CN108359266B - Dibenzo dithieno pyrylium dyes and its application in dye-sensitized solar cells - Google Patents
Dibenzo dithieno pyrylium dyes and its application in dye-sensitized solar cells Download PDFInfo
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- CN108359266B CN108359266B CN201810177737.9A CN201810177737A CN108359266B CN 108359266 B CN108359266 B CN 108359266B CN 201810177737 A CN201810177737 A CN 201810177737A CN 108359266 B CN108359266 B CN 108359266B
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- dye
- dithieno
- dibenzo
- solar cells
- sensitized solar
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- 239000000975 dye Substances 0.000 title claims abstract description 65
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 238000004873 anchoring Methods 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical group OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 11
- 239000011521 glass Substances 0.000 claims description 10
- 239000000758 substrate Substances 0.000 claims description 6
- SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical compound [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 206010070834 Sensitisation Diseases 0.000 claims description 4
- 230000008313 sensitization Effects 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- OBISXEJSEGNNKL-UHFFFAOYSA-N dinitrogen-n-sulfide Chemical compound [N-]=[N+]=S OBISXEJSEGNNKL-UHFFFAOYSA-N 0.000 claims description 3
- 230000005611 electricity Effects 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 2
- 239000012964 benzotriazole Substances 0.000 claims description 2
- 238000003287 bathing Methods 0.000 claims 1
- 238000007654 immersion Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 12
- 150000003233 pyrroles Chemical class 0.000 abstract description 8
- 238000000862 absorption spectrum Methods 0.000 abstract description 5
- 230000008033 biological extinction Effects 0.000 abstract description 5
- 230000004044 response Effects 0.000 abstract description 5
- 230000003287 optical effect Effects 0.000 abstract description 3
- BKYWEUVIGUEMFX-UHFFFAOYSA-N 4h-dithieno[3,2-a:2',3'-d]pyrrole Chemical group S1C=CC2=C1NC1=C2SC=C1 BKYWEUVIGUEMFX-UHFFFAOYSA-N 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 230000021615 conjugation Effects 0.000 abstract description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical class C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052751 metal Inorganic materials 0.000 abstract description 2
- 239000002184 metal Substances 0.000 abstract description 2
- 230000003595 spectral effect Effects 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical class ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 239000008367 deionised water Substances 0.000 description 7
- 229910021641 deionized water Inorganic materials 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000008151 electrolyte solution Substances 0.000 description 4
- 239000002159 nanocrystal Substances 0.000 description 4
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- 238000010792 warming Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- 230000002459 sustained effect Effects 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 229910000160 potassium phosphate Inorganic materials 0.000 description 2
- 235000011009 potassium phosphates Nutrition 0.000 description 2
- 230000001235 sensitizing effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- OTEKOJQFKOIXMU-UHFFFAOYSA-N 1,4-bis(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=C(C(Cl)(Cl)Cl)C=C1 OTEKOJQFKOIXMU-UHFFFAOYSA-N 0.000 description 1
- -1 2- hexyl decyl Chemical group 0.000 description 1
- ZZPNDIHOQDQVNU-UHFFFAOYSA-N 2-hydroxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound CC1(C)OB(O)OC1(C)C ZZPNDIHOQDQVNU-UHFFFAOYSA-N 0.000 description 1
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- 101150090068 PMII gene Proteins 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- PAMBVPQLDDXPCQ-UHFFFAOYSA-N boric acid;n,n-diphenylaniline Chemical compound OB(O)O.C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 PAMBVPQLDDXPCQ-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- XAXHEVRKPSEDKX-UHFFFAOYSA-N cyanic acid;guanidine Chemical compound [O-]C#N.NC([NH3+])=N XAXHEVRKPSEDKX-UHFFFAOYSA-N 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 239000002803 fossil fuel Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002678 macrocyclic compounds Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- WYURNTSHIVDZCO-SVYQBANQSA-N oxolane-d8 Chemical compound [2H]C1([2H])OC([2H])([2H])C([2H])([2H])C1([2H])[2H] WYURNTSHIVDZCO-SVYQBANQSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000005622 photoelectricity Effects 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 238000010248 power generation Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- RBNWAMSGVWEHFP-UHFFFAOYSA-N trans-p-Menthane-1,8-diol Chemical compound CC(C)(O)C1CCC(C)(O)CC1 RBNWAMSGVWEHFP-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/0008—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain
