CN109988196A - The preparation method and application of (4- ferrocene acetenyl) aniline modified fullerene - Google Patents
The preparation method and application of (4- ferrocene acetenyl) aniline modified fullerene Download PDFInfo
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- CN109988196A CN109988196A CN201910273374.3A CN201910273374A CN109988196A CN 109988196 A CN109988196 A CN 109988196A CN 201910273374 A CN201910273374 A CN 201910273374A CN 109988196 A CN109988196 A CN 109988196A
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- ferrocene
- acetenyl
- modified fullerene
- aniline
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- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 title claims abstract description 83
- -1 aniline modified fullerene Chemical class 0.000 title claims abstract description 63
- 238000002360 preparation method Methods 0.000 title claims abstract description 52
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract description 39
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical class C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000002904 solvent Substances 0.000 claims abstract description 31
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000005406 washing Methods 0.000 claims abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 150000002191 fatty alcohols Chemical class 0.000 claims abstract description 9
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000009835 boiling Methods 0.000 claims abstract description 7
- 239000013078 crystal Substances 0.000 claims description 47
- QMQZIXCNLUPEIN-UHFFFAOYSA-N 1h-imidazole-2-carbonitrile Chemical compound N#CC1=NC=CN1 QMQZIXCNLUPEIN-UHFFFAOYSA-N 0.000 claims description 25
- 206010070834 Sensitisation Diseases 0.000 claims description 19
- 230000008313 sensitization Effects 0.000 claims description 19
- 239000007784 solid electrolyte Substances 0.000 claims description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- 239000003960 organic solvent Substances 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- XGDRLCRGKUCBQL-UHFFFAOYSA-N 1h-imidazole-4,5-dicarbonitrile Chemical compound N#CC=1N=CNC=1C#N XGDRLCRGKUCBQL-UHFFFAOYSA-N 0.000 claims description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 238000001914 filtration Methods 0.000 claims description 7
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 7
- 239000012074 organic phase Substances 0.000 claims description 7
- 238000000926 separation method Methods 0.000 claims description 7
- 239000000654 additive Substances 0.000 claims description 6
- 230000000996 additive effect Effects 0.000 claims description 6
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 4
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 claims description 4
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 claims description 4
- 235000019441 ethanol Nutrition 0.000 claims description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 4
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- HITWHALOZBMLHY-UHFFFAOYSA-N 2-Butyl-1H-benzimidazole Chemical compound C1=CC=C2NC(CCCC)=NC2=C1 HITWHALOZBMLHY-UHFFFAOYSA-N 0.000 claims description 3
- 150000001336 alkenes Chemical class 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- 230000002195 synergetic effect Effects 0.000 claims description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 239000004593 Epoxy Substances 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000001294 propane Substances 0.000 claims 1
- 239000003792 electrolyte Substances 0.000 description 23
- 239000000975 dye Substances 0.000 description 20
- 229910003472 fullerene Inorganic materials 0.000 description 8
- 150000003851 azoles Chemical class 0.000 description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 5
- RAFSTXGDSLCINC-UHFFFAOYSA-N 1-ethylimidazole-4,5-dicarbonitrile Chemical compound CCN1C=NC(C#N)=C1C#N RAFSTXGDSLCINC-UHFFFAOYSA-N 0.000 description 4
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000000306 component Substances 0.000 description 3
- 150000002460 imidazoles Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- OFFSQYWTNQVPPN-UHFFFAOYSA-N 1-butylimidazole-4,5-dicarbonitrile Chemical compound C(CCC)N1C=NC(=C1C#N)C#N OFFSQYWTNQVPPN-UHFFFAOYSA-N 0.000 description 2
- SUOVGHDPXJUFME-UHFFFAOYSA-N 1-methylimidazole-4,5-dicarbonitrile Chemical compound CN1C=NC(C#N)=C1C#N SUOVGHDPXJUFME-UHFFFAOYSA-N 0.000 description 2
- KGQZNAHBOCPMLV-UHFFFAOYSA-N 1-propylimidazole-4,5-dicarbonitrile Chemical compound CCCn1cnc(C#N)c1C#N KGQZNAHBOCPMLV-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 238000005538 encapsulation Methods 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- YWNYZQTZOONLGU-UHFFFAOYSA-N C(CC)Cl.[O] Chemical compound C(CC)Cl.[O] YWNYZQTZOONLGU-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- SIXOAUAWLZKQKX-UHFFFAOYSA-N carbonic acid;prop-1-ene Chemical compound CC=C.OC(O)=O SIXOAUAWLZKQKX-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000008358 core component Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000011245 gel electrolyte Substances 0.000 description 1
- 229910021389 graphene Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000011244 liquid electrolyte Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000005622 photoelectricity Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
