JP5778257B2 - 縮合チオフェンを製造する方法 - Google Patents
縮合チオフェンを製造する方法 Download PDFInfo
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- JP5778257B2 JP5778257B2 JP2013511225A JP2013511225A JP5778257B2 JP 5778257 B2 JP5778257 B2 JP 5778257B2 JP 2013511225 A JP2013511225 A JP 2013511225A JP 2013511225 A JP2013511225 A JP 2013511225A JP 5778257 B2 JP5778257 B2 JP 5778257B2
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- Prior art keywords
- thieno
- thiophene
- substituted
- formula
- compound
- Prior art date
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- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 title claims description 64
- 238000000034 method Methods 0.000 title claims description 57
- 229930192474 thiophene Natural products 0.000 title claims description 36
- 230000008569 process Effects 0.000 title claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 38
- -1 thiophene compound Chemical class 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 21
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical group COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000010949 copper Substances 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 7
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims description 6
- 239000005751 Copper oxide Substances 0.000 claims description 6
- 229910000431 copper oxide Inorganic materials 0.000 claims description 6
- 125000005257 alkyl acyl group Chemical group 0.000 claims description 5
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
- 239000000047 product Substances 0.000 description 27
- 239000007787 solid Substances 0.000 description 25
- 239000011541 reaction mixture Substances 0.000 description 22
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 125000000217 alkyl group Chemical group 0.000 description 15
- 238000006114 decarboxylation reaction Methods 0.000 description 15
- 229920000642 polymer Polymers 0.000 description 15
- 125000001424 substituent group Chemical group 0.000 description 15
- 125000001183 hydrocarbyl group Chemical group 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 229930195733 hydrocarbon Natural products 0.000 description 9
- 239000000178 monomer Substances 0.000 description 9
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 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 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- SXSRCDKIKPBDKB-UHFFFAOYSA-N 3,7-diheneicosylthieno[3,2-b]thieno[2',3':4,5]thieno[2,3-d]thiophene Chemical compound S1C=C(CCCCCCCCCCCCCCCCCCCCC)C2=C1C(SC1=C3SC=C1CCCCCCCCCCCCCCCCCCCCC)=C3S2 SXSRCDKIKPBDKB-UHFFFAOYSA-N 0.000 description 5
- PAJRNIZLXRSCGK-UHFFFAOYSA-N 5,12-di(heptadecyl)-3,7,10,14-tetrathiatetracyclo[6.6.0.02,6.09,13]tetradeca-1(8),2(6),4,9(13),11-pentaene Chemical compound S1C=C(CCCCCCCCCCCCCCCCC)C2=C1C(SC1=C3SC=C1CCCCCCCCCCCCCCCCC)=C3S2 PAJRNIZLXRSCGK-UHFFFAOYSA-N 0.000 description 5
- 125000005594 diketone group Chemical group 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- CWCKRNKYWPNOAZ-UHFFFAOYSA-N 2,3,5,6-tetrabromothieno[3,2-b]thiophene Chemical compound BrC1=C(Br)SC2=C1SC(Br)=C2Br CWCKRNKYWPNOAZ-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000004471 Glycine Substances 0.000 description 4
- 150000001204 N-oxides Chemical class 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 238000013459 approach Methods 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 230000005595 deprotonation Effects 0.000 description 4
- 238000010537 deprotonation reaction Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 150000003577 thiophenes Chemical class 0.000 description 4
