JP2002512729A - 金属複合体光増感剤および光起電力セル - Google Patents
金属複合体光増感剤および光起電力セルInfo
- Publication number
- JP2002512729A JP2002512729A JP54787198A JP54787198A JP2002512729A JP 2002512729 A JP2002512729 A JP 2002512729A JP 54787198 A JP54787198 A JP 54787198A JP 54787198 A JP54787198 A JP 54787198A JP 2002512729 A JP2002512729 A JP 2002512729A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- phenyl
- complex
- cooh
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000003504 photosensitizing agent Substances 0.000 title claims abstract description 48
- 239000002905 metal composite material Substances 0.000 title description 3
- 239000003446 ligand Substances 0.000 claims abstract description 63
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 48
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims abstract description 40
- 229910052762 osmium Inorganic materials 0.000 claims abstract description 27
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical group [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims abstract description 27
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims abstract description 26
- 229910052707 ruthenium Inorganic materials 0.000 claims abstract description 26
- 239000004408 titanium dioxide Substances 0.000 claims abstract description 19
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229910052723 transition metal Chemical group 0.000 claims abstract description 14
- 150000003624 transition metals Chemical group 0.000 claims abstract description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 11
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 11
- 229910052742 iron Inorganic materials 0.000 claims abstract description 7
- 229910052702 rhenium Inorganic materials 0.000 claims abstract description 7
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical group [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052713 technetium Inorganic materials 0.000 claims abstract description 7
- GKLVYJBZJHMRIY-UHFFFAOYSA-N technetium atom Chemical compound [Tc] GKLVYJBZJHMRIY-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 54
- YCIMNLLNPGFGHC-UHFFFAOYSA-N pyrocatechyl group Chemical group C=1(O)C(O)=CC=CC1 YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 16
- -1 Phenyl Chemical group 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 10
- 150000003141 primary amines Chemical class 0.000 claims description 10
- 150000003335 secondary amines Chemical class 0.000 claims description 10
- 150000003512 tertiary amines Chemical class 0.000 claims description 10
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 5
- 239000002253 acid Substances 0.000 abstract description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract 2
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 abstract 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229930192474 thiophene Natural products 0.000 abstract 1
- 150000003852 triazoles Chemical class 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 52
- 238000000034 method Methods 0.000 description 48
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 40
