JP2015502920A - 共役縮合チオフェン、共役縮合チオフェンの製造方法、およびその使用 - Google Patents
共役縮合チオフェン、共役縮合チオフェンの製造方法、およびその使用 Download PDFInfo
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- JP2015502920A JP2015502920A JP2014539997A JP2014539997A JP2015502920A JP 2015502920 A JP2015502920 A JP 2015502920A JP 2014539997 A JP2014539997 A JP 2014539997A JP 2014539997 A JP2014539997 A JP 2014539997A JP 2015502920 A JP2015502920 A JP 2015502920A
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- Prior art keywords
- thiophene
- substituted
- moiety
- compound
- fused thiophene
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 45
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 title claims description 279
- 229930192474 thiophene Natural products 0.000 title claims description 92
- 230000008569 process Effects 0.000 title description 6
- 229920000642 polymer Polymers 0.000 claims abstract description 85
- 239000010409 thin film Substances 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 75
- 150000001875 compounds Chemical class 0.000 claims description 53
- 125000003118 aryl group Chemical group 0.000 claims description 46
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
- 239000000463 material Substances 0.000 claims description 20
- 238000005859 coupling reaction Methods 0.000 claims description 19
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 17
- 150000001299 aldehydes Chemical class 0.000 claims description 16
- 150000004820 halides Chemical class 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000000304 alkynyl group Chemical group 0.000 claims description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 14
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
- 150000001266 acyl halides Chemical class 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 230000008878 coupling Effects 0.000 claims description 11
- 238000010168 coupling process Methods 0.000 claims description 11
- 125000004001 thioalkyl group Chemical group 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 150000003573 thiols Chemical class 0.000 claims description 9
- 238000006555 catalytic reaction Methods 0.000 claims description 8
- 230000003287 optical effect Effects 0.000 claims description 8
- 230000005693 optoelectronics Effects 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 239000004020 conductor Substances 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 239000004065 semiconductor Substances 0.000 claims description 4
- 229940126214 compound 3 Drugs 0.000 claims description 2
- 239000000203 mixture Substances 0.000 abstract description 134
- -1 heterocyclic organic compounds Chemical class 0.000 abstract description 47
- 150000003577 thiophenes Chemical class 0.000 abstract description 21
- 239000000178 monomer Substances 0.000 abstract description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 142
- 238000006243 chemical reaction Methods 0.000 description 90
