the fullerene derivate with little steric hindrance additive group is developed significant for the efficient organic solar batteries of development.
Methylenecyclopropanes is minimum group fullerene surface being carried out to chemically modified, because its volume is little, substantially do not affect the accumulation of soccerballene, can improve again the lumo energy of soccerballene, the derivative therefore based on methylenecyclopropanes soccerballene is the very potential acceptor material of a class simultaneously.Therefore, the derivative developed based on methylenecyclopropanes soccerballene is significant for the development in organic solar batteries field.
Summary of the invention
An object of the present invention is to provide a kind of methylenecyclopropanes fullerene derivate, this analog derivative has higher lumo energy and higher electronic mobility, is applied to polymkeric substance (P3HT) solar cell and can obtains effciency of energy transfer higher than 5.5%.
In order to achieve the above object, present invention employs following technical scheme:
A kind of methylenecyclopropanes fullerene derivate, described derivative has structure shown in logical formula I:
Wherein, m is 1,2 or 3; N is 1,2 or 3; Ring F is soccerballene C
60or soccerballene C
70;
for
or
R is selected from hydrogen atom, halogen atom, thiazolinyl, alkynyl, C
1-C
20alkyl, C
1-C
20alkoxyl group, aryl, hydroxyl, amino, carbonyl, ester group, any one in cyano group or nitro.
Preferably, described C
1-C
20alkyl or C
1-C
20alkoxyl group be straight chain, side chain or ring-type.
Preferably, described C
1-C
20alkyl or C
1-C
20alkoxyl group in one or more carbon atoms replaced by Sauerstoffatom, thiazolinyl, alkynyl, aryl, amino, hydroxyl, carbonyl, ester group or nitro.That is, C
1-C
20alkyl or C
1-C
20alkoxyl group can replace by any one in above-mentioned group, this carbonatoms be replace before carbonatoms.
Preferably, described C
1-C
20alkyl or C
1-C
20alkoxyl group in one or more hydrogen atoms replaced by halogen atom, Sauerstoffatom, thiazolinyl, alkynyl, aryl, amino, hydroxyl, carbonyl, ester group or nitro.
Two of object of the present invention is the preparation method providing a kind of above-mentioned methylenecyclopropanes fullerene derivate, and described method comprises the steps:
When
for
or
time, described method is:
(1) compound of general formula (II-VI) described structure and methylenecyclopropanes soccerballene are reacted under iodide and crown ether existent condition, obtain corresponding methylenecyclopropanes fullerene derivate; Described soccerballene is soccerballene C
60or soccerballene C
70;
When
for
time, described method is:
(1 '), by compound general formula (VII) Suo Shi and methylenecyclopropanes soccerballene back flow reaction, obtains corresponding methylenecyclopropanes fullerene derivate; Described soccerballene is soccerballene C
60or soccerballene C
70;
X is selected from chlorine atom or bromine atoms; R is selected from hydrogen atom, halogen atom, thiazolinyl, alkynyl, C
1-C
20alkyl, C
1-C
20alkoxyl group, aryl, hydroxyl, amino, carbonyl, ester group, any one in cyano group or nitro.
Preferably, described C
1-C
20alkyl or C
1-C
20alkoxyl group be straight chain, side chain or ring-type, or one or more carbon atom is replaced by Sauerstoffatom, thiazolinyl, alkynyl, aryl, amino, hydroxyl, carbonyl, ester group or nitro.That is, C
1-C
20alkyl or C
1-C
20alkoxyl group can replace by any one in above-mentioned group, this carbonatoms be replace before carbonatoms.
Preferably, described C
1-C
20alkyl or C
1-C
20alkoxyl group in one or more hydrogen atoms replaced by halogen atom, Sauerstoffatom, thiazolinyl, alkynyl, aryl, amino, hydroxyl, carbonyl, ester group or nitro.
In aforesaid method (1), described temperature of reaction is 80 ~ 150 DEG C, and the reaction times is 2 ~ 24 hours.
Described temperature of reaction is such as 82 DEG C, 87 DEG C, 92 DEG C, 97 DEG C, 102 DEG C, 107 DEG C, 112 DEG C, 117 DEG C, 122 DEG C, 127 DEG C, 132 DEG C, 137 DEG C, 142 DEG C or 148 DEG C.
