EP2880018A1 - Borhaltige perylenmonoimide, verfahren zu deren herstellung, deren verwendung als bausteine zur herstellung von perylenmonoimidderivaten, monoimidderivate und deren verwendung bei farbstoffsensibilisierten solarzellen - Google Patents
Borhaltige perylenmonoimide, verfahren zu deren herstellung, deren verwendung als bausteine zur herstellung von perylenmonoimidderivaten, monoimidderivate und deren verwendung bei farbstoffsensibilisierten solarzellenInfo
- Publication number
- EP2880018A1 EP2880018A1 EP13828249.6A EP13828249A EP2880018A1 EP 2880018 A1 EP2880018 A1 EP 2880018A1 EP 13828249 A EP13828249 A EP 13828249A EP 2880018 A1 EP2880018 A1 EP 2880018A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- general formula
- compounds
- alkyl
- hydrogen
- variables
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 40
- 230000008569 process Effects 0.000 title claims abstract description 39
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 title claims description 37
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 title description 8
- 238000004519 manufacturing process Methods 0.000 title description 5
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title description 3
- 229910052796 boron Inorganic materials 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 121
- 238000002360 preparation method Methods 0.000 claims abstract description 31
- -1 radicals hydrogen Chemical class 0.000 claims description 573
- 229910052739 hydrogen Inorganic materials 0.000 claims description 99
- 239000001257 hydrogen Substances 0.000 claims description 93
- 125000000217 alkyl group Chemical group 0.000 claims description 89
- 125000003118 aryl group Chemical group 0.000 claims description 81
- 125000001072 heteroaryl group Chemical group 0.000 claims description 57
- 150000002431 hydrogen Chemical class 0.000 claims description 39
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 35
- 229910052760 oxygen Inorganic materials 0.000 claims description 35
- 239000001301 oxygen Substances 0.000 claims description 35
- 125000003545 alkoxy group Chemical group 0.000 claims description 34
- 125000004104 aryloxy group Chemical group 0.000 claims description 23
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 22
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 229910052783 alkali metal Inorganic materials 0.000 claims description 21
- 125000004986 diarylamino group Chemical group 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 19
- 229910052727 yttrium Inorganic materials 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 239000000460 chlorine Substances 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 16
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 125000005110 aryl thio group Chemical group 0.000 claims description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- 239000012442 inert solvent Substances 0.000 claims description 12
- 239000011593 sulfur Substances 0.000 claims description 12
- PXACTUVBBMDKRW-UHFFFAOYSA-M 4-bromobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(Br)C=C1 PXACTUVBBMDKRW-UHFFFAOYSA-M 0.000 claims description 9
- SPXOTSHWBDUUMT-UHFFFAOYSA-M 4-nitrobenzenesulfonate Chemical compound [O-][N+](=O)C1=CC=C(S([O-])(=O)=O)C=C1 SPXOTSHWBDUUMT-UHFFFAOYSA-M 0.000 claims description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 9
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 9
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 8
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 8
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 8
- 239000002798 polar solvent Substances 0.000 claims description 7
- MNKCGUKVRJZKEQ-MIXQCLKLSA-N (1z,5z)-cycloocta-1,5-diene;iridium;methanol Chemical compound [Ir].[Ir].OC.OC.C\1C\C=C/CC\C=C/1.C\1C\C=C/CC\C=C/1 MNKCGUKVRJZKEQ-MIXQCLKLSA-N 0.000 claims description 6
- TXNLQUKVUJITMX-UHFFFAOYSA-N 4-tert-butyl-2-(4-tert-butylpyridin-2-yl)pyridine Chemical group CC(C)(C)C1=CC=NC(C=2N=CC=C(C=2)C(C)(C)C)=C1 TXNLQUKVUJITMX-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 239000004912 1,5-cyclooctadiene Substances 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 claims description 3
- 238000006069 Suzuki reaction reaction Methods 0.000 claims description 2
- SYGWYBOJXOGMRU-UHFFFAOYSA-N chembl233051 Chemical compound C1=CC=C2C3=CC(C(N(CCN(C)C)C4=O)=O)=C5C4=CC=CC5=C3SC2=C1 SYGWYBOJXOGMRU-UHFFFAOYSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 58
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- 239000007787 solid Substances 0.000 description 24
- 150000003254 radicals Chemical class 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 20
- 238000005481 NMR spectroscopy Methods 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 229910052786 argon Inorganic materials 0.000 description 10
- 238000004440 column chromatography Methods 0.000 description 10
- 239000010949 copper Substances 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 229910052731 fluorine Inorganic materials 0.000 description 9
- 239000011737 fluorine Substances 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 125000006617 triphenylamine group Chemical group 0.000 description 7
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 238000001819 mass spectrum Methods 0.000 description 6
- 239000004065 semiconductor Substances 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 125000003107 substituted aryl group Chemical group 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 4
- 125000003282 alkyl amino group Chemical group 0.000 description 4
- 125000002877 alkyl aryl group Chemical group 0.000 description 4
- 239000012300 argon atmosphere Substances 0.000 description 4
- 239000011324 bead Substances 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(II) bromide Substances [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- IBWAVZDUXUXUAJ-UHFFFAOYSA-N 12-[4-(2,4,4-trimethylpentan-2-yl)-N-[4-(2,4,4-trimethylpentan-2-yl)phenyl]anilino]-16-azahexacyclo[12.6.2.12,6.011,21.018,22.010,23]tricosa-1(21),2,4,6(23),7,9,11,13,18(22),19-decaene-15,17-dione Chemical compound C1=CC(C(C)(C)CC(C)(C)C)=CC=C1N(C=1C=2C=3C=CC=C4C=CC=C(C=34)C3=CC=C4C(C=23)=C(C(NC4=O)=O)C=1)C1=CC=C(C(C)(C)CC(C)(C)C)C=C1 IBWAVZDUXUXUAJ-UHFFFAOYSA-N 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- GSWCRDNWOZAAIK-UHFFFAOYSA-N 4-(pentan-3-ylcarbamoyl)-8,11-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)perylene-3-carboxylic acid Chemical compound C=1C(=C23)C(C4=5)=CC=C(C(O)=O)C=5C(C(O)=NC(CC)CC)=CC=C4C2=CC(B2OC(C)(C)C(C)(C)O2)=CC3=CC=1B1OC(C)(C)C(C)(C)O1 GSWCRDNWOZAAIK-UHFFFAOYSA-N 0.000 description 3
- MJVPREHTEYJKBS-UHFFFAOYSA-N C1=CC=C2C(C)(C)C3=CC(N(C=4C=C5C(C)(C)C6=CC=CC=C6C5=CC=4)C=4C=C5C6=CC=C7C(=O)N(C(C8=CC=C(C6=C78)C=6C=C(C=C(C5=6)C=4)N(C=4C=C5C(C)(C)C6=CC=CC=C6C5=CC=4)C=4C=C5C(C)(C)C6=CC=CC=C6C5=CC=4)=O)C(CC)CC)=CC=C3C2=C1 Chemical compound C1=CC=C2C(C)(C)C3=CC(N(C=4C=C5C(C)(C)C6=CC=CC=C6C5=CC=4)C=4C=C5C6=CC=C7C(=O)N(C(C8=CC=C(C6=C78)C=6C=C(C=C(C5=6)C=4)N(C=4C=C5C(C)(C)C6=CC=CC=C6C5=CC=4)C=4C=C5C(C)(C)C6=CC=CC=C6C5=CC=4)=O)C(CC)CC)=CC=C3C2=C1 MJVPREHTEYJKBS-UHFFFAOYSA-N 0.000 description 3