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
- 239000007787 solid Substances 0.000 description 47
- 239000000243 solution Substances 0.000 description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 37
- 238000005481 NMR spectroscopy Methods 0.000 description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
- 239000012044 organic layer Substances 0.000 description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 239000002904 solvent Substances 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 238000001704 evaporation Methods 0.000 description 21
- 238000003786 synthesis reaction Methods 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 18
- 239000012267 brine Substances 0.000 description 18
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 18
- 238000001914 filtration Methods 0.000 description 18
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 230000008020 evaporation Effects 0.000 description 16
- 239000003054 catalyst Substances 0.000 description 15
- 239000001257 hydrogen Substances 0.000 description 15
- 229910052739 hydrogen Inorganic materials 0.000 description 15
- 229920001577 copolymer Polymers 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 12
- 238000004440 column chromatography Methods 0.000 description 12
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 12
- 239000012043 crude product Substances 0.000 description 11
- 125000004122 cyclic group Chemical group 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 238000007363 ring formation reaction Methods 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 11
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 10
- 229910004298 SiO 2 Inorganic materials 0.000 description 10
- 239000011541 reaction mixture 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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 229920000547 conjugated polymer Polymers 0.000 description 9
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 9
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 230000009102 absorption Effects 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 8
- 239000012300 argon atmosphere Substances 0.000 description 8
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 8
- 150000007942 carboxylates Chemical class 0.000 description 7
- 230000003197 catalytic effect Effects 0.000 description 7
- 229920001519 homopolymer Polymers 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- 125000000547 substituted alkyl group Chemical group 0.000 description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000000539 dimer Substances 0.000 description 6
- 125000002950 monocyclic group Chemical group 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 125000003396 thiol group Chemical group [H]S* 0.000 description 6
- BPQKNKPCFXFUER-UHFFFAOYSA-N 3,6-didecylthieno[3,2-b]thiophene Chemical compound CCCCCCCCCCC1=CSC2=C1SC=C2CCCCCCCCCC BPQKNKPCFXFUER-UHFFFAOYSA-N 0.000 description 5