The described reaction times is such as 3 hours, 5 hours, 7 hours, 9 hours, 11 hours, 13 hours, 15 hours, 17 hours, 19 hours, 21 hours or 23 hours.
In aforesaid method (1), described iodide are potassiumiodide or sodium iodide.
In aforesaid method (1 '), shown in general formula (VII), the mol ratio of compound and methylenecyclopropanes soccerballene is 1 ~ 100:1, such as 5:1,15:1,22:1,29:1,32:1,37:1,43:1,47:1,52:1,58:1,61:1,69:1,72:1,78:1,84:1,88:1,92:1 or 97:1, preferably 4 ~ 96:1, further preferred 9 ~ 90:1.
In aforesaid method (1 '), the described reaction times is 2 ~ 72 hours, such as 3 hours, 8 hours, 15 hours, 22 hours, 29 hours, 34 hours, 39 hours, 43 hours, 48 hours, 52 hours, 57 hours, 62 hours, 67 hours or 71 hours, preferably 4 ~ 68 hours, preferably 7 ~ 61 hours further.
Three of object of the present invention is the purposes providing a kind of methylenecyclopropanes fullerene derivate as above, and described derivative can be used for organic solar batteries.
Compared with prior art, the present invention has following beneficial effect:
The invention provides the methylenecyclopropanes fullerene derivate that a class is novel, and there is higher product.Described fullerene derivate has good solubility, is soluble in common organic solvents, has high lumo energy (>=-3.7eV), higher electronic mobility (>=10
-5cm
2v
-1s
-1) and good thermostability (T
d>=180 DEG C), can for the preparation of high V
ocwith the solar cell of high-energy conversion efficiency, it is the photovoltaic material that a class is excellent.
Accompanying drawing explanation
Technical scheme of the present invention is further illustrated by embodiment below in conjunction with accompanying drawing.
Fig. 1 is the absorption spectrum of fullerene derivate F1 in chloroformic solution that the embodiment of the present invention 1 is synthesized.
Fig. 2 is the thermal gravimetric analysis curve of the fullerene derivate F1 that the embodiment of the present invention 1 is synthesized.
Fig. 3 is the J-V curve of organic solar batteries of the fullerene derivate F1 synthesized based on the embodiment of the present invention 1.
Embodiment
For better the present invention being described, be convenient to understand technical scheme of the present invention, typical but non-limiting embodiment of the present invention is as follows:
The experimental technique used in following embodiment if no special instructions, is ordinary method.
The experiment material used in following experimental example, reagent etc. all obtain by commercial sources or known experimental technique.
Embodiment 1: prepare single methylenecyclopropanes fullerene derivate F1
Synthesis step is as follows:
By 1 of 0.2mmol, 2-xylylene bromide and the mono-methylenecyclopropanes soccerballene of 0.1mmol are dissolved in orthodichlorobenzene, the 18-adding 0.1mmol potassiumiodide and 0.05mmol is again preced with-6-ether, react at 80 DEG C after 24 hours, reaction soln is poured into precipitating in methyl alcohol, gained crude product is crossed silicagel column separation (Er Liuization Tan ︰ normal hexane=1:1, v/v) and obtain black solid F1, productive rate is 61%.The mass spectrographic molecular ion peak of product F1 is 838.3, with (M
+) coupling;
1hNMR(400MHz, CDCl
3): (ppm) 7.47-7.78(m, 4H, Ar), 2.94-4.94(m, 6H, CH
2).
Embodiment 2: prepare dimethylene cyclopropane fullerene derivate F2
Synthesis step is as follows:
By 1 of 0.2mmol, 2-xylylene bromide and 0.1mmol dimethylene cyclopropane soccerballene are dissolved in orthodichlorobenzene, the 18-adding 0.1mmol potassiumiodide and 0.05mmol is again preced with-6-ether, react at 80 DEG C after 24 hours, reaction soln is poured into precipitating in methyl alcohol, gained crude product is crossed silicagel column separation (Er Liuization Tan ︰ normal hexane=1:1, v/v) and obtain brown-red solid F2, productive rate is 50%.The mass spectrographic molecular ion peak of product F2 is 853.1, with (M+H
+) coupling;
1hNMR(400MHz, CDCl
3): (ppm) 7.43-7.72(m, 4H, Ar), 2.97-4.52(m, 8H, CH
2).