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 238000006352 cycloaddition reaction Methods 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- PVBRSNZAOAJRKO-UHFFFAOYSA-N ethyl 2-sulfanylacetate Chemical compound CCOC(=O)CS PVBRSNZAOAJRKO-UHFFFAOYSA-N 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 125000000547 substituted alkyl group Chemical group 0.000 description 3
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 3
- 0 *C(c([s]c1c2[s]c(C(*)=O)c1Br)c2Br)=O Chemical compound *C(c([s]c1c2[s]c(C(*)=O)c1Br)c2Br)=O 0.000 description 2
- YIVYVVAAJAUESX-UHFFFAOYSA-N 1-(3,6-dibromo-5-octadecanoylthieno[3,2-b]thiophen-2-yl)octadecan-1-one Chemical compound BrC1=C(C(=O)CCCCCCCCCCCCCCCCC)SC2=C1SC(C(=O)CCCCCCCCCCCCCCCCC)=C2Br YIVYVVAAJAUESX-UHFFFAOYSA-N 0.000 description 2
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 2
- YMROWWUYEIGDPB-UHFFFAOYSA-N 2,6-dicarboethoxy-3,7-diheneicosylthieno[3,2-b]thieno[2',3':4,5]thieno[2,3-d]thiophene Chemical compound S1C(C(=O)OCC)=C(CCCCCCCCCCCCCCCCCCCCC)C2=C1C(SC1=C3SC(=C1CCCCCCCCCCCCCCCCCCCCC)C(=O)OCC)=C3S2 YMROWWUYEIGDPB-UHFFFAOYSA-N 0.000 description 2
- YDLAHBBJAGGIJZ-UHFFFAOYSA-N 2-sulfanylethyl acetate Chemical compound CC(=O)OCCS YDLAHBBJAGGIJZ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- VGWBXRXNERKBSJ-UHFFFAOYSA-N dithieno[2,3-a:2',3'-d]thiophene Chemical compound C1=CSC2=C1SC1=C2SC=C1 VGWBXRXNERKBSJ-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical class [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 229910052757 nitrogen Chemical group 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 125000005702 oxyalkylene group Chemical group 0.000 description 2
- 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 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 239000011669 selenium Chemical group 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 229910052714 tellurium Inorganic materials 0.000 description 2
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical group [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- XLOSTDKZSCUVKO-UHFFFAOYSA-N 1-(3,6-dibromo-5-docosanoylthieno[3,2-b]thiophen-2-yl)docosan-1-one Chemical compound BrC1=C(C(=O)CCCCCCCCCCCCCCCCCCCCC)SC2=C1SC(C(=O)CCCCCCCCCCCCCCCCCCCCC)=C2Br XLOSTDKZSCUVKO-UHFFFAOYSA-N 0.000 description 1
- FSXUMDFMZQSRJG-UHFFFAOYSA-N 1-(3,6-dibromo-5-undecanoylthieno[3,2-b]thiophen-2-yl)undecan-1-one Chemical compound BrC1=C(C(=O)CCCCCCCCCC)SC2=C1SC(C(=O)CCCCCCCCCC)=C2Br FSXUMDFMZQSRJG-UHFFFAOYSA-N 0.000 description 1
- BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 1
- CMQUQOHNANGDOR-UHFFFAOYSA-N 2,3-dibromo-4-(2,4-dibromo-5-hydroxyphenyl)phenol Chemical compound BrC1=C(Br)C(O)=CC=C1C1=CC(O)=C(Br)C=C1Br CMQUQOHNANGDOR-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- DSBPORXSYXZFHE-UHFFFAOYSA-N 3,7-didecanyl thieno[3,2-b]thieno[2',3':4,5]thieno[2,3-d]thiophene-2,6-dicarboxylic acid Chemical compound S1C(C(O)=O)=C(CCCCCCCCCC)C2=C1C(SC1=C3SC(=C1CCCCCCCCCC)C(O)=O)=C3S2 DSBPORXSYXZFHE-UHFFFAOYSA-N 0.000 description 1
- WDQMNRDIZZQPGE-UHFFFAOYSA-N 3,7-diheneicosyl thieno[3,2-b]thieno[2',3':4,5]thieno[2,3-d]thiophene-2,6-dicarboxylic acid Chemical compound S1C(C(O)=O)=C(CCCCCCCCCCCCCCCCCCCCC)C2=C1C(SC1=C3SC(=C1CCCCCCCCCCCCCCCCCCCCC)C(O)=O)=C3S2 WDQMNRDIZZQPGE-UHFFFAOYSA-N 0.000 description 1
- VFHPXBGDPYFNDM-UHFFFAOYSA-N 5,12-di(heptadecyl)-3,7,10,14-tetrathiatetracyclo[6.6.0.02,6.09,13]tetradeca-1(8),2(6),4,9(13),11-pentaene-4,11-dicarboxylic acid Chemical compound S1C(C(O)=O)=C(CCCCCCCCCCCCCCCCC)C2=C1C(SC1=C3SC(=C1CCCCCCCCCCCCCCCCC)C(O)=O)=C3S2 VFHPXBGDPYFNDM-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 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 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 239000003810 Jones reagent Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 230000008901 benefit 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