- CETNYQUTSDGGKV-UHFFFAOYSA-N 3,6-dihexylthieno[3,2-b]thiophene Chemical compound CCCCCCC1=CSC2=C1SC=C2CCCCCC CETNYQUTSDGGKV-UHFFFAOYSA-N 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- KWTSZCJMWHGPOS-UHFFFAOYSA-M chloro(trimethyl)stannane Chemical compound C[Sn](C)(C)Cl KWTSZCJMWHGPOS-UHFFFAOYSA-M 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- PVBRSNZAOAJRKO-UHFFFAOYSA-N ethyl 2-sulfanylacetate Chemical compound CCOC(=O)CS PVBRSNZAOAJRKO-UHFFFAOYSA-N 0.000 description 5
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- 125000003367 polycyclic group Chemical group 0.000 description 5
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 5
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 4
- WYFCZWSWFGJODV-MIANJLSGSA-N 4-[[(1s)-2-[(e)-3-[3-chloro-2-fluoro-6-(tetrazol-1-yl)phenyl]prop-2-enoyl]-5-(4-methyl-2-oxopiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-1-carbonyl]amino]benzoic acid Chemical compound O=C1CN(C)CCN1C1=CC=CC2=C1CCN(C(=O)\C=C\C=1C(=CC=C(Cl)C=1F)N1N=NN=C1)[C@@H]2C(=O)NC1=CC=C(C(O)=O)C=C1 WYFCZWSWFGJODV-MIANJLSGSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 238000005917 acylation reaction Methods 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- YQUSJUJNDKUWAM-UHFFFAOYSA-N benzenesulfonylsulfanylsulfonylbenzene Chemical compound C=1C=CC=CC=1S(=O)(=O)SS(=O)(=O)C1=CC=CC=C1 YQUSJUJNDKUWAM-UHFFFAOYSA-N 0.000 description 4
- VGWBXRXNERKBSJ-UHFFFAOYSA-N dithieno[2,3-a:2',3'-d]thiophene Chemical compound C1=CSC2=C1SC1=C2SC=C1 VGWBXRXNERKBSJ-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- KMPQYAYAQWNLME-UHFFFAOYSA-N undecanal Chemical compound CCCCCCCCCCC=O KMPQYAYAQWNLME-UHFFFAOYSA-N 0.000 description 4
- 229910000634 wood's metal Inorganic materials 0.000 description 4
- GCTFTMWXZFLTRR-GFCCVEGCSA-N (2r)-2-amino-n-[3-(difluoromethoxy)-4-(1,3-oxazol-5-yl)phenyl]-4-methylpentanamide Chemical compound FC(F)OC1=CC(NC(=O)[C@H](N)CC(C)C)=CC=C1C1=CN=CO1 GCTFTMWXZFLTRR-GFCCVEGCSA-N 0.000 description 3
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- AHUQRGHAKJSUKU-UHFFFAOYSA-N 1,4-bis[5-(1-benzofuran-2-yl)thiophen-2-yl]-2,5-bis(2-ethylhexyl)pyrrolo[3,4-c]pyrrole-3,6-dione Chemical compound C1=CC=C2OC(C3=CC=C(S3)C3=C4C(=O)N(C(=C4C(=O)N3CC(CC)CCCC)C=3SC(=CC=3)C=3OC4=CC=CC=C4C=3)CC(CC)CCCC)=CC2=C1 AHUQRGHAKJSUKU-UHFFFAOYSA-N 0.000 description 3
- FEWLNYSYJNLUOO-UHFFFAOYSA-N 1-Piperidinecarboxaldehyde Chemical compound O=CN1CCCCC1 FEWLNYSYJNLUOO-UHFFFAOYSA-N 0.000 description 3
- QXOGPTXQGKQSJT-UHFFFAOYSA-N 1-amino-4-[4-(3,4-dimethylphenyl)sulfanylanilino]-9,10-dioxoanthracene-2-sulfonic acid Chemical compound Cc1ccc(Sc2ccc(Nc3cc(c(N)c4C(=O)c5ccccc5C(=O)c34)S(O)(=O)=O)cc2)cc1C QXOGPTXQGKQSJT-UHFFFAOYSA-N 0.000 description 3
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 3