Embodiment 3: prepare trimethylene cyclopropane fullerene derivate F3
Synthesis step is as follows:
By 1 of 0.2mmol, 2-xylylene bromide and 0.1mmol trimethylene cyclopropane soccerballene are dissolved in orthodichlorobenzene, the 18-adding 0.1mmol potassiumiodide and 0.05mmol is again preced with-6-ether, react at 80 DEG C after 24 hours, reaction soln is poured into precipitating in methyl alcohol, gained crude product is crossed silicagel column separation (Er Liuization Tan ︰ normal hexane=1:1, v/v) and obtain yellow-brown solid F3, productive rate is 42%.The mass spectrographic molecular ion peak of product F3 is 867.1, with (M+H
+) coupling;
1hNMR(400MHz, CDCl
3): (ppm) 7.40-7.58(m, 4H, Ar), 2.85-4.52(m, 10H, CH
2).
Embodiment 4: prepare single methylenecyclopropanes fullerene derivate F4
Synthesis step is as follows:
Single methylenecyclopropanes soccerballene of 1mmol is dissolved in orthodichlorobenzene, then adds the indenes of 1mmol, be heated to back flow reaction 5 hours.Treat that solution is cooled to room temperature, added precipitating in methyl alcohol.Gained crude product is crossed silicagel column separation (Er Liuization Tan ︰ normal hexane=1:1, v/v) and obtain black solid F4, productive rate is 14%.The mass spectrographic molecular ion peak of product F4 is 851.1, with (M+H
+) coupling;
1hNMR(400MHz, CDCl
3): (ppm) 7.28-7.82(m, 4H, Ar), 2.67-5.16(m, 6H, CH
2and CH).
Embodiment 5: prepare single methylenecyclopropanes soccerballene (C
70) derivative F5
Synthesis step is as follows:
By 1, the 2-xylylene bromide of 0.2mmol and 0.1mmol methylenecyclopropanes soccerballene (C
70) be dissolved in orthodichlorobenzene, the 18-adding 0.1mmol potassiumiodide and 0.05mmol is again preced with-6-ether, react at 80 DEG C after 24 hours, reaction soln is poured into precipitating in methyl alcohol, gained crude product is crossed silicagel column and be separated (Er Liuization Tan ︰ normal hexane=1:1, v/v) obtain black solid F5, productive rate is 54%.The mass spectrographic molecular ion peak of product F5 is 958.1, with (M
+) coupling;
1hNMR(400MHz, CDCl
3): (ppm) 7.25-7.55(m, 4H, Ar), 2.60-4.14(m, 6H, CH
2).
Embodiment 6: prepare single methylenecyclopropanes fullerene derivate F1
Synthesis step is as follows:
By 1 of 0.2mmol, 2-xylylene bromide and the mono-methylenecyclopropanes soccerballene of 0.1mmol are dissolved in orthodichlorobenzene, the 18-adding 0.1mmol potassiumiodide and 0.05mmol is again preced with-6-ether, react at 150 DEG C after 2 hours, reaction soln is poured into precipitating in methyl alcohol, gained crude product is crossed silicagel column separation (Er Liuization Tan ︰ normal hexane=1:1, v/v) and obtain black solid F6, productive rate is 61%.
Embodiment 7: prepare single methylenecyclopropanes fullerene derivate F4
Synthesis step is as follows:
Single methylenecyclopropanes soccerballene of 1mmol is dissolved in orthodichlorobenzene, then adds the indenes of 5mmol, be heated to back flow reaction 2 hours.Treat that solution is cooled to room temperature, added precipitating in methyl alcohol.Gained crude product is crossed silicagel column separation (Er Liuization Tan ︰ normal hexane=1:1, v/v) and obtain black solid F8, productive rate is 34%.
Embodiment 8: prepare single methylenecyclopropanes fullerene derivate F6
Synthesis step is as follows:
Single methylenecyclopropanes soccerballene of 1mmol is dissolved in orthodichlorobenzene, then adds the indenes of 100mmol, be heated to back flow reaction 72 hours.Treat that solution is cooled to room temperature, added precipitating in methyl alcohol.Gained crude product is crossed silicagel column separation (Er Liuization Tan ︰ normal hexane=1:1, v/v) and obtain black solid F6, productive rate is 34%.