- C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic Table
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/20—Light-sensitive devices
- H01G9/2004—Light-sensitive devices characterised by the electrolyte, e.g. comprising an organic electrolyte
- H01G9/2009—Solid electrolytes
-
- 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
- Y02E10/542—Dye sensitized solar cells
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Engineering & Computer Science (AREA)
- Power Engineering (AREA)
- Organic Chemistry (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Hybrid Cells (AREA)
- Photovoltaic Devices (AREA)
Abstract
The invention discloses the preparation methods of (4- ferrocene acetenyl) aniline modified fullerene, include the following steps: the preparation of 1) epoxy-modified fullerene: dispersing amino modified fullerene in fatty alcohol, and epoxychloropropane and potassium hydroxide are added thereto, it flows back and is stirred to react 5-8 hours at 70-80 DEG C, revolving removes solvent, it uses water centrifuge washing 5-7 times afterwards, is placed in baking in 100-110 DEG C of vacuum oven and obtains epoxy-modified fullerene；2) it the preparation of (4- ferrocene acetenyl) aniline modified fullerene: disperses epoxy-modified fullerene in high boiling solvent, (4- ferrocene acetenyl) aniline is added thereto again, it is stirred to react at 70-80 DEG C 6-8 hours, revolving removes solvent, it uses methylene chloride centrifuge washing 6-8 times afterwards, obtains (4- ferrocene acetenyl) aniline modified fullerene.(4- ferrocene acetenyl) the aniline modified fullerene can apply to the dye-sensitized solar cells of preparation high efficiency and high stability.
Description
Technical field
The present invention is Chinese patent " a kind of used by dye sensitization solar battery solid electrolyte based on ionic crystals "
Divisional application, the applying date are on 2 15th, 2018, and application No. is 201810152492.4.The invention belongs to solar battery skills
Art field is related to a kind of dye-sensitized solar cells component, specifically, being related to a kind of dye sensitization based on ionic crystals
Solid electrolyte used for solar batteries.
Background technique
With the energy worsening shortages and environmental problem it is outstanding day by day, the exploitation of clean reproducible energy increasingly by
The concern of people also deepens continuously to the research of clean reproducible energy device solar battery.Dye-sensitized solar cells
As one of numerous solar batteries, paid close attention in the industry since it has the advantages that high efficiency, low cost become in recent years
Focus.
Electrolyte is the core component of dye-sensitized solar cells, mainly undertakes transmission redox couple, excites light
The superiority and inferiority of the effect of reducing dyes, performance directly affects solar battery efficiency and service life cycle.In the prior art often
The electrolyte for dye-sensitized solar cell seen has the diversified forms such as liquid, quasi- solid-state, solid-state.Wherein liquid electrolyte is general
Containing inorganic or organic iodide, iodine, additive and organic solvent etc., have conductivity high, ion diffusion velocity is fast, to more
The advantages that hole light anode good penetrability, but there is easy leakage, volatile, difficult encapsulation, high toxicity, stability difference and dyestuff legibility in it
The disadvantages of absorption；Due to containing a small amount of ethylene carbonate, propene carbonate, ionic liquid equal solvent in quasi-solid electrolyte,
The problem of there are still easy leakages, difficult encapsulation.Solid electrolyte has good long-time stability, but its conductivity is lower, leads
The dye-sensitized solar cells incident photon-to-electron conversion efficiency of solid electrolyte of applying preparation is lower.
Therefore, seek more efficient way, prepare while having the dye sensitization sun of high efficiency and high stability
Energy electrolyte for batteries has extensive market value and commercial applications prospect.
Summary of the invention
In order to overcome the defects of the prior art, the present invention provides a kind of dye sensitization of solar electricity based on ionic crystals
Pond solid electrolyte, which is easy to get, cheap；With dye sensitization of solar disclosed in the prior art
Cell electrolyte is compared, and conductivity is higher, and stability is more preferable, is easier to encapsulate, and is free of organic solvent, and safety is more preferable, and to mentioning
High dye-sensitized solar cells incident photon-to-electron conversion efficiency and job stability are more effective.
To achieve the above object of the invention, the technical solution adopted by the present invention is that, a kind of dye sensitization based on ionic crystals
Solid electrolyte used for solar batteries, the component including following parts by weight: 40-50 parts of cyanoimidazole type ionic crystals, (bis- cyclopentadienyl of 4-
Iron acetenyl) it is fullerene 3-7 parts aniline modified, 5-10 parts of elemental iodine, 5-10 parts of additive.
Preferably, the additive is tolimidazole (MBI), butyl benzimidazole (NBB), tert .-butylpyridine
One or more of (TBP).