- 238000012546 transfer Methods 0.000 description 34
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 25
- 238000000862 absorption spectrum Methods 0.000 description 24
- 239000002131 composite material Substances 0.000 description 22
- 239000000243 solution Substances 0.000 description 19
- 239000011521 glass Substances 0.000 description 16
- 239000002184 metal Substances 0.000 description 14
- NBPGPQJFYXNFKN-UHFFFAOYSA-N 4-methyl-2-(4-methylpyridin-2-yl)pyridine Chemical compound CC1=CC=NC(C=2N=CC=C(C)C=2)=C1 NBPGPQJFYXNFKN-UHFFFAOYSA-N 0.000 description 13
- 229910052751 metal Inorganic materials 0.000 description 13
- 125000004093 cyano group Chemical group *C#N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- YAYGSLOSTXKUBW-UHFFFAOYSA-N ruthenium(2+) Chemical compound [Ru+2] YAYGSLOSTXKUBW-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 9
- 238000001720 action spectrum Methods 0.000 description 7
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000004873 anchoring Methods 0.000 description 6
- 239000012528 membrane Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 230000003595 spectral effect Effects 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- 239000010936 titanium Substances 0.000 description 6
- HQHIWHRZWSFFGP-UHFFFAOYSA-N 4-methyl-2-(4-methylpyridin-2-yl)pyridine;ruthenium Chemical compound [Ru].CC1=CC=NC(C=2N=CC=C(C)C=2)=C1 HQHIWHRZWSFFGP-UHFFFAOYSA-N 0.000 description 5
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- KYBXRGMGABIYAW-UHFFFAOYSA-N 4-methyl-2-(4-methylpyridin-2-yl)pyridine;osmium Chemical compound [Os].CC1=CC=NC(C=2N=CC=C(C)C=2)=C1 KYBXRGMGABIYAW-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000000084 colloidal system Substances 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000012327 Ruthenium complex Substances 0.000 description 3
- 206010070834 Sensitisation Diseases 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 150000003303 ruthenium Chemical class 0.000 description 3
- 230000008313 sensitization Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- JFJNVIPVOCESGZ-UHFFFAOYSA-N 2,3-dipyridin-2-ylpyridine Chemical compound N1=CC=CC=C1C1=CC=CN=C1C1=CC=CC=N1 JFJNVIPVOCESGZ-UHFFFAOYSA-N 0.000 description 2
- INWFLBXPENDFJW-UHFFFAOYSA-N 3,4-dimethyl-2-pyridin-2-ylpyridine Chemical compound CC1=CC=NC(C=2N=CC=CC=2)=C1C INWFLBXPENDFJW-UHFFFAOYSA-N 0.000 description 2
- HEALSPFCFYXUNT-UHFFFAOYSA-N 4,4-dimethyl-2-pyridin-2-yl-3h-pyridine Chemical group C1=CC(C)(C)CC(C=2N=CC=CC=2)=N1 HEALSPFCFYXUNT-UHFFFAOYSA-N 0.000 description 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000004472 Lysine Substances 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 239000003570 air Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000000451 chemical ionisation Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 238000001493 electron microscopy Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010304 firing Methods 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- ISHFYECQSXFODS-UHFFFAOYSA-M 1,2-dimethyl-3-propylimidazol-1-ium;iodide Chemical compound [I-].CCCN1C=C[N+](C)=C1C ISHFYECQSXFODS-UHFFFAOYSA-M 0.000 description 1