Embodiment 9: prepare trimethylene cyclopropane fullerene derivate F7
Synthesis step is as follows:
By 1 of 1.2mmol, 2-xylylene bromide and 0.1mmol trimethylene cyclopropane soccerballene are dissolved in orthodichlorobenzene, the 18-adding 0.1mmol potassiumiodide and 0.05mmol is again preced with-6-ether, react at 80 DEG C after 24 hours, reaction soln is poured into precipitating in methyl alcohol, gained crude product is crossed silicagel column separation (Er Liuization Tan ︰ normal hexane=2:1, v/v) and obtain brown solid F7, productive rate is 25%.
Embodiment 10: prepare the solar cell based on embodiment 1 acceptor material F1
The conductive glass cleaned up (ITO) substrate applies poly-(3,4-ethylene dioxythiophene) (PEDOT)/poly styrene sulfonate (PSS) that one deck 30nm is thick.Orthodichlorobenzene is dissolved in by weight 1:0.6 by gathering the fullerene acceptor material F1 that (3-hexyl thiophene) (P3HT) and embodiment 1 obtain, the concentration obtaining solution is 20mg/mL, and this solution is spun on PEDOT ︰ PSS film as active coating, thickness is about 120nm, then heats 20 minutes at 150 DEG C.By metal Ca evaporation to above-mentioned active coating surface, thickness is 10nm, then by metal A l evaporation on above-mentioned metal Ca, thickness is about 100nm, obtains described solar cell.
At AM1.5G100mW/cm
2under light intensity, the open circuit voltage based on the photovoltaic device of fullerene acceptor material F1 is 0.84V, and short-circuit current is 9.96mA/cm
2, packing factor is 70%, and effciency of energy transfer is 5.9%, and the J-V curve of corresponding device as shown in Figure 3.
Prepare same as above based on the process of the photovoltaic device of embodiment 2 ~ 8 gained fullerene derivate.
Applicant states, the present invention illustrates method detailed of the present invention by above-described embodiment, but the present invention is not limited to above-mentioned method detailed, does not namely mean that the present invention must rely on above-mentioned method detailed and could implement.Person of ordinary skill in the field should understand, any improvement in the present invention, to equivalence replacement and the interpolation of ancillary component, the concrete way choice etc. of each raw material of product of the present invention, all drops within protection scope of the present invention and open scope.
Claims (17)
1. a methylenecyclopropanes fullerene derivate, is characterized in that, described fullerene derivate has structure shown in logical formula I:
Wherein, m is 1,2 or 3; N is 1,2 or 3; Ring F is soccerballene C
60or soccerballene C
70;
for
R is selected from hydrogen atom, halogen atom, thiazolinyl, alkynyl, C
1-C
20alkyl, C
1-C
20alkoxyl group, aryl, hydroxyl, amino, ester group, any one in cyano group or nitro.
2. fullerene derivate as claimed in claim 1, is characterized in that, described C
1-C
20alkyl or C
1-C
20alkoxyl group be straight or branched.
3. fullerene derivate as claimed in claim 2, is characterized in that, described C
1-C
20alkyl or C
1-C
20alkoxyl group in one or more carbon atoms replaced by Sauerstoffatom, thiazolinyl, alkynyl, aryl, amino, hydroxyl, carbonyl, ester group or nitro.
4. fullerene derivate as claimed in claim 2 or claim 3, is characterized in that, described C
1-C
20alkyl or C
1-C
20alkoxyl group in one or more hydrogen atoms replaced by halogen atom, Sauerstoffatom, thiazolinyl, alkynyl, aryl, amino, hydroxyl, carbonyl, ester group or nitro.
5. a preparation method for methylenecyclopropanes fullerene derivate as claimed in claim 1, is characterized in that, described method comprises the steps:
When
for
time, described method is:
(1) compound of general formula (II-VI) described structure and methylenecyclopropanes soccerballene are reacted under iodide and crown ether existent condition, obtain corresponding methylenecyclopropanes fullerene derivate; Described soccerballene is soccerballene C
60or soccerballene C
70;
When
for
time, described method is:
(1 '), by compound general formula (VII) Suo Shi and methylenecyclopropanes soccerballene back flow reaction, obtains corresponding methylenecyclopropanes fullerene derivate; Described soccerballene is soccerballene C
60or soccerballene C
70;
Wherein, X is selected from chlorine atom or bromine atoms, and R is selected from hydrogen atom, halogen atom, thiazolinyl, alkynyl, C
1-C
20alkyl, C
1-C
20alkoxyl group, aryl, hydroxyl, amino, ester group, any one in cyano group or nitro.