Preferably, the preparation method of the cyanoimidazole type ionic crystals, includes the following steps:
1) preparation of 1- alkyl -4,5- dicyano imidazole: 4,5- dicyano imidazole is dissolved in organic solvent, after thereto
Alkane iodide and basic catalyst is added, is stirred to react at 40-60 DEG C 8-10 hour, after by filtering, into reaction system
Water is added, liquid separation takes organic phase, and revolving removes organic solvent step, obtains 1- alkyl -4,5- dicyano imidazole；
2) preparation of cyanoimidazole type ionic crystals: the 1- alkyl -4,5- dicyano miaow that will be prepared by step 1)
Azoles is dissolved in ether, and addition and identical alkane iodide in step 1) thereto, is stirred to react at 40-50 DEG C 6-8 hours,
It is washed 5-7 times with ethyl acetate afterwards, revolving removes solvent.
Preferably, the quality of 4,5- dicyano imidazole described in step 1), organic solvent, alkane iodide, basic catalyst
Than for 1:(10-15): (1.5-2): (0.5-1).
Preferably, the organic solvent is selected from one or both of acetonitrile, chloroform；The basic catalyst is selected from hydrogen-oxygen
Change one or more of sodium, potassium hydroxide, sodium carbonate, potassium carbonate.
Preferably, the alkane iodide is selected from one or more of iodomethane, iodoethane, 1- iodopropane, 1- iodobutane.
Preferably, the dicyano imidazole of 1- alkyl -4,5- described in step 2), ether, alkane iodide mass ratio be (1.5-
2): (6-10): 1.
Preferably, the preparation method of described (4- ferrocene acetenyl) the aniline modified fullerene, includes the following steps:
1) it the preparation of epoxy-modified fullerene: disperses amino modified fullerene in fatty alcohol, and ring is added thereto
Oxygen chloropropane and potassium hydroxide flow back at 70-80 DEG C and are stirred to react 5-8 hours, and revolving removes solvent, use water centrifuge washing afterwards
It 5-7 times, is placed in baking in 100-110 DEG C of vacuum oven and obtains epoxy-modified fullerene；
2) it the preparation of (4- ferrocene acetenyl) aniline modified fullerene: will be prepared by step 1) epoxy-modified
Fullerene is scattered in high boiling solvent, then (4- ferrocene acetenyl) aniline is added thereto, is stirred to react at 70-80 DEG C
6-8 hours, revolving removed solvent, rear to use methylene chloride centrifuge washing 6-8 times, obtained (4- ferrocene acetenyl) aniline modified richness
Strangle alkene.
Preferably, the mass ratio of amino modified fullerene, fatty alcohol, epoxychloropropane, potassium hydroxide described in step 1)
For (3-5): (15-20): (1-2): 1.
Preferably, the fatty alcohol is selected from one or more of ethyl alcohol, isopropanol, n-butanol.
Preferably, the matter of epoxy-modified fullerene described in step 2), high boiling solvent, (4- ferrocene acetenyl) aniline
Amount is than being (3-6): (15-20): 1.
Preferably, the high boiling solvent is in dimethyl sulfoxide, N-Methyl pyrrolidone, n,N-Dimethylformamide
It is one or more of.
A kind of dye-sensitized solar cells, using the used by dye sensitization solar battery solid-state based on ionic crystals
Electrolyte is as electrolyte.
The beneficial effects of adopting the technical scheme are that
1) a kind of electrolyte for dye-sensitized solar cell based on ionic crystals provided by the invention is in solid-state, is free of
There is organic solvent, leakage problem is not present, is conducive to improve dye-sensitized solar cells job stability.
2) electrolyte for dye-sensitized solar cell provided by the invention based on ionic crystals, while being added to cyano
Imidazole type ionic crystals and (4- ferrocene acetenyl) aniline modified fullerene, the two synergistic effect, so that prepared electrolysis
Matter has excellent conductivity, and can effectively improve the dye-sensitized solar cells photoelectric conversion effect using the solid electrolyte
Rate overcomes the lower technical problem of conventional solid-state electrolytic conductivity.
3) electrolyte for dye-sensitized solar cell provided by the invention based on ionic crystals adds cyanoimidazole type
Ionic crystals, this ionic crystals are connected with cyano on imidazole ring, conjugated structure are constituted together with imidazole ring, are conducive to improve
Freeze thaw stability can also improve the performance of electrolyte, enhance the conductive capability and ionic mobility of electrolyte, and reason is
The ionic crystals is rich in electron group or strong electron-withdrawing group group, can be effectively acted in electrolyte by these functional groups
Ion (such as: with oxidation electricity to reacting) or working electrode is (such as: making TiO2Flat-band potential moves), in addition with to electrode
A little interactions occur for (enhancing its catalytic performance).