- LYFAOCDBRNVBOO-UHFFFAOYSA-N 2-bromo-3 -decanyldithieno[2,3-d:2',3'-d']thieno[3,2-b:4,5-b']dithiophene Chemical compound C1=CSC2=C1SC1=C2SC2=C1SC1=C2SC(Br)=C1CCCCCCCCCC LYFAOCDBRNVBOO-UHFFFAOYSA-N 0.000 description 3
- ZGXLLWNCBNQEEY-UHFFFAOYSA-N 2-dec-1-ynyl-3-decanyldithieno[2,3-d:2',3'-d']thieno [3,2-b:4,5-b']dithiophene Chemical compound C1=CSC2=C1SC1=C2SC2=C1SC1=C2SC(C#CCCCCCCCC)=C1CCCCCCCCCC ZGXLLWNCBNQEEY-UHFFFAOYSA-N 0.000 description 3
- FGTPHFGZGZOZGD-UHFFFAOYSA-N 2-thiophen-2-ylsulfanylacetic acid Chemical group OC(=O)CSC1=CC=CS1 FGTPHFGZGZOZGD-UHFFFAOYSA-N 0.000 description 3
- BDXLSXMWSHQOJG-UHFFFAOYSA-N 3,7-didecylthieno[3,2-b]thieno[2',3':4,5]thieno[2,3-d]thiophene Chemical compound S1C=C(CCCCCCCCCC)C2=C1C(SC1=C3SC=C1CCCCCCCCCC)=C3S2 BDXLSXMWSHQOJG-UHFFFAOYSA-N 0.000 description 3
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- YVXDRBKJBITUIY-UHFFFAOYSA-N 3-decyl-6-dec-1-ynyldithieno[2,3-a:3',2'-c]thiophene Chemical compound C1=C(C#CCCCCCCCC)SC2=C1SC1=C2SC=C1CCCCCCCCCC YVXDRBKJBITUIY-UHFFFAOYSA-N 0.000 description 3
- JEDHEMYZURJGRQ-UHFFFAOYSA-N 3-hexylthiophene Chemical compound CCCCCCC=1C=CSC=1 JEDHEMYZURJGRQ-UHFFFAOYSA-N 0.000 description 3
- GHEXCMCZELTYSX-UHFFFAOYSA-N 5,6-didecyldithieno[2,3-a:3',2'-c]thiophene Chemical compound C1=CSC2=C1SC1=C2SC(CCCCCCCCCC)=C1CCCCCCCCCC GHEXCMCZELTYSX-UHFFFAOYSA-N 0.000 description 3
- HNSPPNCMIVKRKY-UHFFFAOYSA-N 5-bromo-3-decyldithieno[3,2-c:2',3'-e]thiophene Chemical compound BrC1=CSC2=C1SC1=C2SC=C1CCCCCCCCCC HNSPPNCMIVKRKY-UHFFFAOYSA-N 0.000 description 3
- SHSOKZVOFYPWEA-UHFFFAOYSA-N 5-bromo-3-decyldithieno[3,2-c:4',3'-e]thiophene-6-carbaldehyde Chemical compound BrC1=C(C=O)SC2=C1SC1=C2SC=C1CCCCCCCCCC SHSOKZVOFYPWEA-UHFFFAOYSA-N 0.000 description 3
- FIANFYAFSODZOV-UHFFFAOYSA-N 6-bromo-5-decyldithieno[2,3-a:4',3'-c]thiophene Chemical compound C1=CSC2=C1SC1=C2SC(Br)=C1CCCCCCCCCC FIANFYAFSODZOV-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 3
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 3
- 229940125900 compound 59 Drugs 0.000 description 3
- 238000010276 construction Methods 0.000 description 3
- 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 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000002704 decyl 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])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 229940043279 diisopropylamine Drugs 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000007789 sealing Methods 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
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- XFJBGINZIMNZBW-CRAIPNDOSA-N 5-chloro-2-[4-[(1r,2s)-2-[2-(5-methylsulfonylpyridin-2-yl)oxyethyl]cyclopropyl]piperidin-1-yl]pyrimidine Chemical compound N1=CC(S(=O)(=O)C)=CC=C1OCC[C@H]1[C@@H](C2CCN(CC2)C=2N=CC(Cl)=CN=2)C1 XFJBGINZIMNZBW-CRAIPNDOSA-N 0.000 description 1
- IOCMCNSQCJLUBK-UHFFFAOYSA-N 6-bromo-3-hexylthieno[3,2-b]thiophene Chemical compound BrC1=CSC2=C1SC=C2CCCCCC IOCMCNSQCJLUBK-UHFFFAOYSA-N 0.000 description 1