- ZZTDEFHCSZAWMD-UHFFFAOYSA-L 2-(4-carboxylatopyridin-2-yl)pyridine-4-carboxylate;ruthenium(2+) Chemical compound [Ru+2].[O-]C(=O)C1=CC=NC(C=2N=CC=C(C=2)C([O-])=O)=C1 ZZTDEFHCSZAWMD-UHFFFAOYSA-L 0.000 description 1
- QWAFPTWWKUWNDC-UHFFFAOYSA-N 2-(4-carboxypyridin-2-yl)pyridine-4-carboxylic acid;ruthenium Chemical compound [Ru].OC(=O)C1=CC=NC(C=2N=CC=C(C=2)C(O)=O)=C1 QWAFPTWWKUWNDC-UHFFFAOYSA-N 0.000 description 1
- SFPQDYSOPQHZAQ-UHFFFAOYSA-N 2-methoxypropanenitrile Chemical compound COC(C)C#N SFPQDYSOPQHZAQ-UHFFFAOYSA-N 0.000 description 1
- YSHMQTRICHYLGF-UHFFFAOYSA-N 4-tert-butylpyridine Chemical compound CC(C)(C)C1=CC=NC=C1 YSHMQTRICHYLGF-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920004890 Triton X-100 Polymers 0.000 description 1
- 239000013504 Triton X-100 Substances 0.000 description 1
- NLGYJRUXQVPZSU-UHFFFAOYSA-N [Ru].CC1(CC(=NC=C1)C1=NC=CC=C1)C Chemical compound [Ru].CC1(CC(=NC=C1)C1=NC=CC=C1)C NLGYJRUXQVPZSU-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 125000005466 alkylenyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000012080 ambient air Substances 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- LBVWYGNGGJURHQ-UHFFFAOYSA-N dicarbon Chemical compound [C-]#[C+] LBVWYGNGGJURHQ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- 238000009713 electroplating Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000000260 fractional sublimation Methods 0.000 description 1
- 108700039708 galantide Proteins 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000033444 hydroxylation Effects 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000006911 nucleation Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011164 primary particle Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- SXTKLPAVDUGRNA-UHFFFAOYSA-N ruthenium(2+);tetrabutylazanium Chemical compound [Ru+2].CCCC[N+](CCCC)(CCCC)CCCC SXTKLPAVDUGRNA-UHFFFAOYSA-N 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical group OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- AWDRATDZQPNJFN-VAYUFCLWSA-N taurodeoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCCS(O)(=O)=O)C)[C@@]2(C)[C@@H](O)C1 AWDRATDZQPNJFN-VAYUFCLWSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 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
-
- 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
-
- 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/002—Osmium compounds
- C07F15/0026—Osmium compounds without a metal-carbon linkage
-
- 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
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Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.式(Ia)または(lb) MX3Lt(Ia); MXYLt(lb) [式中、Mはルテニウム、オスミウム、鉄、レニウム、およびテクネチウムから 選ばれた遷移金属であり; 個々のXは、独立に、NCS-、Cl-、Br-、I-、CN-、NCO-、H2O 、NCN2 -、非置換またはビニル、第1級、第2級または第3級のアミン、OH およびC1 〜30アルキルから選ばれた少くとも1つの基により置換されたピリジ ン、から選ばれた共リガンドであり; Yは、非置換または少くとも1つのC1 〜30アルキルにより置換された2,2 ’−ビピリジン、o−フェナントロリンから選ばれた共リガンドであり;および 、 Ltは、一般式(IIa)および(IIb) {式中、R1は、H、COOH、PO(OH)2、PO(OR3)(OH)、PO (OR3)2、CO(NHOH);COOH、PO(OH)2、PO(OR3)(O H)、PO(OR3)2およびCO(NHOH)から選ばれた基の少くとも1つに より置換されたフェニル、ピロカテコール基であり;R3は、C1 〜30アルキルお よび フェニルから選ばれ; R2は、H、C1 〜30アルキルおよびフェニルから選ばれ;および、 AおよびBは独立に、式(III a)、(III b)、(III c)、(III d)、 (III e)、および(III f)基から選ばれた同じまたは異なる基: (式中、R4は、R1と同じ意味を有し; 個々のR5、R6、R7、R8、R9、R10およびR11は、R2と同じ意味を有し、 且つ、置換基R1およびR4のうちの少なくとも1つがHと異なる条件下で、R2 、R5、R6、R7、R8、R9、R10およびR11は互いに同じまたは異なる)} から選ばれた式を有する三座配置子である] の光増感剤複合体。 