- 239000004471 Glycine Substances 0.000 description 3
- 229920006934 PMI Polymers 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 238000005286 illumination Methods 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 3
- 239000004408 titanium dioxide Substances 0.000 description 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- XDXWNHPWWKGTKO-UHFFFAOYSA-N 207739-72-8 Chemical compound C1=CC(OC)=CC=C1N(C=1C=C2C3(C4=CC(=CC=C4C2=CC=1)N(C=1C=CC(OC)=CC=1)C=1C=CC(OC)=CC=1)C1=CC(=CC=C1C1=CC=C(C=C13)N(C=1C=CC(OC)=CC=1)C=1C=CC(OC)=CC=1)N(C=1C=CC(OC)=CC=1)C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 XDXWNHPWWKGTKO-UHFFFAOYSA-N 0.000 description 2
- UUAQSJWPLSCILF-UHFFFAOYSA-N 4-carbamoyl-6-(2-nitrophenyl)perylene-3-carboxylic acid Chemical compound [N+](=O)([O-])C1=C(C=CC=C1)C1=CC(=C2C(=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)C(=O)O)C(O)=N UUAQSJWPLSCILF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- AQNVYZBKNTUQKS-UHFFFAOYSA-N C1=CC(C2=CC(N(C=3C=C4C(C)(C)C5=CC=CC=C5C4=CC=3)C3=CC=C4C5=CC=CC=C5C(C4=C3)(C)C)=CC=3C2=C2C=CC=3)=C3C2=CC=C2C(=O)N(CC(O)=O)C(=O)C1=C32 Chemical compound C1=CC(C2=CC(N(C=3C=C4C(C)(C)C5=CC=CC=C5C4=CC=3)C3=CC=C4C5=CC=CC=C5C(C4=C3)(C)C)=CC=3C2=C2C=CC=3)=C3C2=CC=C2C(=O)N(CC(O)=O)C(=O)C1=C32 AQNVYZBKNTUQKS-UHFFFAOYSA-N 0.000 description 2
- UPCYLWWAHBNECF-UHFFFAOYSA-N C1=CC=C2C(C)(C)C3=CC(N(C=4C=C5C(C)(C)C6=CC=CC=C6C5=CC=4)C=4C=C5C=CC=C6C7=CC=C8C(=O)N(C(C9=CC=C(C7=C89)C(C=4)=C65)=O)C(CC)CC)=CC=C3C2=C1 Chemical compound C1=CC=C2C(C)(C)C3=CC(N(C=4C=C5C(C)(C)C6=CC=CC=C6C5=CC=4)C=4C=C5C=CC=C6C7=CC=C8C(=O)N(C(C9=CC=C(C7=C89)C(C=4)=C65)=O)C(CC)CC)=CC=C3C2=C1 UPCYLWWAHBNECF-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229910021590 Copper(II) bromide Inorganic materials 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 125000002837 carbocyclic group Chemical group 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
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- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- LEKPFOXEZRZPGW-UHFFFAOYSA-N copper;dicyanide Chemical compound [Cu+2].N#[C-].N#[C-] LEKPFOXEZRZPGW-UHFFFAOYSA-N 0.000 description 1
- IDLFZVILOHSSID-OVLDLUHVSA-N corticotropin Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)NC(=O)[C@@H](N)CO)C1=CC=C(O)C=C1 IDLFZVILOHSSID-OVLDLUHVSA-N 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 description 1
- YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000004611 dihydroisoindolyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 1
- 125000005045 dihydroisoquinolinyl group Chemical group C1(NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000006342 heptafluoro i-propyl group Chemical group FC(F)(F)C(F)(*)C(F)(F)F 0.000 description 1
- 125000005553 heteroaryloxy group Chemical group 0.000 description 1
- 125000005368 heteroarylthio group Chemical group 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 description 1
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000011244 liquid electrolyte Substances 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- JIQNWFBLYKVZFY-UHFFFAOYSA-N methoxycyclohexatriene Chemical compound COC1=C[C]=CC=C1 JIQNWFBLYKVZFY-UHFFFAOYSA-N 0.000 description 1
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- LCSMGMWMTSWXDD-UHFFFAOYSA-N n-(9,9-dimethylfluoren-2-yl)-9,9-dimethylfluoren-2-amine Chemical compound C1=CC=C2C(C)(C)C3=CC(NC4=CC=C5C6=CC=CC=C6C(C5=C4)(C)C)=CC=C3C2=C1 LCSMGMWMTSWXDD-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- HAGWGWQUZPWZER-UHFFFAOYSA-N n-prop-1-enylbutan-2-imine Chemical group CCC(C)=NC=CC HAGWGWQUZPWZER-UHFFFAOYSA-N 0.000 description 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 1
- 125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- PQPFFKCJENSZKL-UHFFFAOYSA-N pentan-3-amine Chemical compound CCC(N)CC PQPFFKCJENSZKL-UHFFFAOYSA-N 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 231100000289 photo-effect Toxicity 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 1
- 229920000301 poly(3-hexylthiophene-2,5-diyl) polymer Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 125000004424 polypyridyl Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 description 1
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 description 1
- 125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- CMJDSHGPZPMYQN-UHFFFAOYSA-N sodium;2-(4-butoxyphenyl)-n-oxidoacetamide Chemical compound [Na+].CCCCOC1=CC=C(CC(=O)N[O-])C=C1 CMJDSHGPZPMYQN-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005118 spray pyrolysis Methods 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/18—Ring systems of four or more rings
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/04—Esters of boric acids
-
- 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/62—Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/70—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with ring systems containing two or more relevant rings
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
-
- 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
- C09B13/00—Oxyketone dyes
- C09B13/04—Oxyketone dyes of the pyrene series
-
- 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
- C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
- C09B3/50—Dibenzopyrenequinones
-
- 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
- H01G9/2063—Light-sensitive devices comprising an organic dye as the active light absorbing material, e.g. adsorbed on an electrode or dissolved in solution comprising a mixture of two or more dyes
-
- 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
- Y02B—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO BUILDINGS, e.g. HOUSING, HOUSE APPLIANCES OR RELATED END-USER APPLICATIONS
- Y02B10/00—Integration of renewable energy sources in buildings
- Y02B10/10—Photovoltaic [PV]
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P80/00—Climate change mitigation technologies for sector-wide applications
- Y02P80/20—Climate change mitigation technologies for sector-wide applications using renewable energy
Definitions
- the present invention relates to compounds of general formula I
- E 2 is bound either to the 8 or 9 position of the perylene skeleton and is identical to E 1 ,
- W a bridging C2 or C3 moiety which may be substituted by one or more alkyl
- R 3 identical or different radicals hydrogen, alkyl, cycloalkyl, aryl, hetaryl, alkoxy,
- Y oxygen or NR 12 and hydrogen, alkyl, cycloalkyl, aryl or hetaryl,
- A is -COOM, -SO3M or -PO3M
- M hydrogen, alkali metal cation or [NR ' ] 4+ , hydrogen or alkyl, where the radicals R ' may be identical or different, and
- Lg leaving group m 0 or 1 , where in the case of m equal 1 the one Lg is bound either to the 8 or 9
- R 1 , R 2 independently of each other a moiety of formula Ilia
- the direct conversion of solar energy to electrical energy in solar cells is based on the internal photoeffect of a semiconductor material, i.e. the generation of electron-hole pairs by absorption of photons and the separation of the negative and positive charge carriers at a p-n junction or a Schottky contact.