4) electrolyte for dye-sensitized solar cell provided by the invention based on ionic crystals is added to (bis- cyclopentadienyl of 4-
Iron acetenyl) aniline modified fullerene, ferrocene alkynyl, aniline and fullerene can enhance conductivity, with cyanoimidazole type from
Sub- crystal is applied in dye-sensitized solar cells together, can improve the open-circuit voltage and short circuit current of battery simultaneously, from
And largely improve the photoelectric conversion efficiency of battery.
Specific embodiment
In order to make those skilled in the art more fully understand technical solution of the present invention, and make features described above of the invention,
Purpose and advantage are more clear understandable, and the present invention will be further explained with reference to the examples below.Embodiment is only used for
It is bright the present invention rather than limit the scope of the invention.
The present invention (4- ferrocene acetenyl) aniline as used in the following examples is that oneself is synthesized, and is synthesized referring to king
Lin Ping is studied, Hunan Normal University based on (4- ferrocene acetenyl) aniline/graphene complex electrochemical sensor.Its
His raw material is from upper Haiquan sunrise foreign trade Co., Ltd.
Embodiment 1
A kind of used by dye sensitization solar battery solid electrolyte based on ionic crystals, the group including following parts by weight
Point: 40 parts of cyanoimidazole type ionic crystals, aniline modified 3 parts of fullerene of (4- ferrocene acetenyl), and 5 parts of elemental iodine, methylbenzene
And 5 parts of imidazoles (MBI).
The preparation method of the cyanoimidazole type ionic crystals, includes the following steps:
1) preparation of 1- methyl -4,5- dicyano imidazole: 4,5- dicyano imidazole 10g is dissolved in acetonitrile 100g, backward
Wherein be added iodomethane 15g and sodium hydroxide 5g, be stirred to react at 40 DEG C 8 hours, after by filtering, into reaction system plus
Enter water, liquid separation takes organic phase, and revolving removes organic solvent step, obtains 1- methyl -4,5- dicyano imidazole；
2) preparation of cyanoimidazole type ionic crystals: the 1- methyl -4,5- dicyano miaow that will be prepared by step 1)
Azoles 15g is dissolved in ether 60g, and addition and iodomethane 10g in step 1) thereto, is stirred to react at 40 DEG C 6 hours, rear to use
Ethyl acetate washs 5 times, and revolving removes solvent.
The preparation method of (4- ferrocene acetenyl) the aniline modified fullerene, includes the following steps:
1) preparation of epoxy-modified fullerene: dispersing amino modified fullerene 30g in ethyl alcohol 150g, and adds thereto
Enter epoxychloropropane 10g and potassium hydroxide 10g, flow back and be stirred to react 5 hours at 70 DEG C, revolving remove solvent, afterwards with water from
The heart washs 5 times, is placed in baking in 100 DEG C of vacuum oven and obtains epoxy-modified fullerene；
2) it the preparation of (4- ferrocene acetenyl) aniline modified fullerene: will be prepared by step 1) epoxy-modified
Fullerene 30g is scattered in dimethyl sulfoxide 150g, then (4- ferrocene acetenyl) aniline 10g is added thereto, is stirred at 70 DEG C
Reaction 6 hours is mixed, revolving removes solvent, and it is rear to use methylene chloride centrifuge washing 6 times, it is aniline modified to obtain (4- ferrocene acetenyl)
Fullerene.
A kind of dye-sensitized solar cells, using the used by dye sensitization solar battery solid-state based on ionic crystals
Electrolyte is as electrolyte.
Embodiment 2
A kind of used by dye sensitization solar battery solid electrolyte based on ionic crystals, the group including following parts by weight
Point: 43 parts of cyanoimidazole type ionic crystals, aniline modified 4 parts of fullerene of (4- ferrocene acetenyl), and 7 parts of elemental iodine, butyl benzene
And 6 parts of imidazoles (NBB).
The preparation method of the cyanoimidazole type ionic crystals, includes the following steps:
1) preparation of 1- ethyl -4,5- dicyano imidazole: 4,5- dicyano imidazole 10g is dissolved in chloroform 120g, backward
Wherein be added iodoethane 17g and potassium hydroxide 6g, be stirred to react at 45 DEG C 8.5 hours, after by filtering, into reaction system
Water is added, liquid separation takes organic phase, and revolving removes organic solvent step, obtains 1- ethyl -4,5- dicyano imidazole；
2) preparation of cyanoimidazole type ionic crystals: the 1- ethyl -4,5- dicyano miaow that will be prepared by step 1)
Azoles 17g is dissolved in ether 78g, and addition and iodoethane 10g in step 1) thereto, is stirred to react at 43 DEG C 6.5 hours, after
It is washed 6 times with ethyl acetate, revolving removes solvent.