- MUTOZPCYGLLBNK-UHFFFAOYSA-N 6-hexylthieno[3,2-b]thiophene-5-carboxylic acid Chemical compound C1=CSC2=C1SC(C(O)=O)=C2CCCCCC MUTOZPCYGLLBNK-UHFFFAOYSA-N 0.000 description 1
- HCCNBKFJYUWLEX-UHFFFAOYSA-N 7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)-3-(pyrazin-2-ylmethylamino)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCC1=CN=CC=N1 HCCNBKFJYUWLEX-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- JQUCWIWWWKZNCS-LESHARBVSA-N C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F Chemical compound C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F JQUCWIWWWKZNCS-LESHARBVSA-N 0.000 description 1
- JNVQLSSKFYUFGQ-UHFFFAOYSA-N C(CCCCC)C=1C2=C(SC1)C(=CS2)CCCCCC.S2C1=C(C=C2)SC=C1 Chemical class C(CCCCC)C=1C2=C(SC1)C(=CS2)CCCCCC.S2C1=C(C=C2)SC=C1 JNVQLSSKFYUFGQ-UHFFFAOYSA-N 0.000 description 1
- PPCNIALSOQSZCT-UHFFFAOYSA-N C(CCCCC)C=1C2=C(SC1)C=CS2.S2C1=C(C=C2)SC=C1 Chemical class C(CCCCC)C=1C2=C(SC1)C=CS2.S2C1=C(C=C2)SC=C1 PPCNIALSOQSZCT-UHFFFAOYSA-N 0.000 description 1
- WMRYZAKYOSWUMF-UHFFFAOYSA-N C(CCCCCCCCC)C1=CSC2=C1SC1=C2SC2=C1SC=C2CCCCCCCCCC.S2C=CC=1SC3=C(C12)SC1=C3SC=C1 Chemical class C(CCCCCCCCC)C1=CSC2=C1SC1=C2SC2=C1SC=C2CCCCCCCCCC.S2C=CC=1SC3=C(C12)SC1=C3SC=C1 WMRYZAKYOSWUMF-UHFFFAOYSA-N 0.000 description 1
- NGUWGQGRSJGQFL-UHFFFAOYSA-N CCCCCCCCCC(C(SC1=C2[S+](C(CCCCCCCCC)O)C=C1Br)=C2Br)O Chemical compound CCCCCCCCCC(C(SC1=C2[S+](C(CCCCCCCCC)O)C=C1Br)=C2Br)O NGUWGQGRSJGQFL-UHFFFAOYSA-N 0.000 description 1
- JPVRHHYQENCVEO-UHFFFAOYSA-N CCCCCCCCCCC1=CSC(C2=C3C(SC(Br)=C4CCCCCCCCCC)=C4S2)=C1[S+]3Br Chemical compound CCCCCCCCCCC1=CSC(C2=C3C(SC(Br)=C4CCCCCCCCCC)=C4S2)=C1[S+]3Br JPVRHHYQENCVEO-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Chemical group 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical class [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- LVDRREOUMKACNJ-BKMJKUGQSA-N N-[(2R,3S)-2-(4-chlorophenyl)-1-(1,4-dimethyl-2-oxoquinolin-7-yl)-6-oxopiperidin-3-yl]-2-methylpropane-1-sulfonamide Chemical compound CC(C)CS(=O)(=O)N[C@H]1CCC(=O)N([C@@H]1c1ccc(Cl)cc1)c1ccc2c(C)cc(=O)n(C)c2c1 LVDRREOUMKACNJ-BKMJKUGQSA-N 0.000 description 1
- QOVYHDHLFPKQQG-NDEPHWFRSA-N N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O Chemical compound N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O QOVYHDHLFPKQQG-NDEPHWFRSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- ZQRGREQWCRSUCI-UHFFFAOYSA-N [S].C=1C=CSC=1 Chemical compound [S].C=1C=CSC=1 ZQRGREQWCRSUCI-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001347 alkyl bromides Chemical class 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
- 238000013459 approach Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940126545 compound 53 Drugs 0.000 description 1
- 229940127113 compound 57 Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- LBJNMUFDOHXDFG-UHFFFAOYSA-N copper;hydrate Chemical class O.[Cu].[Cu] LBJNMUFDOHXDFG-UHFFFAOYSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000007256 debromination reaction Methods 0.000 description 1
