TWI510493B - 製造稠合噻吩之方法 - Google Patents
製造稠合噻吩之方法 Download PDFInfo
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- TWI510493B TWI510493B TW100116584A TW100116584A TWI510493B TW I510493 B TWI510493 B TW I510493B TW 100116584 A TW100116584 A TW 100116584A TW 100116584 A TW100116584 A TW 100116584A TW I510493 B TWI510493 B TW I510493B
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- Prior art keywords
- thiophene
- thieno
- substituted
- formula
- group
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- 238000000034 method Methods 0.000 title claims description 52
- 229930192474 thiophene Natural products 0.000 title claims description 43
- 150000003577 thiophenes Chemical class 0.000 title description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 74
- -1 thiophene compound Chemical class 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 27
- 230000008569 process Effects 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 14
- 238000006114 decarboxylation reaction Methods 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 11
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical group COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims description 5
- 239000005751 Copper oxide Substances 0.000 claims description 5
- 239000004471 Glycine Substances 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 239000010949 copper Substances 0.000 claims description 5
- 229910000431 copper oxide Inorganic materials 0.000 claims description 5
- 238000010511 deprotection reaction Methods 0.000 claims description 5
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 claims description 5
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 2
- 150000001413 amino acids Chemical class 0.000 claims 2
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims 1
- 125000000743 hydrocarbylene group Chemical group 0.000 claims 1
- 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 32
- 239000000047 product Substances 0.000 description 31
- 239000007787 solid Substances 0.000 description 25
- 239000011541 reaction mixture Substances 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 125000000217 alkyl group Chemical group 0.000 description 14
- 229920000642 polymer Polymers 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- 229930195733 hydrocarbon Natural products 0.000 description 13
- 125000001424 substituent group Chemical group 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 11
- 238000009472 formulation Methods 0.000 description 11
- 239000007789 gas Substances 0.000 description 9
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 125000005594 diketone group Chemical group 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000007363 ring formation reaction Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 150000001204 N-oxides Chemical class 0.000 description 4
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 4
- 238000005034 decoration Methods 0.000 description 4
- 238000006471 dimerization reaction Methods 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 3
- 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 3
- CPZZNABEJQWLJM-UHFFFAOYSA-N C1=C(SC2=C1SC3=C2SC4=C3SC(=C4)C(=O)O)C(=O)O Chemical compound C1=C(SC2=C1SC3=C2SC4=C3SC(=C4)C(=O)O)C(=O)O CPZZNABEJQWLJM-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 125000002619 bicyclic group Chemical group 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 125000006413 ring segment Chemical group 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 125000000547 substituted alkyl group Chemical group 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 2
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 2
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 2
- 229940112669 cuprous oxide Drugs 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- PVBRSNZAOAJRKO-UHFFFAOYSA-N ethyl 2-sulfanylacetate Chemical compound CCOC(=O)CS PVBRSNZAOAJRKO-UHFFFAOYSA-N 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 229940050176 methyl chloride Drugs 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 230000037361 pathway Effects 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- JKRCFFQHGMPORJ-UHFFFAOYSA-N 1-chloro-1h-indene Chemical compound C1=CC=C2C(Cl)C=CC2=C1 JKRCFFQHGMPORJ-UHFFFAOYSA-N 0.000 description 1
- ZTEHOZMYMCEYRM-UHFFFAOYSA-N 1-chlorodecane Chemical compound CCCCCCCCCCCl ZTEHOZMYMCEYRM-UHFFFAOYSA-N 0.000 description 1
- VUQPJRPDRDVQMN-UHFFFAOYSA-N 1-chlorooctadecane Chemical compound CCCCCCCCCCCCCCCCCCCl VUQPJRPDRDVQMN-UHFFFAOYSA-N 0.000 description 1
- OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical compound C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000003810 Jones reagent Substances 0.000 description 1
- OKLUZMUKXYWEGD-UHFFFAOYSA-N N-bromobutan-1-imine Chemical compound CCCC=NBr OKLUZMUKXYWEGD-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 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
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 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
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000001723 carbon free-radicals Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 239000000306 component Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229920001577 copolymer Polymers 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
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- LBVWYGNGGJURHQ-UHFFFAOYSA-N dicarbon Chemical group [C-]#[C+] LBVWYGNGGJURHQ-UHFFFAOYSA-N 0.000 description 1
