WO2010037857A1 - Novel use of specified carotenoids as light harvesting pigments in dye sensitized solar cells - Google Patents
Novel use of specified carotenoids as light harvesting pigments in dye sensitized solar cells Download PDFInfo
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- WO2010037857A1 WO2010037857A1 PCT/EP2009/062848 EP2009062848W WO2010037857A1 WO 2010037857 A1 WO2010037857 A1 WO 2010037857A1 EP 2009062848 W EP2009062848 W EP 2009062848W WO 2010037857 A1 WO2010037857 A1 WO 2010037857A1
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- alkyl
- group
- carotenoids
- solar cells
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- 235000021466 carotenoid Nutrition 0.000 title claims abstract description 17
- 150000001747 carotenoids Chemical class 0.000 title claims abstract description 17
- 239000000049 pigment Substances 0.000 title claims description 10
- 238000003306 harvesting Methods 0.000 title description 5
- RAFGELQLHMBRHD-VFYVRILKSA-N Bixin Natural products COC(=O)C=CC(=C/C=C/C(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C(=O)O)/C)C RAFGELQLHMBRHD-VFYVRILKSA-N 0.000 claims abstract description 8
- RAFGELQLHMBRHD-UHFFFAOYSA-N alpha-Fuc-(1-2)-beta-Gal-(1-3)-(beta-GlcNAc-(1-6))-GalNAc-ol Natural products COC(=O)C=CC(C)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC(O)=O RAFGELQLHMBRHD-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000001670 anatto Substances 0.000 claims abstract description 8
- 235000012665 annatto Nutrition 0.000 claims abstract description 8
- RAFGELQLHMBRHD-SLEZCNMESA-N bixin Chemical compound COC(=O)\C=C\C(\C)=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C(O)=O RAFGELQLHMBRHD-SLEZCNMESA-N 0.000 claims abstract description 8
- NESPPCWGYRQEJQ-VATUXEBJSA-N (2e,4e,6e,8e,10e,12e,14e,16e,18e,20e,22e,24e)-2,6,10,14,19,23-hexamethyl-25-(2,6,6-trimethylcyclohexen-1-yl)pentacosa-2,4,6,8,10,12,14,16,18,20,22,24-dodecaenoic acid Chemical compound OC(=O)C(/C)=C/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)CCCC1(C)C NESPPCWGYRQEJQ-VATUXEBJSA-N 0.000 claims abstract description 4
- NESPPCWGYRQEJQ-AGUCYFRTSA-N Torularhodin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C=CC=C(/C)C=CC=C(/C)C=CC=C(/C)C(=O)O NESPPCWGYRQEJQ-AGUCYFRTSA-N 0.000 claims abstract description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- -1 alkaline earth metal salts Chemical class 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000001413 amino acids Chemical class 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
- 235000019804 chlorophyll Nutrition 0.000 claims description 2
- 229930002875 chlorophyll Natural products 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- FDSDTBUPSURDBL-LOFNIBRQSA-N canthaxanthin Chemical compound CC=1C(=O)CCC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)C(=O)CCC1(C)C FDSDTBUPSURDBL-LOFNIBRQSA-N 0.000 abstract description 4
- KBPHJBAIARWVSC-XQIHNALSSA-N trans-lutein Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C(=CC(O)CC2(C)C)C KBPHJBAIARWVSC-XQIHNALSSA-N 0.000 abstract description 3
- JKQXZKUSFCKOGQ-JLGXGRJMSA-N (3R,3'R)-beta,beta-carotene-3,3'-diol Chemical compound C([C@H](O)CC=1C)C(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)C[C@@H](O)CC1(C)C JKQXZKUSFCKOGQ-JLGXGRJMSA-N 0.000 abstract description 2
- JEBFVOLFMLUKLF-IFPLVEIFSA-N Astaxanthin Natural products CC(=C/C=C/C(=C/C=C/C1=C(C)C(=O)C(O)CC1(C)C)/C)C=CC=C(/C)C=CC=C(/C)C=CC2=C(C)C(=O)C(O)CC2(C)C JEBFVOLFMLUKLF-IFPLVEIFSA-N 0.000 abstract description 2
- OOUTWVMJGMVRQF-DOYZGLONSA-N Phoenicoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)C(=O)C(O)CC1(C)C)C=CC=C(/C)C=CC2=C(C)C(=O)CCC2(C)C OOUTWVMJGMVRQF-DOYZGLONSA-N 0.000 abstract description 2