- ZBQUMMFUJLOTQC-UHFFFAOYSA-L dichloronickel;3-diphenylphosphanylpropyl(diphenyl)phosphane Chemical compound Cl[Ni]Cl.C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 ZBQUMMFUJLOTQC-UHFFFAOYSA-L 0.000 description 1
- LNPMYFRCGOZOPT-UHFFFAOYSA-N diethyl 3,5-didecyldithieno[4,3-d:4',3'-e]thiophene-2,6-dicarboxylate Chemical compound CCCCCCCCCCC1=C(C(=O)OCC)SC2=C1SC1=C2SC(C(=O)OCC)=C1CCCCCCCCCC LNPMYFRCGOZOPT-UHFFFAOYSA-N 0.000 description 1
- KVWNCEHYFKPSGJ-UHFFFAOYSA-N diethyl 3,7-didecylthieno[3,2-b]thieno[2',3':4,5]thieno[2,3-d]thiophene 2,6-dicarboxylate Chemical compound S1C(C(=O)OCC)=C(CCCCCCCCCC)C2=C1C(SC1=C3SC(=C1CCCCCCCCCC)C(=O)OCC)=C3S2 KVWNCEHYFKPSGJ-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- MXTGSJWIWTXARD-UHFFFAOYSA-N dithieno[3,2-b:3',2'-e]thiophene 4,4-dioxide Chemical class S1C=CC2=C1C(SC=C1)=C1S2(=O)=O MXTGSJWIWTXARD-UHFFFAOYSA-N 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- HFTNNOZFRQLFQB-UHFFFAOYSA-N ethenoxy(trimethyl)silane Chemical compound C[Si](C)(C)OC=C HFTNNOZFRQLFQB-UHFFFAOYSA-N 0.000 description 1
- RJUAFOGEESYKBX-UHFFFAOYSA-N ethyl 6-hexylthieno[3,2-b]thiophene-5-carboxylate Chemical compound C1=CSC2=C1SC(C(=O)OCC)=C2CCCCCC RJUAFOGEESYKBX-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- LZKLAOYSENRNKR-LNTINUHCSA-N iron;(z)-4-oxoniumylidenepent-2-en-2-olate Chemical compound [Fe].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O LZKLAOYSENRNKR-LNTINUHCSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- 239000000382 optic material Substances 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002734 organomagnesium group Chemical group 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- NBFBORAIBRIYGM-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione;thiophene Chemical group C=1C=CSC=1.C1=CN=C2C(=O)C(=O)N=C21 NBFBORAIBRIYGM-UHFFFAOYSA-N 0.000 description 1
- QKWILNTYPDJSME-UHFFFAOYSA-N pyrrolo[3,4-c]pyrrole-3,6-dione Chemical compound C1=NC(=O)C2=C1C(=O)N=C2 QKWILNTYPDJSME-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000005266 side chain polymer Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- CAUONNQGFXOEMY-UHFFFAOYSA-N tributyl(2-tributylstannylethynyl)stannane Chemical group CCCC[Sn](CCCC)(CCCC)C#C[Sn](CCCC)(CCCC)CCCC CAUONNQGFXOEMY-UHFFFAOYSA-N 0.000 description 1
- VNKOWRBFAJTPLS-UHFFFAOYSA-N tributyl-[(z)-2-tributylstannylethenyl]stannane Chemical group CCCC[Sn](CCCC)(CCCC)\C=C\[Sn](CCCC)(CCCC)CCCC VNKOWRBFAJTPLS-UHFFFAOYSA-N 0.000 description 1
- GPZGAMSKANHWHO-UHFFFAOYSA-N trimethyl-(4-trimethylstannylphenyl)stannane Chemical compound C[Sn](C)(C)C1=CC=C([Sn](C)(C)C)C=C1 GPZGAMSKANHWHO-UHFFFAOYSA-N 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/06—Polythioethers from cyclic thioethers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/151—Copolymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