- 125000004639 dihydroindenyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 238000010573 double replacement reaction Methods 0.000 description 1
- 238000005516 engineering process 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
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 150000004820 halides Chemical class 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
- 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
- 239000005457 ice water Substances 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 125000005645 linoleyl group Chemical group 0.000 description 1
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- 229920002521 macromolecule Polymers 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 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
- 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
- 230000005693 optoelectronics Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
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- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 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 1
- UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-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
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 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
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 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
- 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
- MFRADFLAMWVOTG-UHFFFAOYSA-N thieno[3,2-b]thiophene-3,5-dicarboxylic acid Chemical compound S1C2=C(C=C1C(=O)O)SC=C2C(=O)O MFRADFLAMWVOTG-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 125000001425 triazolyl group Chemical group 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/782,055 US8217183B2 (en) | 2010-05-18 | 2010-05-18 | Methods of making fused thiophenes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201219402A TW201219402A (en) | 2012-05-16 |
| TWI510493B true TWI510493B (zh) | 2015-12-01 |
Family
ID=44358164
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW100116584A TWI510493B (zh) | 2010-05-18 | 2011-05-12 | 製造稠合噻吩之方法 |
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 |
|---|---|---|---|---|
| EP2470584A4 (en) * | 2009-08-28 | 2014-01-22 | Agency Science Tech & Res | POLYMAL SEMICONDUCTORS AND DEVICES THEREFOR AND METHOD THEREFOR |
| 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 |
| EP3147287A1 (en) | 2014-02-28 | 2017-03-29 | Corning Incorporated | Diketopyrrolopyrrole semiconducting materials, processes for their preparation and uses thereof |
| EP3208273B1 (en) * | 2014-11-25 | 2019-07-10 | Fujifilm Corporation | Organic semiconductor element and production method for same, organic semiconductor composition, organic semiconductor film, compound, and oligomer or polymer |
| 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 |
| CN109715696B (zh) | 2016-09-16 | 2022-03-04 | 康宁股份有限公司 | 稠合噻吩-芳基噻二唑聚合物、制造所述聚合物的方法及其用途 |
| 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 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006031893A2 (en) * | 2004-09-14 | 2006-03-23 | Corning Incorporated | Fused thiophenes, methods for making fused thiophenes, and uses thereof |
| CN101429189A (zh) * | 2008-12-24 | 2009-05-13 | 沈阳药科大学 | 2,3-二取代芳基噻吩类衍生物及其用途 |
Family Cites Families (9)
| 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 |
| ES2531660T3 (es) | 2003-08-01 | 2015-03-18 | Mitsubishi Tanabe Pharma Corporation | Compuestos novedosos que tienen actividad inhibidora frente a transportador de glucosa dependiente de sodio |
| US7838623B2 (en) | 2004-09-14 | 2010-11-23 | Corning Incorporated | Fused thiophenes, methods for making fused thiophenes, and uses thereof |
| 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 |
| KR101503681B1 (ko) * | 2006-01-19 | 2015-03-19 | 아더시스 인코포레이티드 | 세로토닌 5-ｈｔ2ｃ 수용체 리간드로서의 티오페닐 및 피롤릴 아제핀 및 이의 용도 |
| 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 |
| 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 JP JP2013511225A patent/JP5778257B2/ja not_active Expired - Fee Related
- 2011-05-12 WO PCT/US2011/036180 patent/WO2011146308A1/en not_active Ceased
- 2011-05-12 EP EP11731558.0A patent/EP2571888B1/en not_active Not-in-force
- 2011-05-12 CN CN201180024452.8A patent/CN103025742B/zh active Active
- 2011-05-12 TW TW100116584A patent/TWI510493B/zh not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006031893A2 (en) * | 2004-09-14 | 2006-03-23 | Corning Incorporated | Fused thiophenes, methods for making fused thiophenes, and uses thereof |
| CN101429189A (zh) * | 2008-12-24 | 2009-05-13 | 沈阳药科大学 | 2,3-二取代芳基噻吩类衍生物及其用途 |
Non-Patent Citations (2)
| Title |
|---|
| Mingqian He et al., Synthesis and Structure of Alkyl-Substituted Fused Thiophenes Containing up to Seven Rings, J. Org. Chem., vol.72, 2007, pp.442-451 * |
| Mohamed Abarbri et al., Preparation of New Polyfunctional Magnesiated Heterocycles Using a Chlorine-, Bromine-, or Iodine-Magnesium Exchange, J. Org. Chem., vol.65, 2000, pp.4618-4634 * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2011146308A1 (en) | 2011-11-24 |
| EP2571888A1 (en) | 2013-03-27 |
| CN103025742A (zh) | 2013-04-03 |
| EP2571888B1 (en) | 2014-12-31 |
| US8217183B2 (en) | 2012-07-10 |
| US20110288306A1 (en) | 2011-11-24 |
| TW201219402A (en) | 2012-05-16 |
| JP5778257B2 (ja) | 2015-09-16 |
| CN103025742B (zh) | 2015-09-09 |
| JP2013533216A (ja) | 2013-08-22 |
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| MM4A | Annulment or lapse of patent due to non-payment of fees |