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000000306 component Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 1
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 1
- 229940112669 cuprous oxide Drugs 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 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 1
- 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 1
- 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 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([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
- 230000000911 decarboxylating effect Effects 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 238000001212 derivatisation Methods 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
- QTHQYNCAWSGBCE-UHFFFAOYSA-N docosanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCCCCCC(Cl)=O QTHQYNCAWSGBCE-UHFFFAOYSA-N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000011874 heated mixture Substances 0.000 description 1
- 125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920000140 heteropolymer Polymers 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 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 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 125000000743 hydrocarbylene group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 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
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 239000003471 mutagenic agent Substances 0.000 description 1
- 231100000707 mutagenic chemical Toxicity 0.000 description 1
- 230000003505 mutagenic effect Effects 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 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
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 229920001897 terpolymer Polymers 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
- 238000012360 testing method Methods 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- CHXZRHMQQRUVHF-UHFFFAOYSA-N thiophene A Natural products CC#CC1=CC=C(C#CC#CC=C)S1 CHXZRHMQQRUVHF-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- DOIRPCDOGSNNCS-UHFFFAOYSA-N trimethyl-[5-(5-trimethylstannylthiophen-2-yl)thiophen-2-yl]stannane Chemical compound S1C([Sn](C)(C)C)=CC=C1C1=CC=C([Sn](C)(C)C)S1 DOIRPCDOGSNNCS-UHFFFAOYSA-N 0.000 description 1
- JUKPJGZUFHCZQI-UHFFFAOYSA-N undecanoyl chloride Chemical compound CCCCCCCCCCC(Cl)=O JUKPJGZUFHCZQI-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- C07D495/22—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/782,055 US8217183B2 (en) | 2010-05-18 | 2010-05-18 | Methods of making fused thiophenes |
| US12/782,055 | 2010-05-18 | ||
| PCT/US2011/036180 WO2011146308A1 (en) | 2010-05-18 | 2011-05-12 | Methods of making fused thiophenes |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013533216A JP2013533216A (ja) | 2013-08-22 |
| JP2013533216A5 JP2013533216A5 (https=) | 2015-04-30 |
| JP5778257B2 true JP5778257B2 (ja) | 2015-09-16 |
Family
ID=44358164
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013511225A Expired - Fee Related JP5778257B2 (ja) | 2010-05-18 | 2011-05-12 | 縮合チオフェンを製造する方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8217183B2 (https=) |
| EP (1) | EP2571888B1 (https=) |
| JP (1) | JP5778257B2 (https=) |
| CN (1) | CN103025742B (https=) |
| TW (1) | TWI510493B (https=) |
| WO (1) | WO2011146308A1 (https=) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101694917B1 (ko) * | 2009-08-28 | 2017-01-23 | 에이전시 포 사이언스, 테크놀로지 앤드 리서치 | 폴리머 반도체, 소자 및 이를 제조하는 방법 |