- JKQXZKUSFCKOGQ-LQFQNGICSA-N Z-zeaxanthin Natural products C([C@H](O)CC=1C)C(C)(C)C=1C=CC(C)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC1=C(C)C[C@@H](O)CC1(C)C JKQXZKUSFCKOGQ-LQFQNGICSA-N 0.000 abstract description 2
- QOPRSMDTRDMBNK-RNUUUQFGSA-N Zeaxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCC(O)C1(C)C)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C QOPRSMDTRDMBNK-RNUUUQFGSA-N 0.000 abstract description 2
- JKQXZKUSFCKOGQ-LOFNIBRQSA-N all-trans-Zeaxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C JKQXZKUSFCKOGQ-LOFNIBRQSA-N 0.000 abstract description 2
- 235000013793 astaxanthin Nutrition 0.000 abstract description 2
- 239000001168 astaxanthin Substances 0.000 abstract description 2
- MQZIGYBFDRPAKN-ZWAPEEGVSA-N astaxanthin Chemical compound C([C@H](O)C(=O)C=1C)C(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)C(=O)[C@@H](O)CC1(C)C MQZIGYBFDRPAKN-ZWAPEEGVSA-N 0.000 abstract description 2
- 229940022405 astaxanthin Drugs 0.000 abstract description 2
- 235000012682 canthaxanthin Nutrition 0.000 abstract description 2
- 239000001659 canthaxanthin Substances 0.000 abstract description 2
- 229940008033 canthaxanthin Drugs 0.000 abstract description 2
- 235000010930 zeaxanthin Nutrition 0.000 abstract description 2
- 239000001775 zeaxanthin Substances 0.000 abstract description 2
- 229940043269 zeaxanthin Drugs 0.000 abstract description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 3
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 239000004904 UV filter Substances 0.000 description 1
- 235000010208 anthocyanin Nutrition 0.000 description 1
- 239000004410 anthocyanin Substances 0.000 description 1
- 229930002877 anthocyanin Natural products 0.000 description 1
- 150000004636 anthocyanins Chemical class 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 239000008151 electrolyte solution Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000012680 lutein Nutrition 0.000 description 1
- 239000001656 lutein Substances 0.000 description 1
- KBPHJBAIARWVSC-RGZFRNHPSA-N lutein Chemical compound C([C@H](O)CC=1C)C(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\[C@H]1C(C)=C[C@H](O)CC1(C)C KBPHJBAIARWVSC-RGZFRNHPSA-N 0.000 description 1
- 229960005375 lutein Drugs 0.000 description 1
- ORAKUVXRZWMARG-WZLJTJAWSA-N lutein Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C=CC=C(/C)C=CC2C(=CC(O)CC2(C)C)C ORAKUVXRZWMARG-WZLJTJAWSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- FJHBOVDFOQMZRV-XQIHNALSSA-N xanthophyll Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C=C(C)C(O)CC2(C)C FJHBOVDFOQMZRV-XQIHNALSSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- H10K85/652—Cyanine dyes
-
- 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
-
- 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
Definitions
- the present invention relates to a novel use of specific carotenoids; in particular it relates to the use of carotenoids as pigments in dye sensitized solar cells.
- Dye-sensitized solar cells are a relatively new class of low-cost solar cells.
- a well described example is the Graetzel cell.
- a Graetzel cell is a photoelectrochemical system based on a semiconductor (e. g. TiO " 2 ) located between a photo-sensitized anode and an electrolyte (B. O'Regan & M. Graetzel, Nature 353, 737-740, 1991 ; Graetzel et al., United States Patent, No. 5,084,365, 1992; A. Hagefeldt & M. Graetzel, Ace. Chem. Res. 33, 269-277, 2000).
- a semiconductor e. g. TiO " 2
- Lutein and chlorophyll and a combination of both have recently also been shown to function as light harvesting pigments in a Graetzel cell (Liu Bao-Qi, Zhao Xiao-Peng. Acta Photonica Sinica, 35(2), 184-187, 2006).
- the carotenoids according to the present invention are preferably chosen from one or more of the following groups 1 to 4.
- n O, 1 , 2, 3 or 4;
- R1 hydrogen, C 1-16 -alkyl, C 1-16 -alkenyl or C 5 - 8 -cycloalkyl.