- the photovoltage thus generated can bring about a photocurrent in an external circuit, through which the solar cell delivers its power.
- Thin layers or films of metal oxides are known to constitute inexpensive solid semiconductor materials (n-semiconductors), but their absorption, owing to large band gaps, is typically not within the visible region of the electromagnetic spectrum.
- the metal oxides therefore have to be combined with a photosensitizer which absorbs in the wavelength range of sunlight, i.e. at from 300 to 2000 nm, and, in the electronically excited state, injects electrons into the conduction band of the semiconductor. With the aid of a redox system which is used additionally in the cell and is reduced at the counterelectrode, electrons are recycled to the sensitizer which is thus regenerated.
- DSCs Dye-sensitized solar cells which are based on titanium dioxide as the semiconductor material are described, for example, in US-A-4 927 721 , Nature 353, p. 737-740 (1991 ) and US- A-5 350 644, and also Nature 395, p. 583-585 (1998) and EP-A-1 176 646.
- These solar cells comprise monomolecular films of transition metal complexes, especially ruthenium complexes, which are bonded to the titanium dioxide layer via acid groups, as sensitizers and iodine/iodide redox systems present in dissolved form or amorphous organic p-conductors based on spirobifluorenes.
- metal-free organic dyes have attracted increasing attention as they do not contain any toxic or costly metal and their properties are easily tuned by facile structural modification.
- they generally have much higher extinction coefficients when compared to Ru(ll) polypyridyls, making them excellent for use in solid state DSCs in combination with hole transporting materials such as P3HT as shown, for example, by G. K. Mor, S. Kim, M. Paulose, O. K. Varghese, K. Shankar, J. Basham and C. A. Grimes, Nano Lett., 2009, 9, 4250, or spiro-MeOTAD as shown, for example, by H. J. Snaith, A. J. Moule, C. Klein, K. Meerholz, R. H. Friend, M. Gratzel, Nano Lett., 2007, 7, 3372.
- T. Teraoka, S. Hiroto and H. Shinokubo (Org. Lett. 201 1 , Vol. 13, No. 10, 2532-2535) and G. Battagliarin, C. Li, V. Enkelmann and K. Mullen (Org. Lett. 201 1 , Vol. 13, No. 12, 3012-3015) describe the preparation of the 2,5,8,1 1-tetraboronic ester erylenediimides
- E 2 is bound either to the 8 or 9 position of the perylene skeleton and is identical to E 1 ,
- W a bridging C2 or C3 moiety which may be substituted by one or more alkyl
- R 3 identical or different radicals hydrogen, alkyl, cycloalkyi, aryl, hetaryl, alkoxy,
- R 12 hydrogen, alkyl, cycloalkyi, aryl or hetaryl, or a moiety of formula -Z-A, wherein is -COOM, -SO3M or -PO3M, M hydrogen, alkali metal cation or [NR ' ] 4+ ,
- R ' hydrogen or alkyl, where the radicals R ' may be identical or different, and
- Ci-C6-alkylene or 1 ,4-phenylene where the phenylene radical may be substituted by one or more substituents alkyl, nitro, cyano and/or halogen.
- Preferred compounds of general formula I are those wherein the variables have the following meaning
- E , E 2 a moiety selected from the group consisting of
- E , E 2 a moiety selected from the group consisting of
- E 2 is bound either to the 8 or 9 position of the perylene skeleton and is identical to E 1 ,
- R 3 identical or different radicals hydrogen, alkyl, cycloalkyl, aryl, alkoxy, aryloxy,
- R 12 alkyl, or a moiety of formula -Z-A, wherein
- A is -COOM
- R ' hydrogen or alkyl, where the radicals R ' may be identical or different and
- Z is Ci-C6-alkylene or 1 ,4-phenylene.
- a further objective of the instant invention is a process for the preparation of compounds of general formula I which comprises reacting a compound of general formula I*
- R 3 identical or different radicals hydrogen, alkyl, cycloalkyi, aryl, hetaryl, alkoxy, aryloxy, arylthio, hetaryloxy, hetarylthio, diarylamino or dialkylamino, n 0, 1 , 2, 3 or 4
- R12 hydrogen, alkyl, cycloalkyi, aryl or hetaryl, or a moiety of formula -Z-A, wherein
- A is -COOM, -SO3M or -PO3M
- R ' hydrogen or alkyl, where the radicals R ' may be identical or different, and
- Ci-C6-alkylene or 1 ,4-phenylene where the phenylene radical may be substituted by one or more substituents alkyl, nitro, cyano and/or halogen.
- a preferred process for the preparation of compounds of general formula I according to the instant invention comprises reacting a compound of general for
- R 3 identical or different radicals hydrogen, alkyl, cycloalkyl, aryl, hetaryl, alkoxy,
- R 12 hydrogen, alkyl, cycloalkyl, aryl or hetaryl, or a moiety of formula -Z-A, wherein
- A is -COOM, -SOsM or -P0 3 M
- R ' hydrogen or alkyl, where the radicals R ' may be identical or different, and
- a specifically preferred process for the preparation of compounds of general formula I according to the instant invention comprises reacting a compound of general for
- R 3 identical or different radicals hydrogen, alkyl, cycloalkyl, aryl, alkoxy, aryloxy,
- R 12 alkyl, or a moiety of formula -Z-A, wherein
- A is -COOM
- R ' hydrogen or alkyl, where the radicals R ' may be identical or different and
- Z is Ci-C6-alkylene or 1 ,4-phenylene.
- ambient pressure denotes basically unconfined reaction conditions, however, not excluding the application of protective gas atmosphere in order to avoid adverse effects by oxygen/air and/or moisture.
- Inert solvent means a solvent which does not contain moieties with either basic or acidic properties. Especially groups with acidic hydrogen atoms must not be present. In the case of a aromatic or heteroaromatic solvent this may only contain less than three neighboring hydrogen atoms directly bound to the carbon atoms or heteroatoms of the aromatic or heteroaromatic solvent skeleton in order to prevent the aromatic or heteroaromtic solvent from reacting with the boron containing educt.
- inert solvent is meant to embrace mixtures of inert solvents as well.
- Suitable inert solvents are e.g. dimethyl formamide (DMF), tetrahydofuran (THF), 1 ,4-dioxan, octane, hexane, pentane, mesitylene, pinacolone etc. and mixtures thereof.
- a further objective of the instant invention is to provide a process for the preparation of compounds of general formula I I
- Lg leaving group m 0 or 1 , where in the case of m equal 1 the one Lg is bound either to the 8 or 9 position of the perylene skeleton and is identical to the Lg bound to the 1 1 position, and the remaining variables R 3 , n and Y have the meaning according to general formula I shown above and preferred embodiments thereof, which comprises reacting a compound of general formula I or preferred embodiments thereof as described above or reacting a compound prepared according to the aforementioned process or preferred embodiments of said process with a compound Cu(Lg)2 in the presence of a polar solvent under confined conditions and temperatures between 20°C and 140°C.