6. method as claimed in claim 5, is characterized in that, described C
1-C
20alkyl or C
1-C
20alkoxyl group be straight or branched.
7. method as claimed in claim 6, is characterized in that, described C
1-C
20alkyl or C
1-C
20alkoxyl group in one or more carbon atoms replaced by Sauerstoffatom, thiazolinyl, alkynyl, aryl, amino, hydroxyl, carbonyl, ester group or nitro.
8. method as claimed in claim 6, is characterized in that, described C
1-C
20alkyl or C
1-C
20alkoxyl group in one or more hydrogen atoms replaced by halogen atom, Sauerstoffatom, thiazolinyl, alkynyl, aryl, amino, hydroxyl, carbonyl, ester group or nitro.
9. the method as described in claim 5 or 6, is characterized in that, in method (1), described temperature of reaction is 80 ~ 150 DEG C, and the reaction times is 2 ~ 24 hours.
10. the method as described in one of claim 5-7, is characterized in that, in method (1), described iodide are potassiumiodide or sodium iodide.
11. methods as described in one of claim 5-8, is characterized in that, in method (1 '), shown in general formula (VII), the mol ratio of compound and methylenecyclopropanes soccerballene is 1 ~ 100:1.
12. methods as claimed in claim 11, is characterized in that, in method (1 '), shown in general formula (VII), the mol ratio of compound and methylenecyclopropanes soccerballene is 4 ~ 96:1.
13. methods as claimed in claim 12, is characterized in that, in method (1 '), shown in general formula (VII), the mol ratio of compound and methylenecyclopropanes soccerballene is 9 ~ 90:1.
14. methods as described in one of claim 5-8, it is characterized in that, in method (1 '), the described reaction times is 2 ~ 72 hours.
15. methods as claimed in claim 14, is characterized in that, in method (1 '), the described reaction times is 4 ~ 68 hours.
16. methods as claimed in claim 15, is characterized in that, in method (1 '), the described reaction times is 7 ~ 61 hours.
The purposes of 17. 1 kinds of methylenecyclopropanes fullerene derivates as described in one of claim 1-4, is characterized in that, described derivative is used for organic solar batteries.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101928196A (en) * | 2009-06-19 | 2010-12-29 | 中国科学院化学研究所 | Indene-containing fullerene derivative receptor material and preparation method and use thereof |
| CN101973839A (en) * | 2010-10-27 | 2011-02-16 | 西安近代化学研究所 | Method for preparing indene-C60 mono-addition compound by microwave reaction |
| CN102070133A (en) * | 2009-11-20 | 2011-05-25 | 中国科学院化学研究所 | Indene-containing fullerene derivative acceptor materials and preparation method and application thereof |
| CN102391078A (en) * | 2011-09-01 | 2012-03-28 | 中国科学院化学研究所 | Benzene ring-contained fullerene derivative and preparation method and use thereof |
| CN102911002A (en) * | 2012-10-23 | 2013-02-06 | 中国科学院化学研究所 | Fullerene derivative containing double-benzene nucleus and preparation method and application thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20120004476A1 (en) * | 2009-01-29 | 2012-01-05 | Korea Research Institute Of Chemical Technology | Fullerene Derivatives and Organic Electronic Device Comprising the Same |
-
2013
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101928196A (en) * | 2009-06-19 | 2010-12-29 | 中国科学院化学研究所 | Indene-containing fullerene derivative receptor material and preparation method and use thereof |
| CN102070133A (en) * | 2009-11-20 | 2011-05-25 | 中国科学院化学研究所 | Indene-containing fullerene derivative acceptor materials and preparation method and application thereof |
| CN101973839A (en) * | 2010-10-27 | 2011-02-16 | 西安近代化学研究所 | Method for preparing indene-C60 mono-addition compound by microwave reaction |
| CN102391078A (en) * | 2011-09-01 | 2012-03-28 | 中国科学院化学研究所 | Benzene ring-contained fullerene derivative and preparation method and use thereof |
| CN102911002A (en) * | 2012-10-23 | 2013-02-06 | 中国科学院化学研究所 | Fullerene derivative containing double-benzene nucleus and preparation method and application thereof |
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