- C09B23/005—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain the substituent being a COOH and/or a functional derivative thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/0008—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain
- C09B23/005—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain the substituent being a COOH and/or a functional derivative thereof
- C09B23/0058—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain the substituent being a COOH and/or a functional derivative thereof the substituent being CN
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/008—Triarylamine dyes containing no other chromophores
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- 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
- H01G9/2027—Light-sensitive devices comprising an oxide semiconductor electrode
- H01G9/2031—Light-sensitive devices comprising an oxide semiconductor electrode comprising titanium oxide, e.g. TiO2
-
- 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
- H01G9/2059—Light-sensitive devices comprising an organic dye as the active light absorbing material, e.g. adsorbed on an electrode or dissolved in solution
-
- 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
-
- 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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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Power Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Hybrid Cells (AREA)
- Photovoltaic Devices (AREA)
Abstract
Application the invention discloses dibenzo dithieno pyrylium dyes and its in dye-sensitized solar cells.Dyestuff based on dibenzo dithieno pyrroles of the invention is the pure organic photosensitive dyestuff without metal, wherein, using trianilino group as electron donor, dibenzothiophenes and the big conjugation group of pyrroles are introduced in π bridge, using cyanoacetic acid group as electron acceptor and anchoring group, and branched alkyl chain is introduced on dibenzo dithieno pyrrole group, effectively increase the conjugate area of dibenzo dithieno pyrylium dyes molecule, with larger space steric hindrance, expand spectral response and effectively widens absorption spectrum, improve molar extinction coefficient, with preferably catching optical property and good inhibit the compound ability of electronics, it is applied in dye-sensitized solar cells as sensitizer, to improve the photoelectric conversion efficiency of dye-sensitized solar cells.
Description
Technical field
The present invention relates to organic dyestuff technical fields, and in particular to the sensitizing dyestuff of dye-sensitized solar cells and its answers
With.
Background technique
The problems such as a large amount of with traditional fossil energy consume and use, energy crisis, greenhouse effects, environmental pollution becomes
Realize the serious hindrance of economic, society, resource and environmental protection etc. coordinated development in countries in the world.Find clean renewable new energy
Source substitutes traditional fossil energy, becomes the key that the whole world solves the problems, such as this.Solar energy is the most abundant as a kind of deposit
The energy, inexhaustible, nexhaustible compared with fossil fuel, when use, does not destroy earth thermal balance and is conducive to ecological protection；
It is considered as most direct and most effective approach, dye-sensitized solar cells using solar energy that solar cell, which carries out photovoltaic power generation,
(DSSCs) be then photovoltaic industry one of representative, since its preparation process is simple, manufacturing cost is cheap, becomes the sun in recent years
The research hotspot in energy photoelectric conversion field.
Wherein, the pure organic dye based on dithieno pyrroles's Conjugate macrocycle has excellent light ability of catching, and high mole disappears
Backscatter extinction logarithmic ratio, broader light abstraction width, and there is excellent spectrochemical property and good photostability, chemical stability,
There is good application in dye-sensitized solar cells.On this basis, by each side introducing one in dithieno pyrroles
A dibenzo dithieno pyrroles for being conjugated phenyl ring and generating can increase conjugate area on the basis of original, widen extinction model
It encloses, realizes the more fully absorption to light.Up to the present there are no the pure organic dyes based on dibenzo dithieno pyrroles
Report.The present invention designs and synthesizes one kind using triphenylamine as electron donor, and dibenzo dithieno pyrroles is π bridge, cyano second
Acid is the pure organic dye of electron acceptor and anchoring group.The dyestuff has structure simple, and synthesis is easy, and photoelectric conversion performance is good
The advantages that good.
Summary of the invention
In view of the above-mentioned deficiencies in the prior art, it is an object of the present invention to provide a kind of dibenzo dithieno pyrylium dyes.