- Lg chlorine, bromine, iodine, brosylate, nosylate, tosylate, mesylate or triflate, m 0 or 1 , where in the case of m equal 1 the one Lg is bound either to the 8 or 9
- confined conditions refers to reaction conditions in which the reactants during the reaction are placed in a tightly sealed reaction vessel, ampoule or the like.
- Polar solvent typically refers to a solvent which is readilly miscible with water.
- polar solvent is meant to embrace mixtures of polar solvents as well. Suitable polar solvents are e.g. water, dimethyl formamide (DMF), tetrahydofuran (THF), 1 ,4-dioxan, short carbon chain alcohols like e.g. butanol, i-butanol, tert.-butanol, propanol, i-propanol, ethanol or methanol and mixtures thereof.
- DMF dimethyl formamide
- THF tetrahydofuran
- 1 ,4-dioxan short carbon chain alcohols like e.g. butanol, i-butanol, tert.-butanol, propanol, i-propanol, ethanol or methanol and mixtures thereof.
- the leaving group Lg can be any group known to a person skilled in the art as being prone to easily leave the molecule.
- Lg consists of or comprises strongly electron- withdrawing atoms or moieties and, thus, is normally split off as anionic species.
- Preferred groups Lg are chlorine, bromine, iodine, brosylate, nosylate, tosylate, mesylate and triflate which, in view of the aforesaid, leave the molecule as chloride, bromide, iodide, brosylate, nosylate, tosylate, mesylate ("mes" - H3C-SO3 " ) or triflate ("tri” - F3C-SO3 " ) anion.
- brosylate brosylate
- nosylate nosylate
- tosylate tosylate
- preferred reagents Cu(Lg)2 are CuC , CuBr2, Cub, Cu(bros)2, Cu(nos)2, Cu(tos)2,
- R 3 identical or different radicals hydrogen, alkyl, cycloalkyi, aryl, hetaryl, alkoxy, aryloxy, arylthio, hetaryloxy, hetarylthio, diarylamino or dialkylamino,
- R12 hydrogen, alkyl, cycloalkyi, aryl or hetaryl, or a moiety of formula -Z-A, wherein is -COOM, -SOsM or -P0 3 M,
- M hydrogen, alkali metal cation or [NR ' ] 4+ , hydrogen or alkyl, where the radicals R ' may be identical or different, and
- Ci-C6-alkylene or 1 ,4-phenylene where the phenylene radical may be substituted by one or more substituents alkyl, nitro, cyano and/or halogen.
- Lg chlorine, bromine, iodine, brosylate, nosylate, tosylate, mesylate or triflate, m 0 or 1 , where in the case of m equal 1 the one Lg is bound either to the 8 or 9 position of the perylene skeleton and is identical to the Lg bound to the 1 1 position,
- R 3 identical or different radicals hydrogen, alkyl, cycloalkyi, aryl, alkoxy, aryloxy,
- R 12 alkyl, or a moiety of formula -Z-A, wherein
- A is -COOM
- R ' hydrogen or alkyl, where the radicals R ' may be identical or different, and
- Ci-C6-alkylene or 1 ,4-phenylene.
- a further objective of the instant invention is a process for the preparation of compounds of general formula III
- R 1 , R 2 independently of each other a moiety of formula Ilia
- R 5 independently of each other aryl or hetaryl, m 0 or 1 , where in the case of m equal 1 R 2 is bound either to the 8 or 9 position of the perylene skeleton, and the remaining variables R 3 , n and Y have the aforementioned meaning according to general formula II and its preferred embodiment comprising reacting a compound of general formula II or its preferred embodiment with a compound or a mixture of compounds of general formula Ilia *
- R 4 , R 5 independently of each other moieties of formulae lb or lc
- R 6 hydrogen, alkyl, aryl, alkoxy, alkylthio or -NR 7 R 8 , where in case of two or more
- R 7 to R 11 hydrogen, alkyl, cycloalkyl, aryl or hetaryl, and the remaining variables R 3 , n and Y have the aforementioned meaning according to general formula II and its preferred embodiment.
- the Buchwald-Hartwig amination reaction is a well established synthetic route and the reaction conditions can easily be determined by a person skilled in the art. Conversion of aryl bromides to arylamines is specifically addressed in the publication by Guram, A.S.; Rennels, R.A.;
- R 3 identical or different radicals hydrogen, alkyl, cycloalkyi, aryl, hetaryl, alkoxy,
- R12 hydrogen, alkyl, cycloalkyi, aryl or hetaryl, or a moiety of formula -Z-A, wherein
- A is -COOM, -SOsM or -P0 3 M
- R ' hydrogen or alkyl, where the radicals R ' may be identical or different, and
- Ci-C6-alkylene or 1 ,4-phenylene where the phenylene radical may be substituted by one or more substituents alkyl, nitro, cyano and/or halogen.
- R 4 , R 5 independently of each other aryl or hetaryl, m 0 or 1 , where in the case of m equal 1 the respective R 2 is bound either to the 8 or 9 position of the perylene skeleton,
- R 3 identical or different radicals hydrogen, alkyl, cycloalkyi, aryl, alkoxy, aryloxy,
- R 2 alkyl, or a moiety of formula -Z-A, wherein
- A is -COOM
- R ' hydrogen or alkyl, where the radicals R ' may be identical or different, and
- Ci-C6-alkylene or 1 ,4-phenylene.
- R 4 m 0 or 1 , where in the case of m equal 1 R 2 is bound either to the 8 or 9 position of the perylene skeleton,
- R 4 , R 5 independently of each other moieties of formulae lb or lc
- R 6 hydrogen, alkyl, aryl, alkoxy, alkylthio or -NR 7 R 8 , where in case of two or more substituents (p equal or greater than 2) these may be identical or different,
- R 3 identical or different radicals hydrogen, alkyl, cycloalkyi, aryl, hetaryl, alkoxy,
- R 12 hydrogen, alkyl, cycloalkyl, aryl or hetaryl, or a moiety of formula -Z-A, wherein is -COOM, -SOsM or -P0 3 M,
- R ' hydrogen or alkyl, where the radicals R ' may be identical or different, and
- R 6 hydrogen, alkyl, aryl, alkoxy, alkylthio or -N R 7 R 8 , where in case of two or more substituents (p equal or greater than 2) these may be identical or different, p 0, 1 , 2, 3, 4 or 5,
- R 7 to R 1 1 hydrogen, alkyl, cycloalkyi, aryl or hetaryl,
- R 3 identical or different radicals hydrogen, alkyl, cycloalkyi, aryl, alkoxy, aryloxy, diarylamino or dialkylamino, n 0, 1 , 2, 3 or 4
- R 12 alkyl, or a moiety of formula -Z-A, wherein A is -COOM,
- R ' hydrogen or alkyl, where the radicals R ' may be identical or different, and
- Ci-C6-alkylene or 1 ,4-phenylene.