- C08G2261/141—Side-chains having aliphatic units
- C08G2261/1412—Saturated aliphatic units
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/22—Molecular weight
- C08G2261/226—Oligomers, i.e. up to 10 repeat units
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
- C08G2261/3223—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
-
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Abstract
Description
(i)α−ヒドロ−β−ブロモチオフェン部分を提供する工程、
(ii)このα−ヒドロ−β−ブロモチオフェン部分を、このチオフェン部分をα位置で、Rが少なくとも4つの炭素を有するアルキル基であるR−アシル部分によりアシル化することによって、α−(R−アシル)−β−カルボキシメチルチオチオフェン部分に転化する工程、
(iii)β−ブロミドを2−メルカプトアセテートで置換する工程、
(iv)α−(R−アシル)−β−カルボキシメチルチオチオフェン部分を環化させて、α”−カルボキシ−β”−R−置換縮合チオフェン部分を形成する工程、および
(v)このα”−カルボキシ−β”−R−置換縮合チオフェン部分からカルボキシレートを除去して、β”−R−置換縮合チオフェン部分を形成する工程、
を有してなる。
図10の反応スキームに示されるように、3,6−ジヘキシルチエノ[3,2−b]チオフェン57を合成する。
図11の反応スキームに示されるように、3−ヘキシルチエノ[3,2−b]チオフェン58を合成する。
3,6−ジデシルチエノ[3,2−b]チオフェン63および3,6−ジデシルチエノ[3,2−b]チオフェン−4,4−ジオキシド64を、図12の反応スキームに示されたように合成する。
3,7−ジデシルチエノ[3,2−b]チエノ[2’,3’:4,5]チエノ[2,3−d]チオフェン70を、図13の反応スキームに示されるように合成する。
β−ヘキシル置換チエノ[2,3−d]チオフェンを合成するうまくいかなかった試みにおいて、図14の反応スキームにしたがう。縮合環系の電子的性質は、単純な単環式チオフェンのものとは大きく異なるので、単環式チオフェンに使用したカップリング反応は機能しない。
以下に説明する一般に手法を使用して、縮合チオフェンポリマーを製造する。この手法は、ここに引用する、Andersson et al., 27 MACROMOLECULES 6506 (1994)から適用される。
2−2、3−3および4−4二量体並びに5および7環系の合成が、図15に示されている。
3環および4環のテトラアルキル置換チエノチオフェン二量体の合成が、それぞれ、図16および17に示されている。
2−ブロモ−3−デカニルジチエノ[3,2−b:2’,3’−d]チオフェン(92)。 3−デカニルジチエノ[3,2−b:2’,3’−d]チオフェン(91)(9.03g、0.027モル)をDMF(100mL)中に溶解させた。この溶液に、暗所において、アルゴン雰囲気下で、DMF(50mL)中のN−ブロモスクシンイミド(NBS)(4.78g、0.027モル)を滴下した。得られた混合物を、約3時間に亘り、またはGC/MSが415に単峰を示すまで、0℃で撹拌した。この溶液を水(500mL)中に注ぎ入れ、有機溶液をヘキサン(3×100mL)で抽出した。混合有機溶液を塩水(2×50mL)と水(50mL)で洗浄した。MgSO4での乾燥後、ヘキサンを蒸発させた。粗製生成物をカラム・クロマトグラフィーにより精製し、ヘキサンで溶出して、目的の化合物(10.1g、収率90.2%)を生成した。1HNMR (CD2Cl2): δ 7.39 (d, 1H), 7.29 (d, 1H), 2.74 (t, 2H), 1.74-1.33 (m, 16H), 0.89 (t, 3H). 13CNMR: 140.89, 140.63, 136.00, 131.55, 129.22, 126.58, 121.04, 108.89, 32.31, 29.94, 29.73 (重複), 29.35, 28.49, 23.09, 14.27。
2−ホルミル−3−ブロモ−5−デカニルジチエノ[3,2−b:2’,3’−d]チオフェン(102)。 ブチルリチウム(ヘキサン中2.5M、10.9mL、0.0273モル)を、乾燥THF(100mL)中のジイソプロピルアミン(2.76g、0.027モル)が入ったフラスコに0℃で滴下した。得られた混合物を15分間に亘り0℃に保持した。3−ブロモ−5−デカニル−ジチエノ[3,2−b:2’,3’−d]チオフェン(101)(11.33g、0.0273モル)をTHF(60mL)中に溶解させ、この反応溶液に滴下した。この混合物を1時間に亘り0℃に保持し、その後、1−ホルミルピペリジンを添加した。得られた混合物を一晩撹拌し、次いで、THFを除去した。残留物を10%の塩化水素酸(30mL)および水(3×100mL)で洗浄した。目的の固体化合物をエチルアルコール(100mL)からの結晶化により精製した(8.80g、収率72.8%)。m.p. 65.5-67.2 ℃。
ポリ−3,6−ジヘキシル−チエノ[3,2−b]チオフェン(PDC6FT2)およびポリ−3,6−ジデカニル−チエノ[3,2−b]チオフェン(PDC10FT2)。
2,3−ジブロモ−3,5−ジデカニルジチエノ[3,2−b;2’,3’−d]チオフェン(1.0g、1.57ミリモル)、2,5’−ジスタンニルトリメチル−ビチオフェン(0.772g、1.57ミリモル)およびテトラキス(トリフェニルホスフィン)パラジウム(0)(0.095g、0.082ミリモル)をアルゴン雰囲気下でクロロベンゼン(30mL)中に溶解させる。得られた混合物を14時間に亘りアルゴン雰囲気下で150℃に加熱し、その後、メタノール(400mL)中に沈殿させる。収集した固体ポリマーをアセトン(100mL)で洗浄し、ソックスレー抽出器内でアセトンを使用して抽出する。次いで、固体ポリマーをクロロベンゼン(100mL)中に溶解させ、ガラスフィルタに通して濾過する。クロロベンゼンのほとんどを蒸発させた後、下記に示されるポリマーをメタノール(300mL)から再び沈殿させる。赤色のポリマー粉末を真空下で乾燥させて、0.9グラム(収率90.1%)を生成する。