- n O or 1 ;
- R is selected from the following residues: -NH-CH(RI )-COOR2, -0R3, -(Y) n -Z with
- R1 H, or the residue of a protein-forming amino acid
- R2 d- 6 -alkyl or C 3-8 -cycloalkyl
- R3 Ci- 16 -alkyl or C 3-8 -cycloalkyl
- Z -NH 2 , -OC(O)R4, -0R4, -COOR4; wherein R4 is selected from H, C- ⁇ - 6 -alkyl, -aryl or -heteroaryl, alkali or alkaline earth metal salts;
- R3, R4 are independently from each other selected from H, a protected OH-group or an oxo-group;
- R5 is the before mentioned residue the other R5 is a protected formyl group, e.g. a cyclic or acyclic acetal.
- R1 , R2 are independently from each other selected from the following residues:
- bixin and/or torularhodin More preferred are bixin and/or torularhodin; Most preferred is bixin.
- Graetzel cells from ManSolar were set up in our laboratory in a standardized device. All carotenoids were dissolved in tetrahydrofuran (THF). THF contained butylated hydroxytoluene (BHT) to protect against peroxides. 10 mM stock solutions of carotenoids in THF/BHT were diluted. 200 ⁇ l of a 10 mM, 1 mM, and 0.1 mM carotenoid solution were directly pipetted onto the TiO 2 layer of the anode and dried under an argon atmosphere. The electrodes (ITO glass) and the electrolyte were from ManSolar
- Graphite was sprayed onto the cathode from a commercial lubricant product.
- the electrodes were assembled with Teflon stripes of 1 mm width at the two borders without electric transfer contacts. The resistance between the contacts and the electrode were > 1 Ohm.
- the solar cell was assembled, electrolyte solution was injected into the spaces of the electrodes and the solar cell was placed into the cell holder. Sun light was simulated with a 150 W Xenophot HLX lamp in 1 m distance. The temperature was controlled by a Peltron control unit.
- the solar cells were connected to a labview-based device with which the voltage on the cell was regulated and the current was measured. The power was calculated from the IV curves.
- the light conversion efficacy calculation ( ⁇ ) was performed in the following way:
- the fill factor is a key parameter in evaluating the performance of solar cells.
- Bixin showed the maximal light conversion efficiency ⁇ .
- Figure 1 shows an efficiency ( ⁇ ) versus time plot of 10 mM Bixin in comparison to the solvent THF.
Landscapes
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Power Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Hybrid Cells (AREA)
Abstract
Use of specific carotenoids in dye sensitized solar cells. Preferred carotenoids according to the present invention are listed in the following : Bixin (A), Canthaxanthin (B), Astaxanthin (C), Zeaxanthin (D), Torularhodin (E).
Description
Novel use of specified carotenoids as light harvesting pigments in dye sensitized solar cells
The present invention relates to a novel use of specific carotenoids; in particular it relates to the use of carotenoids as pigments in dye sensitized solar cells.
Dye-sensitized solar cells are a relatively new class of low-cost solar cells. A well described example is the Graetzel cell. A Graetzel cell is a photoelectrochemical system based on a semiconductor (e. g. TiO" 2) located between a photo-sensitized anode and an electrolyte (B. O'Regan & M. Graetzel, Nature 353, 737-740, 1991 ; Graetzel et al., United States Patent, No. 5,084,365, 1992; A. Hagefeldt & M. Graetzel, Ace. Chem. Res. 33, 269-277, 2000). A wide variety of organic dyes based on porphyrines and chlorophyll derivatives (A. Kay & M. Graetzel, J. Phys. Chem. 97, 6272-6277, 1993) and anthocyanins (NJ. Cherepy et al., J. Phsy. Chem. 101 , 9342- 9351 , 1997; A.S. Polo & N. Y. Murakami-lha, Solar Energy Material & Solar Cells 90, 1936-1944, 2006) have been used as light harvesting pigments.
Lutein and chlorophyll and a combination of both have recently also been shown to function as light harvesting pigments in a Graetzel cell (Liu Bao-Qi, Zhao Xiao-Peng. Acta Photonica Sinica, 35(2), 184-187, 2006).
But there is still a need for light harvesting pigments that may be used in dye sensitized solar cells. It was therefore an object of the present invention to provide ingredients having the desired properties as indicated above.