- a further objective of the instant invention is a process for the preparation of compounds of general formula IV (R 3 In
- R 13 , R 14 independently of each other aryl or hetaryl, leaving group, m 0 or 1 , where in the case of m equal 1 R 14 is bound either to the 8 or 9 position of the perylene skeleton, and the remaining variables R 3 , n and Y have the meaning according to general formula I and its preferred embodiments, which comprises reacting a compound of general formula I or preferred embodiments of such compounds with compounds of general formula Lg-R 13 and Lg-R 14 in the presence of a palladium containing catalyst under the conditions of the Suzuki coupling reaction.
- R 13 , R 14 independently of each other moieties of formulae IVa or IVb
- R15 hydrogen, alkyl, aryl, alkoxy, alkylthio or -NR 16 R 17 , where in case of two or more substituents (q equal or greater than 2) these may be identical or different, q 0, 1 , 2, 3, 4 or 5,
- R 20 hydrogen, alkyl, aryl or hetaryl, m 0 or 1 , where in the case of m equal 1 R 14 is bound either to the 8 or 9 position of the perylene skeleton, and the remaining variables R 3 , n and Y have the meaning according to general formula I and the preferred embodiments thereof.
- a further objective of the instant invention are compounds of general formula IV
- R 13 , R 14 independently of each other aryl or hetaryl, m 0 or 1 , where in the case of m equal 1 R 14 is bound either to the 8 or 9 position of the perylene skeleton and is identical to R 13 ,
- R 3 identical or different radicals hydrogen, alkyl, cycloalkyl, aryl, hetaryl, alkoxy, aryloxy, arylthio, hetaryloxy, hetarylthio, diarylamino or dialkylamino, n 0, 1 , 2, 3 or 4
- Y oxygen or NR 12 and R 12 hydrogen, alkyl, cycloalkyi, aryl or hetaryl, or a moiety of formula -Z-A, wherein
- A is -COOM, -SO3M or -PO3M
- R ' hydrogen or alkyl, where the radicals R ' may be identical or different, and
- Ci-C6-alkylene or 1 ,4-phenylene where the phenylene radical may be substituted by one or more substituents alkyl, nitro, cyano and/or halogen.
- a further objective of the instant invention are compounds of general formula IV
- R 13 , R 14 independently of each other aryl or hetaryl, m 0 or 1 , where in the case of m equal 1 R 14 is bound either to the 8 or 9 position of the perylene skeleton and is identical to R 13 ,
- R 3 identical or different radicals hydrogen, alkyl, cycloalkyi, aryl, hetaryl, alkoxy, aryloxy, arylthio, hetaryloxy, hetarylthio, diarylamino or dialkylamino, n 0, 1 , 2, 3 or 4
- R 12 hydrogen, alkyl, cycloalkyi, aryl or hetaryl, or a moiety of formula -Z-A, wherein
- A is -COOM, -SO3M or -PO3M
- R ' hydrogen or alkyl, where the radicals R ' may be identical or different, and
- Ci-C6-alkylene or 1 ,4-phenylene where the phenylene radical may be substituted by one or more substituents alkyl, nitro, cyano and/or halogen.
- R 13 , R 14 independently of each other aryl or hetaryl, m 0 or 1 , where in the case of m equal 1 R 14 is bound either to the 8 or 9 position of the perylene skeleton and is identical to R 13 ,
- R 3 identical or different radicals hydrogen, alkyl, cycloalkyi, aryl, alkoxy, aryloxy, diarylamino or dialkylamino, n 0, 1 , 2, 3 or 4 Y oxygen or N R 12 , and
- R 12 alkyl, or a moiety of formula -Z-A, wherein is -COOM,
- R ' hydrogen or alkyl, where the radicals R ' may be identical or different,
- Ci-C6-alkylene or 1 ,4-phenylene isoethylene
- R 13 R 14 independently of each other moieties of formulae IVa or IVb
- R 15 hydrogen, alkyl, aryl, alkoxy, alkylthio or -NR 16 R 17 , where in case of two or more substituents (q equal or greater than 2) these may be identical or different, q 0, 1 , 2, 3, 4 or 5, X C(R 18 R 19 ) 2 , N R 20 , oxygen or sulfur,
- R 16 to R 20 hydrogen, alkyl, aryl or hetaryl, m 0 or 1 , where in the case of m equal 1 R 14 is bound either to the 8 or 9 position of the perylene skeleton and is identical to R 13 ,
- R 3 identical or different radicals hydrogen, alkyl, cycloalkyi, aryl, hetaryl, alkoxy, aryloxy, arylthio, hetaryloxy, hetarylthio, diarylamino or dialkylamino, n 0, 1 , 2, 3 or 4
- R 12 hydrogen, alkyl, cycloalkyi, aryl or hetaryl, or a moiety of formula -Z-A, wherein
- A is -COOM, -SOsM or -P0 3 M
- R ' hydrogen or alkyl, where the radicals R ' may be identical or different, and
- Ci-C6-alkylene or 1 ,4-phenylene where the phenylene radical may be substituted by one or more substituents alkyl, nitro, cyano and/or halogen.
- R 15 hydrogen, alkyl, aryl, alkoxy, alkylthio or -NR 16 R 17 , where in case of two or more substituents (q equal or greater than 2) these may be identical or different,
- R 16 to R 20 hydrogen, alkyl, aryl or hetaryl, m 0 or 1 , where in the case of m equal 1 R 14 is bound either to the 8 or 9 position of the perylene skeleton and is identical to R 13 ,
- R 3 identical or different radicals hydrogen, alkyl, cycloalkyi, aryl, alkoxy, aryloxy, diarylamino or dialkylamino,
- R12 alkyl or a moiety of formula -Z-A, wherein
- A is -COOM
- R ' hydrogen or alkyl, where the radicals R ' may be identical or different,
- Ci-C6-alkylene or 1 ,4-phenylene.
- a further objective or the instant invention is the use of compounds of general formula I I prepared according to abovementioned process and its preferred embodiments, of compounds of general formula II I prepared according to the abovementioned process and its preferred embodiments, of compounds of general formula IV prepared according to the abovementioned process and its preferred embodiments, of compounds of general formula I I and their preferred abovementioned embodiments, of compounds of claim 12 and their preferred abovementioned embodiments and of compounds of general formula IV and their preferred abovementioned embodiments for the preparation of dye-sensitized solar cells.
- a further objective or the instant invention is a dye-sensitized solar cell comprising compounds of general formula II I prepared according to the abovementioned process and its preferred embodiments, compounds of general formula IV prepared according to the abovementioned process and its preferred embodiments, compounds of general formula II and their preferred abovementioned embodiments, compounds of claim 12 and their preferred abovementioned embodiments or compounds of general formula IV and their preferred abovementioned embodiments.
- alkyl, aryl or heteroaryl represents unsubstituted or substituted alkyl, unsubstituted or substituted aryl or unsubstituted or substituted heteroaryl.
- Alkyl comprises straight-chain or branched alkyl.
- Alkyl is preferably Ci-C3o-alkyl, especially Ci- C2o-alkyl and most preferably Ci-Ci2-alkyl.
- alkyl groups are especially methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n- octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-hexadecyl, n-octadecyl and n-eicosyl.
- branched alkyl groups can be represented by the following formula
- R a is selected from Ci- to C28-alkyl, where the sum of the carbon atoms of the Rs
- radicals is an integer from 2 to 29.