The preparation method of (4- ferrocene acetenyl) the aniline modified fullerene, includes the following steps:
1) it the preparation of epoxy-modified fullerene: disperses amino modified fullerene 35g in isopropanol 165g, and thereto
Be added epoxychloropropane 13g and potassium hydroxide 10g, flow back and is stirred to react 7 hours at 73 DEG C, revolving removing solvent, after use water
It centrifuge washing 6 times, is placed in baking in 104 DEG C of vacuum oven and obtains epoxy-modified fullerene；
2) it the preparation of (4- ferrocene acetenyl) aniline modified fullerene: will be prepared by step 1) epoxy-modified
Fullerene 40g is scattered in N-Methyl pyrrolidone 175g, then (4- ferrocene acetenyl) aniline 10g is added thereto, 75
It being stirred to react at DEG C 7 hours, revolving removes solvent, and it is rear to use methylene chloride centrifuge washing 7 times, obtain (4- ferrocene acetenyl) benzene
Amine modified fullerenes.
A kind of dye-sensitized solar cells, using the used by dye sensitization solar battery solid-state based on ionic crystals
Electrolyte is as electrolyte.
Embodiment 3
A kind of used by dye sensitization solar battery solid electrolyte based on ionic crystals, the group including following parts by weight
Point: 46 parts of cyanoimidazole type ionic crystals, aniline modified 5 parts of fullerene of (4- ferrocene acetenyl), and 7 parts of elemental iodine, tert-butyl
7 parts of pyridine (TBP).
The preparation method of the cyanoimidazole type ionic crystals, includes the following steps:
1) preparation of 1- propyl -4,5- dicyano imidazole: 4,5- dicyano imidazole 10g is dissolved in acetonitrile 135g, backward
Wherein be added 1- iodopropane 18g and sodium carbonate 7.5g, be stirred to react at 50 DEG C 9 hours, after by filtering, into reaction system
Water is added, liquid separation takes organic phase, and revolving removes organic solvent step, obtains 1- propyl -4,5- dicyano imidazole；
2) preparation of cyanoimidazole type ionic crystals: the 1- propyl -4,5- dicyano miaow that will be prepared by step 1)
Azoles 18g is dissolved in ether 80g, and thereto be added 1- iodopropane 10g, be stirred to react at 46 DEG C 7 hours, after use ethyl acetate
Washing 6 times, revolving remove solvent.
The preparation method of (4- ferrocene acetenyl) the aniline modified fullerene, includes the following steps:
1) it the preparation of epoxy-modified fullerene: disperses amino modified fullerene 40g in n-butanol 180g, and thereto
Be added epoxychloropropane 18g and potassium hydroxide 10g, flow back and is stirred to react 7 hours at 76 DEG C, revolving removing solvent, after use water
It centrifuge washing 7 times, is placed in baking in 106 DEG C of vacuum oven and obtains epoxy-modified fullerene；
2) it the preparation of (4- ferrocene acetenyl) aniline modified fullerene: will be prepared by step 1) epoxy-modified
Fullerene 50g is scattered in n,N-Dimethylformamide 185g, then (4- ferrocene acetenyl) aniline 10g is added thereto,
It being stirred to react at 77 DEG C 7 hours, revolving removes solvent, and it is rear to use methylene chloride centrifuge washing 7 times, obtain (4- ferrocene acetenyl)
Aniline modified fullerene.
A kind of dye-sensitized solar cells, using the used by dye sensitization solar battery solid-state based on ionic crystals
Electrolyte is as electrolyte.
Embodiment 4
A kind of used by dye sensitization solar battery solid electrolyte based on ionic crystals, the group including following parts by weight
Point: 48 parts of cyanoimidazole type ionic crystals, aniline modified 6 parts of fullerene of (4- ferrocene acetenyl), and 8 parts of elemental iodine, additive 8
Part；The additive be tolimidazole (MBI), butyl benzimidazole (NBB), tert .-butylpyridine (TBP) in mass ratio
2:3:5 mixture forms.