ジケトピロロピロール(「DPP」)部分をさらに含むポリマーに縮合チオフェン部分を含ませることには、いくつかの利点がある:1)縮合チオフェン部分にβ−水素がないために、DPP共役コポリマー構造がより安定になるであろう;2)縮合チオフェン部分に大きいアルキル系のR基を配置する可能性により、コポリマーの溶解度を改善することができる;3)縮合チオフェン系は大きい共役単位からなり、これにより、DPP系の電子的性質および光学的性質が改善されるであろう。
, 2.68; N, 9.33; S, 21.35。
ポリ[(3,7−ジヘプタデシルチエノ[3,2−b]チエノ[2’,3’:4,5]チエノ[2,3−d]チオフェン−2,6−ジイル)(アセチレン−1,2−ジイル)](「PTrDC17FT4」)(図25)− 2,6−ジブロモ−3,7−ジヘプタデシルチエノ[3,2−b]チエノ[2’,3’:4,5]チエノ[2,3−d]チオフェン(0.41g、0.46ミリモル)およびビス(トリブチルスタンニル)アセチレン(0.28g、0.462ミリモル)を、撹拌子を備えた三口フラスコに移した。数分間に亘りこのフラスコに窒素を通して泡立てた。フラスコを密封した後、これをグローブボックス内に入れた。このフラスコに、0.027g(0.023ミリモル)のPd(PPh3)4および24mLの無水トルエンと6mLの酢酸n−ブチルの混合溶媒を加えた。このフラスコを16時間に亘り窒素雰囲気下で約130℃で加熱し、その後、メタノール(200mL)中に注ぎ入れた。この混合物を室温で一晩撹拌した。沈殿物を濾過し、ソックスレー装置において、最初に24時間に亘りメタノールで、次いで、24時間に亘りアセトンで抽出した。収集したポリマーを真空下で乾燥させて、0.18グラムの濃い色のポリマーを生成し、ポリ[(3,7−ジヘプタデシルチエノ[3,2−b]チエノ[2’,3’:4,5]チエノ[2,3−d]チオフェン−2,6−ジイル)(アセチレン−1,2−ジイル)]と特定された。
Claims (12)
- 式100または101:
を有する化合物であって、式中、a、m、およびnは、独立して、1以上の整数であり;
各Xは、独立して共役基を含み、a=1の場合、Xはアリールではなく、a>1の場合、全てのXがアリールであるわけではなく;
R1およびR2は、独立して、置換または未置換のアルキル、置換または未置換のアルケニル、置換または未置換のアルキニル、アリール、置換または未置換のシクロアルキル、アラルキル、アミノ、エステル、アルデヒド、ヒドロキシル、アルコキシ、チオール、チオアルキル、ハロゲン化物、アシルハロゲン化物、アクリレート、またはビニルエーテルである、化合物。 - R1およびR2の少なくとも一方が、置換または未置換のアルキルを含む、請求項1記載の化合物。
- R1およびR2の少なくとも一方が、未置換のアルキルを含む、請求項2記載の化合物。
- aが2以上であり、Xが、共役アルケニルまたはアルキニルもしくはアリールを含む、請求項1から3いずれか1項記載の化合物。
- m>1である共役縮合チオフェンポリマーまたはオリゴマーに含まれる、請求項1から4いずれか1項記載の化合物。
- nが1から15である、請求項1から5いずれか1項記載の化合物。
- 請求項1から6いずれか1項記載の化合物を含むポリマーであって、約400から約1800Daの分子量を有するポリマー。
- 電子装置、光電子工学装置、または非線形光学装置に構成された、請求項1から6記載の化合物を含む装置。
- トランジスタ(FET)、薄膜トランジスタ(TFT)、有機発光ダイオード(OLED)、電子光学(EO)装置、導電材料、二光子混合材料、有機半導体、RFIDタグ、エレクトロルミネセント装置、または光起電装置とセンサ装置を含む、請求項8記載の装置。
- 請求項1から6いずれか1項記載の化合物を製造する方法において、
(i)構造1または2:
の縮合チオフェン部分であって、
R1およびR2は、独立して、置換または未置換のアルキル、置換または未置換のアルケニル、置換または未置換のアルキニル、アリール、置換または未置換のシクロアルキル、アラルキル、アミノ、エステル、アルデヒド、ヒドロキシル、アルコキシ、チオール、チオアルキル、ハロゲン化物、アシルハロゲン化物、アクリレート、またはビニルエーテルであり;
XおよびYは、独立して、ハロゲン化物またはSn(Alk)3であり、Alkは、置換または未置換のアルキルもしくは置換または未置換のシクロアルキルである、縮合チオフェン部分を提供する工程;
(ii)構造3または4:
のビス置換された共役部分であって、
Zは、1つ以上のアリールのみからなるものではない共役基であり、Haはハロゲンであり、Alkは、置換または未置換のアルキルもしくは置換または未置換のシクロアルキルである、共役部分を提供する工程;および
(iii)触媒反応により、構造1または2の前記縮合チオフェン部分を、構造3または4の前記共役部分とカップリングさせる工程であって、XおよびYがハロゲンであるときに化合物3が使用され、XおよびYがSn(Alk)3であるときに化合物4が使用される、工程、
を有してなる方法。 - 前記触媒反応が金属触媒反応である、請求項10記載の方法。
- 前記金属触媒反応が、スティル・タイプのカップリングである、請求項11記載の方法。
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- 2012-10-26 CN CN201280053264.2A patent/CN104093723A/zh active Pending
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- 2012-10-26 EP EP12845556.5A patent/EP2773646B1/en not_active Not-in-force
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EP2773646A1 (en) | 2014-09-10 |
KR20140094586A (ko) | 2014-07-30 |
EP2773646A4 (en) | 2015-04-29 |
US20130109821A1 (en) | 2013-05-02 |
CN108250414A (zh) | 2018-07-06 |
CN104093723A (zh) | 2014-10-08 |
EP2773646B1 (en) | 2016-06-15 |
US8846855B2 (en) | 2014-09-30 |
WO2013066732A1 (en) | 2013-05-10 |
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