| US8846855B2 (en) * | 2011-10-31 | 2014-09-30 | Corning Incorporated | Conjugated fused thiophenes, methods of making conjugated fused thiophenes, and uses thereof |
| US8901544B2 (en) | 2011-12-06 | 2014-12-02 | Corning Incorporated | Organic thin film transistor with ion exchanged glass substrate |
| CN103172646B (zh) * | 2011-12-22 | 2016-03-23 | 北京乐威泰克医药技术有限公司 | 一种新的烷基取代并多噻吩的合成方法 |
| WO2015035012A1 (en) | 2013-09-05 | 2015-03-12 | Corning Incorporated | Fused thiophene ditin monomers |
| JP6366728B2 (ja) | 2014-02-28 | 2018-08-01 | コーニング インコーポレイテッド | ジケトピロロピロール半導体材料、その調製方法およびその使用 |
| JP6337141B2 (ja) | 2014-11-25 | 2018-06-06 | 富士フイルム株式会社 | 有機半導体素子及びその製造方法、有機半導体組成物、有機半導体膜、化合物、並びに、オリゴマー又はポリマー |
| US9580556B2 (en) | 2015-01-29 | 2017-02-28 | Corning Incorporated | DPP with branched alkyl-chain or (and) fused thiophene with branched alkyl-chain and the related designing strategy to increase the molecular weight of their semi-conducting copolymers |
| US9761817B2 (en) | 2015-03-13 | 2017-09-12 | Corning Incorporated | Photo-patternable gate dielectrics for OFET |
| US9643978B2 (en) | 2015-04-29 | 2017-05-09 | Corning Incorporated | Methods and compounds for synthesizing fused thiophenes |
| KR20190057328A (ko) | 2016-09-16 | 2019-05-28 | 코닝 인코포레이티드 | 용융 티오펜-아릴티아디아졸 폴리머, 이러한 폴리머의 제조방법 및 그 사용방법 |
| CN111057087B (zh) * | 2019-11-01 | 2021-06-04 | 河南大学 | 一种非对称噻吩[7]螺烯同分异构体及其制备方法和应用 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10016723A1 (de) * | 2000-04-04 | 2001-10-11 | Bayer Ag | Verfahren zur Herstellung von Dialkoxythiophenen und Alkylendioxythiophenen |
| LT2896397T (lt) | 2003-08-01 | 2017-11-27 | Mitsubishi Tanabe Pharma Corporation | Nauji junginiai, turintys inhibitorinį aktyvumą prieš nuo natrio priklausomą gliukozės transporterį |
| US7838623B2 (en) | 2004-09-14 | 2010-11-23 | Corning Incorporated | Fused thiophenes, methods for making fused thiophenes, and uses thereof |
| KR101206202B1 (ko) * | 2004-09-14 | 2012-11-29 | 코닝 인코포레이티드 | 융합 티오펜, 융합 티오펜의 제조방법 및 그 용도 |
| JP4888043B2 (ja) | 2005-12-27 | 2012-02-29 | セイコーエプソン株式会社 | 有機半導体用組成物、トランジスタの製造方法、アクティブマトリクス装置の製造方法、電気光学装置の製造方法および電子機器の製造方法 |
| BRPI0707183A2 (pt) * | 2006-01-19 | 2011-04-26 | Athersys Inc | composto, composição farmacêutica, e, método de tratar uma doença, distúrbio e/ou condição em um paciente |
| JP2009256276A (ja) * | 2008-04-21 | 2009-11-05 | Tayca Corp | ３，４−アルキレンジオキシチオフェンの製造方法 |
| JP4239038B1 (ja) * | 2008-06-12 | 2009-03-18 | 東洋化成工業株式会社 | ジアルコキシチオフェンおよびアルキレンジオキシチオフェンの製造方法 |
| JP2010095469A (ja) * | 2008-10-16 | 2010-04-30 | Tama Kagaku Kogyo Kk | ３，４−ジアルコキシ（またはアルキレンジオキシ）チオフェンの製造方法 |
| CN101429189B (zh) * | 2008-12-24 | 2014-07-23 | 沈阳药科大学 | 2，3-二取代芳基噻吩类衍生物及其用途 |
| US7919634B2 (en) | 2009-05-28 | 2011-04-05 | Corning Incorporated | Fused thiophenes, articles, and methods thereof |
-
2010
- 2010-05-18 US US12/782,055 patent/US8217183B2/en active Active
-
2011
- 2011-05-12 EP EP11731558.0A patent/EP2571888B1/en not_active Not-in-force
- 2011-05-12 JP JP2013511225A patent/JP5778257B2/ja not_active Expired - Fee Related
- 2011-05-12 CN CN201180024452.8A patent/CN103025742B/zh active Active
- 2011-05-12 WO PCT/US2011/036180 patent/WO2011146308A1/en not_active Ceased
- 2011-05-12 TW TW100116584A patent/TWI510493B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| US8217183B2 (en) | 2012-07-10 |
| TW201219402A (en) | 2012-05-16 |
| US20110288306A1 (en) | 2011-11-24 |
| EP2571888A1 (en) | 2013-03-27 |
| EP2571888B1 (en) | 2014-12-31 |
| CN103025742B (zh) | 2015-09-09 |
| JP2013533216A (ja) | 2013-08-22 |
| TWI510493B (zh) | 2015-12-01 |
| WO2011146308A1 (en) | 2011-11-24 |
| CN103025742A (zh) | 2013-04-03 |
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