- R a radicals are preferably selected from Ci- to Ci2-alkyl, especially Ci- to Cs-alkyl.
- Preferred branched alkyl radicals of the above formula are, for example:
- 1-pentadecyloctacosanyl 1-tetradecyloctacosanyl, 1-tridecyloctacosanyl, 1-dodecyloctacosanyl, 1-undecyloctacosanyl, 1-decyloctacosanyl, 1-nonyloctacosanyl, 1-octyloctacosanyl, 1- heptyloctacosanyl, 1-hexyloctacosanyl, 1-pentyloctacosanyl, 1-butyloctacosanyl, 1- propyloctacosanyl, 1-ethyloctacosanyl, 1-methyloctacosanyl.
- AlkyI also comprises alkyl radicals whose carbon chains may be interrupted by one or more nonadjacent groups selected from oxygen, sulfur, -CO-, -NR b -, -SO- and/or -SO2- where R b is preferably hydrogen, unsubstituted straight-chain or branched alkyl as described before or unsubstituted aryl as described below.
- Substituted alkyl groups may, depending on the length of the alkyl chain, have one or more (e.g. 1,2,3,4,5 or more than 5) substituents. These are preferably each independently selected from cycloalkyl, heterocycloalkyl, aryl, hetaryl, fluorine, chlorine, bromine, cyano and nitro.
- Aryl-substituted alkyl radicals have at least one unsubstituted or substituted aryl group, as defined below.
- the alkyl group of the aralkyi radical may bear at least one further substituent and/or be interrupted by one or more nonadjacent groups selected from oxygen, sulfur, -CO-, - NR b -, -SO- and/or -SO2- where R b is preferably hydrogen, unsubstituted straight-chain or branched alkyl as described before or unsubstituted aryl as described below.
- Arylalkyl is preferably phenyl-Ci-Cio-alkyl, more preferably phenyl-Ci-C4-alkyl, for example benzyl, 1 -phenethyl, 2-phenethyl, 1 -phenprop-1-yl, 2-phenprop-1 -yl, 3-phenprop-1 -yl, 1 -phenbut-1 -yl, 2- phenbut-1 -yl, 3-phenbut-1 -yl, 4-phenbut-1 -yl, 1 -phenbut-2-yl, 2-phenbut-2-yl, 3-phenbut-2-yl,
- Halogen-substituted alkyi groups comprise a straight-chain or branched alkyi group in which at least one hydrogen atom or all hydrogen atoms are replaced by halogen.
- the halogen atoms are preferably selected from fluorine, chlorine and bromine, especially fluorine and chlorine.
- haloalkyi groups are especially chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 1 -bromoethyl, 1 -fluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2- difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl,
- unsubstituted and substituted alkyi radicals which may be interrupted by one or more nonadjacent groups selected from oxygen, sulfur, -NR b -, -CO-, -SO- and/or -
- dicyclopentylamino dicyclohexylamino, dicycloheptylamino, diphenylamino and dibenzylamino; formylamino, acetylamino, propionylamino and benzoylamino; carbamoyl, methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, butyl- aminocarbonyl, pentylaminocarbonyl, hexylaminocarbonyl, heptylaminocarbonyl,
- octylaminocarbonyl nonylaminocarbonyl, decylaminocarbonyl and phenylamino-carbonyl; aminosulfonyl, n-dodecylaminosulfonyl, ⁇ , ⁇ -diphenylaminosulfonyl, and
- N,N-bis(4-chlorophenyl)aminosulfonyl methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl hexoxycarbonyl, dodecyloxycarbonyl, octadecyloxycarbonyl, phenoxycarbonyl, (4-tert-butylphenoxy)carbonyl and
- dodecyloxysulfonyl and octadecyloxysulfonyl dodecyloxysulfonyl and octadecyloxysulfonyl.
- cycloalkyi denotes a cycloaliphatic radical having preferably 3 to 10, more preferably 5 to 8, carbon atoms.
- Examples of cycloalkyi groups are especially cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.
- Substituted cycloalkyi groups may, depending on the ring size, have one or more (e.g. 1 , 2, 3, 4, 5 or more than 5) substituents. These are preferably each independently selected from alkyl, alkoxy, alkylamino, alkylthio, cycloalkyi, heterocycloalkyl, aryl, hetaryl, fluorine, chlorine, bromine, cyano and nitro. In the case of substitution, the cycloalkyi groups preferably bear one or more, for example one, two, three, four or five, Ci-C6-alkyl groups.
- substituted cycloalkyi groups are especially 2- and 3-methylcyclopentyl, 2- and 3-ethylcyclopentyl, 2-, 3- and 4-methylcyclohexyl, 2-, 3- and 4-ethylcyclohexyl, 2-, 3- and 4-propylcyclohexyl, 2-, 3- and 4-isopropylcyclohexyl, 2-, 3- and 4-butylcyclohexyl, 2-, 3- and 4-sec.
- substituted and unsubstituted cycloalkyi groups are cyclopropyl, cyclobutyl, cyclopentyl, 2- and 3-methylcyclopentyl, 2- and 3-ethylcyclo-pentyl, cyclohexyl, 2-, 3- and 4-methylcyclohexyl, 2-, 3- and 4-ethylcyclohexyl, 3- and 4-propylcyclohexyl, 3- and 4- isopropylcyclohexyl, 3- and 4-butylcyclohexyl, 3- and 4-sec-butylcyclohexyl, 3- and 4-tert- butylcyclohexyl, cycloheptyl, 2-, 3- and 4-methyl-cycloheptyl, 2-, 3- and 4-ethylcycloheptyl, 3- and 4-propylcycloheptyl, 3- and 4-iso-propylcycloheptyl, 3- and 4-butylcycloheptyl,
- aryl comprises mono- or polycyclic aromatic hydrocarbon radicals and monocyclic aromatic hydrocarbon radicals which may be fused to one or more unfused or fused saturated or unsaturated carbocyclic or heterocyclic five or six membered rings.
- Aryl has preferably 6 to 14, more preferably 6 to 10, carbon atoms. Examples of aryl are especially phenyl, naphthyl, indenyl, fluorenyl, anthracenyl, phenanthrenyl, naphthacenyl, chrysenyl and pyrenyl, especially phenyl, naphthyl and fluorenyl.
- Substituted aryls may, depending on the number and size of their ring systems, have one or more (e.g. 1 , 2, 3, 4, 5 or more than 5) substituents. These are preferably each independently selected from alkyi, alkoxy, alkylamino, alkylthio, cycloalkyl, heterocycloalkyl, aryl, hetaryl, fluorine, chlorine, bromine, cyano and nitro.
- the alkyi, alkoxy, alkylamino, alkylthio, cycloalkyl, heterocycloalkyl, aryl and hetaryl substituents on the aryl may in turn be unsubstituted or substituted.
- the substituents on the aryl are preferably selected from alkyi, alkoxy, haloalkyl, haloalkoxy, aryl, fluorine, chlorine, bromine, cyano and nitro.
- Substituted aryl is more preferably substituted phenyl which generally bears 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, substituents.
- Substituted aryl is preferably aryl substituted by at least one alkyi group ("alkaryl").
- Alkaryl groups may, depending on the size of the aromatic ring system, have one or more (e.g. 1 , 2, 3, 4, 5, 6, 7, 8, 9 or more than 9) alkyi substituents.