The preparation method of the cyanoimidazole type ionic crystals, includes the following steps:
1) preparation of 1- butyl -4,5- dicyano imidazole: 4,5- dicyano imidazole 10g is dissolved in chloroform 142g, backward
Wherein be added 1- iodobutane 19g and potassium carbonate 9g, be stirred to react at 55 DEG C 9.5 hours, after by filtering, into reaction system
Water is added, liquid separation takes organic phase, and revolving removes organic solvent step, obtains 1- butyl -4,5- dicyano imidazole；
2) preparation of cyanoimidazole type ionic crystals: the 1- butyl -4,5- dicyano miaow that will be prepared by step 1)
Azoles 19g is dissolved in ether 93g, and 1- iodobutane 10g is added thereto, is stirred to react at 48 DEG C 7.5 hours, uses acetic acid second afterwards
Ester washs 7 times, and revolving removes solvent.
The preparation method of (4- ferrocene acetenyl) the aniline modified fullerene, includes the following steps:
1) it the preparation of epoxy-modified fullerene: disperses amino modified fullerene 45g in fatty alcohol 190g, and thereto
Epoxychloropropane 18.5g and potassium hydroxide 10g is added, flows back and is stirred to react 7.5 hours at 78 DEG C, revolving removes solvent, after
With water centrifuge washing 6 times, it is placed in baking in 108 DEG C of vacuum oven and obtains epoxy-modified fullerene；The fatty alcohol is second
Alcohol, isopropanol, n-butanol 1:2:4 mixture in mass ratio form.
2) it the preparation of (4- ferrocene acetenyl) aniline modified fullerene: will be prepared by step 1) epoxy-modified
Fullerene 58g is scattered in N-Methyl pyrrolidone 190g, then (4- ferrocene acetenyl) aniline 10g is added thereto, 78
It being stirred to react at DEG C 7.5 hours, revolving removes solvent, and it is rear to use methylene chloride centrifuge washing 8 times, obtain (4- ferrocene acetenyl)
Aniline modified fullerene.
A kind of dye-sensitized solar cells, using the used by dye sensitization solar battery solid-state based on ionic crystals
Electrolyte is as electrolyte.
Embodiment 5
A kind of used by dye sensitization solar battery solid electrolyte based on ionic crystals, the group including following parts by weight
Point: 50 parts of cyanoimidazole type ionic crystals, aniline modified 7 parts of fullerene of (4- ferrocene acetenyl), and 10 parts of elemental iodine, butyl benzene
And 10 parts of imidazoles (NBB).
The preparation method of the cyanoimidazole type ionic crystals, includes the following steps:
1) preparation of 1- ethyl -4,5- dicyano imidazole: 4,5- dicyano imidazole 10g is dissolved in chloroform 150g, backward
Iodoethane 20g and basic catalyst 10g is wherein added, is stirred to react at 60 DEG C 10 hours, after by filtering, to reaction system
Middle addition water, liquid separation take organic phase, and revolving removes organic solvent step, obtains 1- ethyl -4,5- dicyano imidazole；The alkalinity
Catalyst is that sodium hydroxide, sodium carbonate 3:5 mixture in mass ratio form.
2) preparation of cyanoimidazole type ionic crystals: the 1- ethyl -4,5- dicyano miaow that will be prepared by step 1)
Azoles 20g is dissolved in ether 100g, and addition and identical iodoethane 10g in step 1) thereto, and it is small to be stirred to react 8 at 50 DEG C
When, after washed 7 times with ethyl acetate, revolving remove solvent.
The preparation method of (4- ferrocene acetenyl) the aniline modified fullerene, includes the following steps:
1) it the preparation of epoxy-modified fullerene: disperses amino modified fullerene 50g in isopropanol 200g, and thereto
Be added epoxychloropropane 20g and potassium hydroxide 10g, flow back and is stirred to react 8 hours at 80 DEG C, revolving removing solvent, after use water
It centrifuge washing 7 times, is placed in baking in 110 DEG C of vacuum oven and obtains epoxy-modified fullerene；
2) it the preparation of (4- ferrocene acetenyl) aniline modified fullerene: will be prepared by step 1) epoxy-modified
Fullerene 60g is scattered in n,N-Dimethylformamide 200g, then (4- ferrocene acetenyl) aniline 10g is added thereto,
It being stirred to react at 80 DEG C 8 hours, revolving removes solvent, and it is rear to use methylene chloride centrifuge washing 8 times, obtain (4- ferrocene acetenyl)
Aniline modified fullerene.
A kind of dye-sensitized solar cells, using the used by dye sensitization solar battery solid-state based on ionic crystals
Electrolyte is as electrolyte.
Comparative example 1
This example provides a kind of solid electrolyte, component with it is essentially identical in embodiment 1, unlike: be wherein free of
There is (4- ferrocene acetenyl) aniline modified fullerene.
Comparative example 2
This example provides a kind of solid electrolyte, is prepared into according to 13 method of Chinese invention patent CN102592832A embodiment
It arrives.