Dibenzo dithieno pyrylium dyes of the invention be the pure organic photosensitive dyestuff without metal, wherein with trianilino group be electricity
Sub- donor, introduces dibenzothiophenes and the big conjugation group of pyrroles in π bridge, and cyanoacetic acid group is electron acceptor and anchoring base
Group.
Dibenzo dithieno pyrylium dyes synthesis technology of the invention is simple, and raw material is cheap and easy to get, can be carried out scale
Production.
Another object of the present invention, which also resides in, provides a kind of dibenzo dithieno pyrylium dyes in dye sensitization
Application in battery.The dibenzo dithieno pyrylium dyes are applied in dye-sensitized solar cells as sensitizer, so that
Dye-sensitized solar cells have good photoelectric properties.
The purpose of the present invention is achieved through the following technical solutions.
A kind of dibenzo dithieno pyrylium dyes, chemical structural formula are as follows:
In formula, R1、R2It is independently chosen from hydrogen atom, C1~C20Straight chained alkyl or C1~C20Alkoxy；R3Selected from C1~
C20Branched alkyl；A1For diazosulfide or benzotriazole；
Wherein, cyanoacetic acid group is as electron acceptor and anchoring group.
A kind of application of dibenzo dithieno pyrylium dyes described above in dye-sensitized solar cells, will be described
Dibenzo dithieno pyrylium dyes are applied in dye-sensitized solar cells as sensitizer, specifically: nanometer two will be loaded
The electro-conductive glass substrate of titanium oxide is immersed in the dye bath solution of dibenzo dithieno pyrylium dyes preparation, hexichol 1,4-Dithiapentalene
And pyrylium dyes are adsorbed on nano-titanium dioxide surface by anchoring group, are prepared into the work electricity of dye-sensitized solar cells
Pole.
Further, the solvent of the dye bath solution is tetrahydrofuran.
Further, the concentration of the dye bath solution is 2~5 × 10-4mol·L-1。
Further, described impregnate is impregnated 12~24 hours in dark light protected environment.
Compared with prior art, the invention has the advantages that and the utility model has the advantages that
Dibenzo dithieno pyrylium dyes of the invention introduce dibenzo dithieno pyrrole group in π bridge, effectively
Increase the conjugate area of dibenzo dithieno pyrylium dyes molecule, there is larger space steric hindrance, expansion spectral response is simultaneously effective
Absorption spectrum is widened, molar extinction coefficient is improved, has and preferably catches optical property and the good ability for inhibiting electronics compound,
It is applied in dye-sensitized solar cells as sensitizer, to improve the photoelectric conversion efficiency of dye-sensitized solar cells.
Detailed description of the invention
Fig. 1 is the ultraviolet/visible absorption spectra figure of the dyestuff WL that synthesizes in tetrahydrofuran in embodiment 1；
Fig. 2 is the J-V curve for the dye-sensitized solar cells that the dyestuff WL synthesized in embodiment 1 makes as sensitizer
Figure.
Specific embodiment
Technical solution of the present invention is described in further detail below in conjunction with specific embodiments and drawings, but of the invention
Protection scope and embodiment are without being limited thereto.