This objective has been solved by the carotenoids according to the present invention.
The carotenoids according to the present invention (one or more compounds) are preferably chosen from one or more of the following groups 1 to 4.
Group 1 : Asymmetric carotenoids of the structure
wherein
• A1, A2 are independently from each other selected from the following residues: -H, OH, =0, -OC(O)RI ;
• n = O, 1 , 2, 3 or 4;
• o = 1 or 2; and
• R is selected from the following residues:
R1 = hydrogen, C1-16-alkyl, C1-16-alkenyl or C5-8-cycloalkyl.
Group 2: Symmetric C30- and C40-carotenoids of the structure
wherein
• A1, A2 are independently from each other selected from the following residues: -H, - OH, =0, -OC(O)R;
• B1 = H, B2 = H, OH, -OC(O)R or B1 and B2 together build =0;
• n = O or 1 ;
• R is selected from the following residues: -NH-CH(RI )-COOR2, -0R3, -(Y)n-Z with
R1 = H, or the residue of a protein-forming amino acid;
R2 = d-6-alkyl or C3-8-cycloalkyl;
R3 = Ci-16-alkyl or C3-8-cycloalkyl;
Y = d-7-alkylene or C2-7-alkenylene; n = O or 1
Z = -NH2, -OC(O)R4, -0R4, -COOR4; wherein R4 is selected from H, C-ι-6-alkyl, -aryl or -heteroaryl, alkali or alkaline earth metal salts;
Group 3: Hydroxy ketones with one of the structures I to
• m = 0, 1 , 2, 3 or 4
• n = 0 or 1 • p = 0, 1 or 2
• q = 0, 1 , 2 or 3
• r = 0, 1 or 2
• s = 1 or 2
• R is selected from H, alkyl, acyl; • R1 is Ci _ 6-alkyl; R2 = is C1 _ 6-alkyl or C2-6-alkenyl or R1 and R2 together build 1 ,4- tetramethylene or 1 ,5-pentamethylene;
• R3, R4 are independently from each other selected from H, a protected OH-group or an oxo-group; and
• either one or both R5 are o
,R1 "OH R2 , whereas in case only one R5 is the before mentioned residue the other R5 is a protected formyl group, e.g. a cyclic or acyclic acetal.
Group 4: Symmetric and asymmetric open chain carotenoids of the structure
• n = 0, 1 or 2; • m = 0 or 1 ;
• o = 0, 1 or 2; and
• R1 , R2 are independently from each other selected from the following residues:
-C(O)CH3, -CHO, -C(O)OR3, -C(O)CHO,
with R3 = H, branched or linear Ci^o-alkyl.
Preferred carotenoids according to the present invention are listed in the following:
Bixin
Canthaxanthin
More preferred are bixin and/or torularhodin; Most preferred is bixin.
The present invention is further illustrated by the following example, which is not intended to be limiting.
Examples:
Example 1
Graetzel cells from ManSolar were set up in our laboratory in a standardized device. All carotenoids were dissolved in tetrahydrofuran (THF). THF contained butylated hydroxytoluene (BHT) to protect against peroxides. 10 mM stock solutions of carotenoids in THF/BHT were diluted. 200 μl of a 10 mM, 1 mM, and 0.1 mM carotenoid solution were directly pipetted onto the TiO2 layer of the anode and dried under an argon atmosphere. The electrodes (ITO glass) and the electrolyte were from ManSolar
(www.mansoiar.com). Graphite was sprayed onto the cathode from a commercial lubricant product. The electrodes were assembled with Teflon stripes of 1 mm width at the two borders without electric transfer contacts. The resistance between the contacts and the electrode were > 1 Ohm. The solar cell was assembled, electrolyte solution was injected into the spaces of the electrodes and the solar cell was placed into the cell holder. Sun light was simulated with a 150 W Xenophot HLX lamp in 1 m distance. The temperature was controlled by a Peltron control unit. The solar cells were connected to a labview-based device with which the voltage on the cell was regulated and the current was measured. The power was calculated from the IV curves.