Quasi-solid electrolyte described in embodiment 1-5 and comparative example 1-2 is dripped into light anode dyestuff titanium dioxide film while hot
Between Pt electrode, further heating is filled out by vacuum so that gel electrolyte completely penetrates in titanium dioxide film perforated membrane
Technical form dye-sensitized solar cells is filled, at 25 DEG C, uses xenon lamp simulated solar irradiation, light intensity 100mW/cm2Under the conditions of,
Measure battery (effective area 0.16cm2) photoelectric parameter is shown in Table 1.
1 dye-sensitized solar cells photoelectric properties parameter of table
As can be seen from the above table, solid electrolyte disclosed by the embodiments of the present invention is assembled into dye-sensitized solar cells
Afterwards, solar cell photoelectric transfer efficiency is between 6.52-7.22%, significantly larger than 1 incident photon-to-electron conversion efficiency 3.85% of comparative example,
As it can be seen that solid electrolyte disclosed by the embodiments of the present invention is conducive to improve the incident photon-to-electron conversion efficiency etc. of dye-sensitized solar cells
The addition of optical property, (4- ferrocene acetenyl) aniline modified fullerene turns the photoelectricity for improving dye-sensitized solar cells
Changing efficiency, open-circuit voltage and short circuit current has facilitation.
The basic principles, main features and advantages of the present invention have been shown and described above.The technology of the industry
Personnel are it should be appreciated that the present invention is not limited to the above embodiments, and what is described in the above embodiment and the description is only the present invention
Principle, various changes and improvements may be made to the invention without departing from the spirit and scope of the present invention, these variation and
Improvement is both fallen in the range of claimed invention.The present invention claims protection scope by appended claims and its
Equivalent defines.
Claims (10)
- The preparation method of (1. 4- ferrocene acetenyl) aniline modified fullerene, which comprises the steps of:1) preparation of epoxy-modified fullerene: dispersing amino modified fullerene in fatty alcohol, and epoxy chlorine is added thereto Propane and potassium hydroxide flow back at 70-80 DEG C and are stirred to react 5-8 hours, and revolving removes solvent, use water centrifuge washing 5-7 afterwards It is secondary, it is placed in baking in 100-110 DEG C of vacuum oven and obtains epoxy-modified fullerene；2) preparation of (4- ferrocene acetenyl) aniline modified fullerene: the epoxy-modified fowler that will be prepared by step 1) Alkene is scattered in high boiling solvent, then (4- ferrocene acetenyl) aniline is added thereto, is stirred to react 6-8 at 70-80 DEG C Hour, revolving removes solvent, and it is rear to use methylene chloride centrifuge washing 6-8 times, obtain (4- ferrocene acetenyl) aniline modified fowler Alkene.
- 2. the preparation method of (4- ferrocene acetenyl) aniline modified fullerene according to claim 1, which is characterized in that Amino modified fullerene described in step 1), fatty alcohol, epoxychloropropane, potassium hydroxide mass ratio be (3-5): (15-20): (1-2): 1；Epoxy-modified fullerene described in step 2), high boiling solvent, (4- ferrocene acetenyl) aniline mass ratio be (3-6): (15-20): 1.
- 3. the preparation method of (4- ferrocene acetenyl) aniline modified fullerene according to claim 1, which is characterized in that The fatty alcohol is selected from one or more of ethyl alcohol, isopropanol, n-butanol；The high boiling solvent is selected from dimethyl sulfoxide, N- One or more of methyl pyrrolidone, N,N-dimethylformamide.
- The application method of (4. 4- ferrocene acetenyl) aniline modified fullerene, which is characterized in that (the 4- ferrocene acetylene Base) aniline modified fullerene can apply to the dye-sensitized solar cells of preparation high efficiency and high stability.
- 5. the application method of (4- ferrocene acetenyl) aniline modified fullerene according to claim 4, which is characterized in that (4- ferrocene acetenyl) the aniline modified fullerene is applied to the dye sensitization sun together with cyanoimidazole type ionic crystals Energy battery, can generate synergistic effect, improve the open-circuit voltage, short circuit current and photoelectric conversion efficiency of battery, have battery excellent Different conductivity.
- 6. the application method of (4- ferrocene acetenyl) aniline modified fullerene according to claim 5, which is characterized in that The preparation method of the cyanoimidazole type ionic crystals, includes the following steps:1) preparation of 1- alkyl -4,5- dicyano imidazole: 4,5- dicyano imidazole is dissolved in organic solvent, after be added thereto Alkane iodide and basic catalyst are stirred to react 8-10 hours at 40-60 DEG C, after by filtering, be added into reaction system Water, liquid separation take organic phase, and revolving removes organic solvent step, obtains 1- alkyl -4,5- dicyano imidazole；2) preparation of cyanoimidazole type ionic crystals: the 1- alkyl -4,5- dicyano imidazole that will be prepared by step 1) is molten In ether, and addition and identical alkane iodide in step 1) thereto, it is stirred to react at 40-50 DEG C 6-8 hours, it is rear to use Ethyl acetate washs 5-7 times, and revolving removes solvent.