Embodiment 1
Dibenzo dithieno pyrylium dyes WL (R1、R2It is hydrogen atom, R3For 2- hexyl decyl, A1For benzo thiophene two
Azoles) synthesis, synthetic route is as follows:
Specific synthesis step is as follows:
(1) synthesis of compound 2
In the two-mouth bottle of 50mL be added compound 1 (150mg, 0.22mmol), triphenylamine borate (74.2mg,
0.22mmol), the aqueous potassium phosphate solution (0.22mL) and Pd (PPh of 2M3)4(23mg, 0.22mmol) then adds 30mL's
The ethyl alcohol of toluene and 5mL；It is evacuated with vacuum pump, then blasts N2, operate repeatedly three times；Then oil bath is warming up to 90
DEG C, sustained response 24 hours；To after reaction, cool the temperature to room temperature, then reaction solution is poured into water, with 100mL bis-
Chloromethanes extraction, is then washed twice with 200mL water again, and with the dry organic phase of anhydrous magnesium sulfate, filtering removes solvent, slightly
Product chromatographs to separate using column, and mobile phase is petroleum ether and methylene chloride (v/v=5: 1), obtains the solid product of yellow
116mg, yield 64%.Fusing point is 82~85 DEG C.1H NMR (400MHz, CDCl3) δ 7.98-7.96 (m, 1H), 7.87-7.86
(m, 1H), 7.66-7.63 (m, 1H), 7.59-7.57 (m, 2H), 7.53-7.51 (m, 1H) 7.48-7.46 (m, 1H), 7.40-
7.38 (m, 1H), 7.36-7.30 (m, 4H), 7.25-7.20 (m, 6H), 7.12-7.08 (m, 2H), 4.16 (d, J=7.7Hz,
2H), 2.08-1.98 (m, 1H), 1.32-1.15 (m, 24H), 0.92-0.84 (m, 6H)
(2) synthesis of compound 3
In the two-mouth bottle of 100mL be added compound 2 (280mg, 0.34mmol), connection boric acid pinacol ester (172mg,
0.68mmol)、Pd(dppf)Cl250mL weight is then added in (25mg, 0.034mmol) and potassium acetate (132mg, 0.68mmol)
Isosorbide-5-Nitrae-dioxane of steaming；It is evacuated with vacuum pump, then blasts N2, operate repeatedly three times；Then oil bath is warming up to 105
DEG C, sustained response 16 hours；To after reaction, cool the temperature to room temperature, then reaction solution is poured into water, with 100mL bis-
Chloromethanes extraction, then uses 200mL water washing twice again, and with the dry organic phase of anhydrous magnesium sulfate, filtering removes solvent, thick production
Object chromatographs to separate using column, and mobile phase is petroleum ether and methylene chloride (v/v=5: 1), obtains crude yellow solid
180mg；
By obtained yellow solid product and the bromo- 5- thiophene cyanoacetic acid tert-butyl ester diazosulfide of 2- (224mg,
It 0.50mmol) is added in the two-mouth bottle of 100mL, adds Pd (PPh3)4The potassium phosphate of (46mg, 0.04mmol) and 2M are water-soluble
Liquid (0.22mL), adds the toluene of 30mL and the ethyl alcohol of 5mL；It is evacuated with vacuum pump, blasts N2, operate repeatedly three times；
Oil bath is warming up to 90 DEG C, sustained response 24 hours；To cool the temperature to room temperature after reaction, reaction solution is poured into water,
It is extracted with 100mL methylene chloride, then washed twice with 200mL water, with the dry organic phase of anhydrous magnesium sulfate, filtering is removed molten
Agent, crude product chromatograph to separate using column, and mobile phase is petroleum ether, methylene chloride and ethyl acetate (v/v/v=20: 1: 1), is obtained
To wine-colored solid product 262mg, yield 50%.Fusing point is 168~171 DEG C.1H NMR (400MHz, CDCl3)δ8.48
(s, 1H), 8.18-8.17 (m, 2H), 8.16-8.15 (m, 1H), 8.05-8.05 (m, 1H), 7.96-7.94 (m, 1H), 7.90-
7.88 (m, 1H), 7.80-7.74 (m, 3H), 7.72-7.70 (m, 1H), 7.58-7.53 (m, 3H), 7.33-7.28 (m, 4H),
7.20-7.17 (m, 6H), 7.09-7.06 (m, 2H), 4.52 (d, J=7.7Hz, 2H), 2.25-2.15 (m, 1H), 1.61 (s,
9H), 1.45-1.17 (m, 24H), 0.86-0.81 (m, 6H) ..