2.Mがルテニウムまたはオスミウムであり; 個々のXは、独立にNCS-およびCN-から選ばれ; Ltは、式(IIa):{式中、R1は、H、COOH、PO(OH)2、PO(OR3)(OH)、PO (OR3)2、CO(NHOH);COOH、PO(OH)2、PO(OR3)(O H)、PO(OR3)2、およびCO(NHOH)から選ばれた基の少なくとも1 つにより置換されたフェニル、ピロカテコール基から選ばれ;R3はC1 〜30アル キルおよびフェニルから選ばれ; AおよびBは、同じまたは異なって、式(III a) (式中、R4は、置換基R1およびR4のうちの少なくとも1つがHと異なる条件 下で、R1と同じ意味を有する)} を有することを特徴とする請求項1に従う式(Ia)の光増感剤複合体。 3.Mはルテニウムまたはオスミウムであり; 個々のXは、独立にNCS-およびCN-から選ばれ;および、 Ltは式(IIa):(式中、R1はCOOH、PO(OH)2、PO(OR3)(OH)およびPO( OR3)2から選ばれた基の少くとも1つにより置換されたフェニルであり;R3 はC1 〜30アルキルおよびフェニルから選ばれ;および、 AおよびBは、両方とも2−ピリジルである) を有することを特徴とする請求項2に従う式(Ia)の光増感剤複合体。 4.Mがルテニウムまたはオスミウムであり; 個々のXは、独立にNOS-およびCN-から選ばれ;および、 Ltが式(IIa): (式中、R1はCOOHであり;および、 AおよびBが両方とも4−カルボキシ−2−ピリジルである) を有することを特徴とする請求項2に従う式(Ia)の光増感剤複合体。 5.Mはルテニウムまたはオスミウムであり; Xは、NCS-またはCN-であり; Yは、非置換または少なくとも1個のC1 〜30アルキルにより置換された2, 2’−ビピリジン、o−フェナントロリンから選ばれ;および、 Ltは式(IIa) {式中、R1は、H;COOH、PO(OH)2、PO(OR3)(OH)、PO (OR3)2およびCO(NHOH)から選ばれた基の少くとも1つにより置換さ れたフェニル、ピロカテコール基か ら選ばれ; R3はC1 〜30アルキルおよびフェニルから選ばれ; AおよびBは、同じまたは異なって、式(III a) (式中、R4は、置換基R1およびR4の少くとも一つがHと異なるという条件下 で、H、COOH、PO(OH)2、PO(OR3)(OH)、PO(OR3)2、 CO(NHOH);COOH、PO(OH)2、PO(OR3)(OH)、PO( OR3)2、およびCO(NHOH)から選ばれた基の少くとも1つにより置換さ れたフェニル、ピロカテコール基から選ばれ;R3は、C1 〜30アルキルおよびフ ェニルから選ばれる) を有する} ことを特徴とする請求項2に従う式(lb)の光増感剤複合体。 6.Mは、ルテニウムまたはオスミウムであり; Xは、NCS-またはCN-であり; Yは、4,4’−ジメチル−2,2’−ピリジンであり;および、 Ltは式(IIa) (式中、R1はCOOH、PO(OH)2、PO(OR3)(OH)、およびPO (OR3)2から選ばれた基の少なくとも1つにより置換されたフェニルであり; R3はC1 〜30アルキルおよびフェニルから選ばれ;および、 AおよびBは、両方とも2−ピリジルである) を有することを特徴とする請求項5に従う式(lb)の光増感剤複合体。 7.少くとも1つの二酸化チタン層が適用された支持体上に堆積された電気的 に伝導性の層を含む光起電力セルであって; それが前記二酸化チタン層に適用された光増感剤として、請求項1で特定され た式(Ia)または(lb)の光増感剤複合体を含むことを特徴とする光起電力 セル。
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PCT/IB1998/000680 WO1998050393A1 (en) | 1997-05-07 | 1998-05-07 | Metal complex photosensitizer and photovoltaic cell |
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- 1998-05-07 JP JP54787198A patent/JP4298799B2/ja not_active Expired - Fee Related
- 1998-05-07 AU AU70704/98A patent/AU743120B2/en not_active Expired
- 1998-05-07 WO PCT/IB1998/000680 patent/WO1998050393A1/en active IP Right Grant
- 1998-05-07 US US09/423,162 patent/US6245988B1/en not_active Expired - Lifetime
- 1998-05-07 ES ES98917480T patent/ES2212286T3/es not_active Expired - Lifetime
- 1998-05-07 DE DE69819712T patent/DE69819712T2/de not_active Expired - Lifetime
- 1998-05-07 EP EP98917480A patent/EP0983282B1/en not_active Expired - Lifetime
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Also Published As
Publication number | Publication date |
---|---|
EP0983282B1 (en) | 2003-11-12 |
JP4298799B2 (ja) | 2009-07-22 |
DE69819712T2 (de) | 2004-09-23 |
AU743120B2 (en) | 2002-01-17 |
EP0983282A1 (en) | 2000-03-08 |
WO1998050393A1 (en) | 1998-11-12 |
DE69819712D1 (de) | 2003-12-18 |
AU7070498A (en) | 1998-11-27 |
ES2212286T3 (es) | 2004-07-16 |
US6245988B1 (en) | 2001-06-12 |
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