- the alkyi substituents may be unsubstituted or substituted. In this regard, reference is made to the above statements regarding unsubstituted and substituted alkyi.
- the alkaryl groups have exclusively unsubstituted alkyi substituents.
- Alkaryl is preferably phenyl which bears 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, more preferably 1 or 2, alkyi substituents.
- Aryl which bears one or more radicals is, for example, 2-, 3- and 4-methylphenyl, 2,4-, 2,5-, 3,5- and 2,6-dimethylphenyl, 2,4,6-trimethylphenyl, 2-, 3- and 4-ethylphenyl, 2,4-, 2,5-, 3,5- and 2,6- diethylphenyl, 2,4,6-triethylphenyl, 2-, 3- and 4-propylphenyl, 2,4-, 2,5-, 3,5- and 2,6- dipropylphenyl, 2,4,6-tripropylphenyl, 2-, 3- and 4-isopropylphenyl, 2,4-, 2,5-, 3,5- and
- hetaryl comprises heteroaromatic, mono- or polycyclic groups and monocyclic groups which may be fused to one or more unfused or fused saturated or unsaturated carbocyclic or heterocyclic five or six membered rings.
- ring carbon atoms these have 1 , 2, 3, 4 or more than 4 of the ring heteroatoms.
- the heteroatoms are preferably selected from oxygen, nitrogen, selenium and sulfur.
- the hetaryl groups have preferably 5 to 18, e.g. 5, 6, 8, 9, 10, 1 1 , 12, 13 or 14, ring atoms.
- Monocyclic hetaryl groups are preferably 5- or 6-membered hetaryl groups, such as 2-furyl (furan-2-yl), 3-furyl (furan-3-yl), 2-thienyl (thiophen-2-yl), 3-thienyl (thiophen-3-yl), selenophen-2- yl, selenophen-3-yl, 1 H-pyrrol-2-yl, 1 H-pyrrol-3-yl, pyrrol-1 -yl, imidazol-2-yl, imidazol-1 -yl, imidazol-4-yl, pyrazol-1 -yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, 3-isoxazolyl, 4-isoxazolyl, 5- isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 2-oxazolyl, 4-oxazoly
- Polycyclic hetaryl has 2, 3, 4 or more than 4 fused rings.
- the fused-on rings may be aromatic, saturated or partly unsaturated.
- Examples of polycyclic hetaryl groups are quinolinyl, isoquinolinyl, indolyl, isoindolyl, indolizinyl, benzofuranyl, isobenzofuranyl, benzothiophenyl, benzoxazolyl, benzisoxazolyl, benzthiazolyl, benzoxadiazolyl; benzothiadiazolyl, benzoxazinyl, benzopyrazolyl, benzimidazolyl, benzotriazolyl, benzotriazinyl, benzoselenophenyl,
- thienothiophenyl thienopyrimidyl, thiazolothiazolyl, dibenzopyrrolyl (carbazolyl), dibenzofuranyl, dibenzothiophenyl, naphtho[2,3-b]thiophenyl, naphtha[2,3-b]furyl, dihydroindolyl,
- dihydroindolizinyl dihydroisoindolyl, dihydroquinolinyl, dihydroisoquinolinyl.
- Substituted heteroaryls may, depending on the number and size of their ring systems, have one or more (e.g. 1 , 2, 3, 4, 5 or more than 5) substituents. These are preferably each independently selected from alkyl, alkoxy, alkylamino, alkylthio, cycloalkyl, heterocycloalkyl, aryl, hetaryl, fluorine, chlorine, bromine, cyano and nitro.
- Halogen substituents are preferably fluorine, chlorine or bromine.
- the substituents are preferably selected from Ci-C6-alkyl, Ci-C6-alkoxy, hydroxyl, carboxyl, halogen and cyano.
- Halogen represents fluorine, chlorine, bromine or iodine, preferably chlorine and bromine.
- Alkali cation represents sodium, potassium, rubidium and cesium, preferably sodium and potassium.
- R ' in the tetraalkyl ammonium cation [NR ' ] 4+ typically refers to methyl or tert.-butyl.
- DSCs generally comprise the following elements: an electrically conductive layer (being part of or forming the working electrode or anode), a photosensitive layer generally comprising a semi- conductive metal oxide and a photosensitive dye, a charge transfer layer and another electrically conductive layer (being part of or forming the counter electrode or cathode).
- N-(1 -ethylpropyl)-2,5-bis[3,3-dimethylbutyl]perylene-3,4-dicarboxylic acid monoimide (0.100 g, 0.179 mmol), bis(pinacolato)diboron (0.100 g, 0.393 mmol), [lr(OMe)cod] 2 (bis(1 ,5- cyclooctadiene)dimethoxydiiridium; 5.9 mg, 8.9 ⁇ ) and dtbpy (4,4'-di-tert-butyl-2,2'-bipyridyl; 4.8 mg, 17.9 ⁇ ) were mixed in an oven dried flask under argon atmosphere.
- UV-vis(in toluene) A max (e [M- crrv 1 ]): 481 nm (2.98 x 10 4 M- crrv 1 ), 509 nm (2.83 x 10 4 M- crrv 1 ).
- the monoborylated compound also according to general formula I of the present invention
- N-(1 -ethylpropyl)-8,1 1 -bis[4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-y]-perylene-3,4-dicarboxylic acid monoimide (0.600 g, 0.933 mmol) was suspended in a mixture of dioxane (100 ml), methanol (10 ml) and water (10 ml) in a 210 mL pressure vial . Copper(ll) bromide (2.08 g, 9.33 mmol) was added, the vessel sealed and heated up to 120°C for 12 hours. The reaction mixture was poured into 200 mL of 1 .0 M hydrochloric acid and filtered to obtain a red solid.
- UV-vis(in toluene) A ma x (e [M- 1 crrv 1 ]): 495 nm (3.21 x 10 4 M- 1 crrv 1 ), 466 nm (2.45 x 10 4 M- 1 crrv 1 ).
- the monobrominated compound (also according to general formula II of the present invention)
- N-(1 -heptyloctyl)-8,1 1 -bis[4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-y]-perylene-3,4-dicarboxylic acid monoimide (1 .00 g, 1 .28 mmol) was suspended in a mixture of THF (90 ml), methanol (10 ml) and water (10 ml) in a 210 mL pressure vial . Copper(ll) bromide (2.85 g, 12.8 mmol) was added, the vessel sealed and heated up to 120°C for 12 hours. The reaction mixture was poured into 200 mL of 1 .0 M hydrochloric acid and filtered to obtain a red solid.
- N-(1 -ethylpropyl)-8,1 1 -bis[4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-y]-perylene-3,4-dicarboxylic acid monoimide (0.600 g, 0.933 mmol) was suspended in a mixture of dioxane (100 ml), methanol (10 ml) and water (10 ml) in a 210 mL pressure vial . Copper(ll) chloride (1 .254 g, 9.33 mmol) was added, the vessel sealed and heated up to 120°C for 12 hours. The reaction mixture was poured into 200 mL of 1 .0 M hydrochloric acid and filtered to obtain a red solid.
- UV-vis(in toluene) A max (e [M- crrr 1 ]): 494 nm (2.61 x 10 4 M- crrv 1 ), 465 nm (2.00 x 10 4 M- crrr 1 ).