The light conversion efficacy calculation (η) was performed in the following way: The surface area used in the solar station to measure the energy of simulated sun light was F = π r2 = π (0.45)2 cm2 = 0.64 cm2. The energy measured with UV filter was 70 mW / 0.64 cm2 = 110 mW / cm2. The TiO2 surface area of a solar cell (ManSolar) was 1.9 cm x 3 cm = 5.7 cm2. Therefore, the energy input was 110 mW / cm2 x 5.7 cm2 = 627 mW. The fill factor is a key parameter in evaluating the performance of solar cells. It is defined as the ratio of the actual maximum obtainable power (lmp x Vmp) to the theoretical power (lSc x VOc)- Lp and Vmp represent the current density and voltage at the maximum power point. This point is being obtained by varying the resistance in the circuit until I x V is at its greatest value.
Results
The following results were obtained by measuring carotenoids in THF the solar cells under defined conditions (Table 1 ):
Table 1 :
Bixin showed the maximal light conversion efficiency η.
Figure 1 shows an efficiency (η) versus time plot of 10 mM Bixin in comparison to the solvent THF.
Claims
1. Use of one or more compounds from the following groups 1 to 4 as pigments in dye sensitized solar cells:
Group 1 : Asymmetric carotenoids of the structure
wherein
• A1, A2 are independently from each other selected from the following residues: H1 -OH1 =O, -OC(O)RI ;
• n = 0, 1 , 2, 3 or 4;
• o = 1 or 2; and
• R is selected from the following residues:
R1 = hydrogen, Ci-i6-alkyl, Ci-i6-alkenyl or Cs-s-cycloalkyl.
wherein
• A1, A2 are independently from each other selected from the following residues: H, -OH, =0, -OC(O)R;
• B1 = H, B2 = H, OH, -OC(O)R or B1 and B2 together build =0; • n = 0 or 1 ;
• R is selected from the following residues: -NH-CH(RI )-COOR2, -0R3, -(Y)n-Z with
R1 = H, or the residue of a protein-forming amino acid;
R2 = d-6-alkyl or C3-8-cycloalkyl; R3 = Ci-16-alkyl or C3-8-cycloalkyl;
Y = d-7-alkylene or C2-7-alkenylene; n = O or 1
Z = -NH2, -OC(O)R4, -0R4, -COOR4; wherein R4 is selected from H, C1-6-alkyl, -aryl or -heteroaryl, alkali or alkaline earth metal salts;
Group 3: Hydroxy ketones with one of the structures I to III:
wherein
• m = 0, 1 , 2, 3 or 4
• n = 0 or 1
• p = 0, 1 or 2
• q = 0, 1 , 2 or 3
• r = 0, 1 or 2
• s = 1 or 2
• R is selected from H, alkyl, acyl;
• R1 is Ci -6-alkyl; R2 = is Ci _6-alkyl or C2-6-alkenyl or R1 and R2 together build 1 ,4-tetramethylene or 1 ,5-pentamethylene;
• R3, R4 are independently from each other selected from H, a protected OH- group or an oxo-group; and
• either one or both R5 are
whereas in case only one R5 is the before mentioned residue the other R5 is a protected formyl group, e.g. a cyclic or acyclic acetal.
• n = 0, 1 or 2;
• m = 0 or 1 ;
• o = 0, 1 or 2; and
• R1 , R2 are independently from each other selected from the following residues:
2. Use according to claim 1 wherein bixin and/or torularhodin are chosen as pigment(s).
3. Use according to claim 1 wherein the pigment is bixin.
4. Use according to one of the claims 1 to 3 wherein the (one or more) pigment(s) are used in combination with (one or more) chlorophyll(s).
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WO2014122315A1 (en) * | 2013-02-11 | 2014-08-14 | Dsm Ip Assets B.V. | Increase of light conversion efficiency in dye-sensitized solar cells by natural photosensitizers and combination thereof |
CN111430539A (en) * | 2020-03-16 | 2020-07-17 | 电子科技大学 | Long-life electronic skin and preparation method thereof |
CN111430547A (en) * | 2020-03-19 | 2020-07-17 | 电子科技大学 | Organic solar cell based on astaxanthin cathode buffer layer and preparation method thereof |
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CN111430539A (en) * | 2020-03-16 | 2020-07-17 | 电子科技大学 | Long-life electronic skin and preparation method thereof |
CN111430545A (en) * | 2020-03-16 | 2020-07-17 | 电子科技大学 | Organic solar cell based on astaxanthin additive and preparation method thereof |
CN111430547A (en) * | 2020-03-19 | 2020-07-17 | 电子科技大学 | Organic solar cell based on astaxanthin cathode buffer layer and preparation method thereof |
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