(3) synthesis of dyestuff WL
Compound 3 (100mg, 0.089mmol) is added in single-necked flask, the trifluoroacetic acid of 15mL is added, at room temperature
Stirring 3h after the reaction was completed pours into reaction solution in 50mL deionized water, and solid will be precipitated and be collected by filtration, then use
300mL deionized water cleaning solid to cleaning solution is in neutrality, and is finally dried in vacuo violet solid dyestuff WL (89mg), yield is
95%, fusing point is 228~231 DEG C.1H NMR (400MHz, THF-d8) δ 10.81 (s, 1H), 8.61 (s, 1H), 8.19-8.14
(m, 3H), 8.03 (s, 1H), 7.94-7.89 (m, 1H), 7.84-7.82 (m, 1H), 7.79-7.72 (m, 3H), 7.63-7.61
(m, 2H), 7.56-7.53 (m, 1H), 7.28-7.24 (m, 4H), 7.13-7.10 (m, 6H), 7.03-7.00 (m, 2H), 4.54
(d, J=7.2Hz, 2H), 2.23-2.12 (m, 1H), 1.43-1.15 (d, J=55.1Hz, 24H), 0.83-0.78 (m, 6H)
Embodiment 2
Ultraviolet-ray visible absorbing optical tests (2 × 10 are carried out to dyestuff WL prepared by embodiment 1-5M tetrahydrofuran solution, room
Temperature), the uv-visible absorption spectra that measures as shown in Figure 1, data summarization in table 1.
The uv-visible absorption spectra data of 1 WL dyestuff of table
From Fig. 1 and table 1 as can be seen that in tetrahydrofuran solution, dyestuff WL shows two significant absorption peaks,
The absorption peak generated at 330nm~430nm for dye molecule electronics π-π * electron transition；For in dye molecule at 430~600nm
Caused by electric charge transfer, the peak a length of 507nm of corresponding maximum absorption wave；Molar extinction coefficient is 39840M-1cm-1, this shows
Dyestuff WL has catches light ability well.
Embodiment 3
The preparation of dye-sensitized solar cells
Dyestuff WL prepared by embodiment 1 is used in dye-sensitized solar cells as sensitizer, preparation is based on dyestuff WL
The dye-sensitized solar cells of sensitizer.
Dye-sensitized solar cells are mainly by electro-conductive glass matrix (FTO), light anode, sensitizer, electrolyte solution and platinum
To electrode (also referred to as photocathode, Pt electro-conductive glass) five big component parts；Wherein, the substrate conducting glass surface of light anode, which is covered with, receives
Meter Duo Kong TiO2Film, to adsorb dyestuff；Platinum is coated with Pt catalyst to the substrate of electrode；Light anode and photocathode relative spacing
Setting, nanoporous TiO2Film periphery is sealed to form closed cavity with sealing material, and electrolyte solution is filled in cavity
With sensitizer (i.e. dibenzo dithieno pyrylium dyes).
The specific preparation process of dye-sensitized solar cells includes the following steps:
(1) pretreatment of electro-conductive glass (FTO): FTO electro-conductive glass being cut, is cleaned by ultrasonic with deionized water, is impregnated
The 20h in the saturation ethanol solution of KOH, then acetone, deionized water ultrasonic cleaning are successively spent, it is dried for standby；
(2) preparation of light anode: at room temperature, first by 10mL Ti (OBu)4Mixing with 20mL EtOH is simultaneously vigorously stirred
10min is then added 30mL acetic acid and 50mL deionized water and continues to stir 1h, then moves into autoclave in 230 DEG C of processing 12h
Afterwards, cooled to room temperature, filtering, and solid is cleaned with deionized water and ethyl alcohol, after drying 6h in baking oven at 50 DEG C, obtain
TiO2Nano-crystal particle；
Take the TiO that 2.0g is prepared2Nano-crystal particle, be separately added into 0.4mL acetic acid, 16.0mL ethyl alcohol, 6.0g terpinol with
And 1g ethyl cellulose, it is fully ground 1h, obtains slurry material, through ultrasound, obtains white sticky TiO2Nano-crystal slurry；
The electro-conductive glass FTO handled well is placed in immediately below silk screen plate in the face-up mode of conducting surface, controls 1cm's
Net is away from the TiO that will be prepared2Nano-crystal slurry, which is placed on silk screen, to be printed, and TiO is regulated and controled2Film thickness be 17 μm (area is 4 ×
4mm), the electro-conductive glass substrate of load nano-titanium dioxide is obtained；
The electro-conductive glass substrate of the load nano-titanium dioxide of preparation is put into baking oven, it is 5 minutes dry in 125 DEG C, then put
In Muffle furnace, in 325 DEG C of baking 5min, then at 375 DEG C of baking 5min, then at 450 DEG C of baking 15min, finally dried in 500 DEG C