- the monochlorinated compound (also according to general formula II of the present invention)
- IR spectrum (ATR) Amax [cm- 1 ] 3034, 2953, 2874, 2691 , 1652, 1593, 1566, 1500, 1457, 1349, 1268, 1246, 1 197, 1085, 808, 751 .
- IR spectrum (ATR) Amax [cm- 1 ] 2954, 2873, 1692, 1654, 1593, 1564, 1507, 1461 , 1351 , 1254, 1085, 1015, 805, 752.
- IR spectrum (ATR) Amax [cm- 1 ] 2951 , 2901 , 2871 , 1697, 1662, 1593, 1561 , 1506, 1365, 1250, 1 172, 1 132, 1013, 821 , 755.
- reaction mixture was purifed via gel permeation chromatography to separate mono- and difunctionalised product with chloroform and via column chromatography with dichloromethane. Yield: 50 mg brown solid (4 %) of compound C10.
- IR spectrum (ATR) Amax [cm- 1 ] 3630, 3499, 3058, 2957, 2923, 2860, 1750, 1691 , 1651 , 1591 , 1570, 1448, 1407, 1370, 1292, 1247, 1 172, 1073, 1020, 970, 853, 799, 755, 736.
- ⁇ ⁇ 2 blocking layer was prepared on a fluorine-doped tin oxide (FTO)-covered glass substrate using spray pyrolysis (cf. B. Peng, G. Jungmann, C. Jager, D. Haarer, H. W. Schmidt, M. Thelakkat, Coord. Chem. Rev. 2004, 248, 1479).
- a ⁇ 2 paste (Dyesol), diluted with terpineol, was applied by screen printing, resulting in a film thickness of 1.7 ⁇ .
- Fabrication of the device was completed by evaporation of 200 nm of silver as the counter electrode.
- the active area of the sDSC was defined by the size of these contacts (0.13 cm 2 ), and the cells were masked by an aperture of the same area for measurements.
- the current-voltage characteristics for all cells were measured with a Keithley 2400 under 1000 W/m 2 , AM 1 .5G conditions (LOT ORIEL 450 W).
- the incident photon to current conversion efficiency's (IPCE) were obtained with an Acton Research Monochromator using additional white background light illumination.
- the samples were illuminated with monochromatic light from the quartz monochromator with deuterium lamp.
- the power of the incident light beam was (2-5)-10 -8 W.
- the negative voltage of -300 V was supplied to the sample substrate.
- the counter-electrode with the 4.5x15 mm 2 slit for illumination was placed at 8 mm distance from the sample surface.
- the counter-electrode was connected to the input of the BK2-16 type electrometer, working in the open input regime, for the photocurrent measurement.
- the 10 "15 - 10 "12 A strong photocurrent was flowing in the circuit under illumination.
- the photocurrent J is strongly dependent on the incident light photon energy hv.
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- Power Engineering (AREA)
- Materials Engineering (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Photovoltaic Devices (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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EP13828249.6A EP2880018A4 (de) | 2012-08-06 | 2013-07-24 | Borhaltige perylenmonoimide, verfahren zu deren herstellung, deren verwendung als bausteine zur herstellung von perylenmonoimidderivaten, monoimidderivate und deren verwendung bei farbstoffsensibilisierten solarzellen |
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EP12179405 | 2012-08-06 | ||
PCT/IB2013/056070 WO2014024074A1 (en) | 2012-08-06 | 2013-07-24 | Boron containing perylene monoimides, process for their production, their use as building blocks for production of perylene monoimide derivatives, monoimide derivatives and their use in dye-sensitized solar cells |
EP13828249.6A EP2880018A4 (de) | 2012-08-06 | 2013-07-24 | Borhaltige perylenmonoimide, verfahren zu deren herstellung, deren verwendung als bausteine zur herstellung von perylenmonoimidderivaten, monoimidderivate und deren verwendung bei farbstoffsensibilisierten solarzellen |
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EP2880018A1 true EP2880018A1 (de) | 2015-06-10 |
EP2880018A4 EP2880018A4 (de) | 2016-01-13 |
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EP13828249.6A Withdrawn EP2880018A4 (de) | 2012-08-06 | 2013-07-24 | Borhaltige perylenmonoimide, verfahren zu deren herstellung, deren verwendung als bausteine zur herstellung von perylenmonoimidderivaten, monoimidderivate und deren verwendung bei farbstoffsensibilisierten solarzellen |
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EP (1) | EP2880018A4 (de) |
JP (1) | JP2015532638A (de) |
KR (1) | KR20150041069A (de) |
CN (1) | CN104520276A (de) |
AU (1) | AU2013301239A1 (de) |
WO (1) | WO2014024074A1 (de) |
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DE19701009A1 (de) * | 1997-01-14 | 1998-07-16 | Leonhard Feiler | Verfahren zur Herstellung von Perylen-3,4-dicarbonsäureanhydriden |
DE19700990A1 (de) * | 1997-01-14 | 1998-07-16 | Langhals Heinz | Die ausbalancierte Decarboxylierung von aromatischen Polycarbonsäuren - eine einstufige Synthese von Perylen-3,4-dicarbonsäureanhydrid |
DE19940708A1 (de) * | 1999-08-27 | 2001-03-01 | Basf Ag | Thermochrome Rylenfarbstoffe |
DE10243906A1 (de) * | 2002-09-20 | 2004-04-01 | Basf Ag | 9-Cyanosubstituierte Perylen-3,4-dicarbonsäuremonoimide |
DE102004054303A1 (de) * | 2004-11-09 | 2006-05-11 | Basf Ag | Verfahren zur Herstellung von Perylen-3,4-dicarbonsäureimiden |
US8119802B2 (en) * | 2007-04-24 | 2012-02-21 | Basf Aktiengesellschaft | Fluorinated dyes and their use in electrophoretic display devices |
EP2307507B1 (de) * | 2008-07-25 | 2016-04-20 | Basf Se | Neue azidsubstituierte naphthylen- oder rylenimid-derivate und ihre verwendung als reagentien in klick-reaktionen |
US20100022021A1 (en) * | 2008-07-25 | 2010-01-28 | Basf Se | New azide substituted naphthylene or rylene imide derivatives and their use as reagents in click-reactions |
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2013
- 2013-07-24 JP JP2015525968A patent/JP2015532638A/ja not_active Withdrawn
- 2013-07-24 KR KR20157005829A patent/KR20150041069A/ko not_active Application Discontinuation
- 2013-07-24 CN CN201380041568.1A patent/CN104520276A/zh active Pending
- 2013-07-24 WO PCT/IB2013/056070 patent/WO2014024074A1/en active Application Filing
- 2013-07-24 AU AU2013301239A patent/AU2013301239A1/en not_active Abandoned
- 2013-07-24 EP EP13828249.6A patent/EP2880018A4/de not_active Withdrawn
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CN104520276A (zh) | 2015-04-15 |
KR20150041069A (ko) | 2015-04-15 |
EP2880018A4 (de) | 2016-01-13 |
AU2013301239A1 (en) | 2015-02-05 |
JP2015532638A (ja) | 2015-11-12 |
WO2014024074A1 (en) | 2014-02-13 |
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