- 7. the application method of (4- ferrocene acetenyl) aniline modified fullerene according to claim 6, which is characterized in that 4,5- dicyano imidazole described in step 1), organic solvent, alkane iodide, basic catalyst mass ratio be 1:(10-15): (1.5-2): (0.5-1)；- the 4,5- of 1- alkyl described in step 2) dicyano imidazole, ether, alkane iodide mass ratio be (1.5-2): (6-10): 1.
- 8. the application method of (4- ferrocene acetenyl) aniline modified fullerene according to claim 6, which is characterized in that The organic solvent is selected from one or both of acetonitrile, chloroform；The basic catalyst be selected from sodium hydroxide, potassium hydroxide, One or more of sodium carbonate, potassium carbonate；The alkane iodide is in iodomethane, iodoethane, 1- iodopropane, 1- iodobutane One or more.
- 9. according to the application method of described in any item (4- ferrocene acetenyl) the aniline modified fullerenes of claim 4-8, It is characterized in that, described (4- ferrocene acetenyl) the aniline modified fullerene and cyanoimidazole type ionic crystals, elemental iodine, addition (3-7) is pressed in agent: (40-50): (5-10): the weight of (5-10) can prepare a kind of dye sensitization based on ionic crystals Solid electrolyte used for solar batteries.
- 10. the application method of (4- ferrocene acetenyl) aniline modified fullerene according to claim 9, feature exist In the additive is one or more of tolimidazole, butyl benzimidazole, tert .-butylpyridine.
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| CN103366966A (en) * | 2013-07-04 | 2013-10-23 | 苏州大学 | Solid electrolyte for dye sensitization solar battery based on ion crystal |
| CN103413682A (en) * | 2013-07-26 | 2013-11-27 | 苏州大学 | Quasi-solid electrolyte for solar cell based on double-imidazole type ionic crystal |
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| KR100869802B1 (en) * | 2006-11-17 | 2008-11-21 | 삼성에스디아이 주식회사 | Electrolyte composition for dye-sensitized solar cell, and dye-sensitized solar cell comprising same and method of preparing same |
| KR100997843B1 (en) * | 2008-08-29 | 2010-12-01 | 주식회사 솔켐 | Dye-Sensitized Solar Cells Comprising Solid-State Electrolyte Containing Electrospun Polymer Nanofibers and The Preparing Method of The Same |
| CN101436467B (en) * | 2008-12-15 | 2012-05-16 | 中国科学院长春应用化学研究所 | Ion liquid electrolyte containing bi-(fluorosulfonic acid) imines ion and iodine ion, and application thereof |
| JP5417630B2 (en) * | 2009-07-08 | 2014-02-19 | 綜研化学株式会社 | Composition for solid electrolyte and solar cell using the same |
| US9663734B2 (en) * | 2011-04-02 | 2017-05-30 | Bcr Science Pllc | Solutions of allotropes of carbon and methods of making and using the same |
| CN104867679B (en) * | 2015-05-27 | 2017-12-26 | 中国科学院化学研究所 | A kind of functional nanoparticle and preparation method and application |
| CN105244169B (en) * | 2015-10-21 | 2016-08-17 | 景德镇陶瓷大学 | A kind of quasi-solid electrolyte for DSSC and preparation method thereof |
| CN105390294B (en) * | 2015-12-24 | 2018-01-30 | 上海博暄能源科技有限公司 | A kind of quasi-solid electrolyte used for solar batteries based on Bis-imidazole ionic crystal |
| CN105405667B (en) * | 2015-12-24 | 2018-01-30 | 上海博暄能源科技有限公司 | A kind of used by dye sensitization solar battery solid electrolyte based on ionic crystals |
| CN106653376A (en) * | 2016-12-30 | 2017-05-10 | 湖北工程学院 | Quasi solid electrolyte used for dye sensitized solar cell and preparation method thereof |
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| CN103366966A (en) * | 2013-07-04 | 2013-10-23 | 苏州大学 | Solid electrolyte for dye sensitization solar battery based on ion crystal |
| CN103413682A (en) * | 2013-07-26 | 2013-11-27 | 苏州大学 | Quasi-solid electrolyte for solar cell based on double-imidazole type ionic crystal |
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