15min is roasted, high-temperature process sufficiently removes the organic substance in light anode；Then it is soaked in the TiCl of 0.2M4It is handled in aqueous solution
Half an hour, after treatment are rinsed well with deionized water and ethyl alcohol, are placed in Muffle furnace, are warming up to 500 DEG C and are baked again
30min obtains light anode, is placed in drier after cooling, spare；
(3) preparation of dye solution: dibenzo dithieno pyrylium dyes WL is dissolved in tetrahydrofuran solvent, is configured to
2×10-4mol.L-1Dye solution；
(4) methyl of 1- containing 0.6M -3- propyl iodate imidazoles (PMII), 0.05M sulphur the preparation of electrolyte solution: are prepared
Cyanic acid guanidine, 0.05M LiI, 0.05MI2With the acetonitrile solution of 0.25M tert .-butylpyridine (TBP)；
(5) sensitization of light anode: light anode prepared by step (2) being soaked in the dye solution that dye step (3) is prepared,
It in dark light protected environment after dye bath 24 hours, takes out, and rinses surface with alcohol solvent, remove residual or physical absorption in film
The dyestuff on surface, after drying, the dry light protected environment of preservation is spare with to be packaged；
(6) light anode prepared is covered with the ambroin film having had openning hole, and to the light anode covered
The electrolyte solution that part drop upper 1~2 is dripped, and the platinum of preparation is closely covered in light anode to electrode, both sides are fixed with clip
Form open sensitizing dyestuff solar cell to be measured.
Dye-sensitized solar cells performance test:
Extraction wire is distinguished from the light anode and photocathode of the dye-sensitized solar cells of preparation, is connected to battery performance test
On device, the work area of battery is 0.16cm2, with solar simulator simulated solar irradiation, luminous intensity is adjusted to 100mW/
cm2Test the J-V curve of the battery of the dye sensitization based on preparation.
The J-V curve graphs of measured dye-sensitized solar cells as shown in Fig. 2, data summarization in table 2.
2 dyestuff WJ of table is used for dye-sensitized solar cells performance data
It can be seen that the dye-sensitized solar cells that dyestuff WL is sensitized from the data of Fig. 2 and table 2 and show higher photoelectricity
Transfer efficiency possesses good short circuit current and open-circuit voltage, this shows that dyestuff WL is strong with preferable light capture ability and very
Inhibition aggregation ability.
The above embodiment is a preferred embodiment of the present invention, but embodiments of the present invention are not by above-described embodiment
Limitation, other any changes, modifications, substitutions, combinations, simplifications made without departing from the spirit and principles of the present invention,
It should be equivalent substitute mode, be included within the scope of the present invention.
Claims (4)
1. a kind of dibenzo dithieno pyrylium dyes, which is characterized in that chemical structural formula is as follows:
In formula, R1、R2It is independently chosen from hydrogen atom, C1~C20Straight chained alkyl or C1~C20Alkoxy；R3Selected from C1~C20's
Branched alkyl；A1For diazosulfide or benzotriazole；
Wherein, cyanoacetic acid group is as electron acceptor and anchoring group.
2. a kind of application of the dibenzo dithieno pyrylium dyes described in claim 1 in dye-sensitized solar cells,
It is characterized in that, is applied to the dibenzo dithieno pyrylium dyes as sensitizer in dye-sensitized solar cells, specifically
Are as follows: the electro-conductive glass substrate of load nano-titanium dioxide is immersed in the dye bath solution of dibenzo dithieno pyrylium dyes preparation
In, dibenzo dithieno pyrylium dyes are adsorbed on nano-titanium dioxide surface by anchoring group, are prepared into dye sensitization too
The working electrode in positive electricity pond.
3. application according to claim 2, which is characterized in that the solvent of the dye bath solution is tetrahydrofuran；The dye
The concentration for bathing solution is 2~5 × 10-4mol·L-1。
4. application according to claim 2, which is characterized in that the immersion is to impregnate 12~24 in dark light protected environment
Hour.
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| 新型咔唑基染料敏化太阳电池性能研究;彭锦安等;《材料研究与应用》;20101231;第04卷(第04期);第241-244页 |
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