CA1202141A - Polymeres electroactifs - Google Patents

Polymeres electroactifs

Info

Publication number: CA1202141A
Authority: CA; Canada
Prior art keywords: electroactive polymer; polymer according; diradicals; carbon atoms; polymer
Prior art date: 1981-05-18
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000403132A

Other languages

English (en)

Inventor

Yoram S. Papir

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Chevron USA Inc

Original Assignee

Chevron Research and Technology Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1981-05-18

Filing date

1982-05-17

Publication date

1986-03-18

1982-04-22 Priority claimed from US06/370,231 external-priority patent/US4519937A/en

1982-05-17 Application filed by Chevron Research and Technology Co filed Critical Chevron Research and Technology Co

1986-03-18 Application granted granted Critical

1986-03-18 Publication of CA1202141A publication Critical patent/CA1202141A/fr

Status Expired legal-status Critical Current

Links

229920001746 electroactive polymer Polymers 0.000 title claims abstract description 86
229920000642 polymer Polymers 0.000 claims abstract description 200
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 32
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 20
239000002019 doping agent Substances 0.000 claims description 78
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 62
239000000203 mixture Substances 0.000 claims description 43
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 42
125000004432 carbon atom Chemical group C* 0.000 claims description 38
-1 hydroxy, carboxy Chemical group 0.000 claims description 37
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 33
229910052757 nitrogen Inorganic materials 0.000 claims description 22
FSEXLNMNADBYJU-UHFFFAOYSA-N alpha-Phenylquinoline Natural products C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 claims description 21
150000001768 cations Chemical group 0.000 claims description 18
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 14
125000003118 aryl group Chemical group 0.000 claims description 14
150000002500 ions Chemical class 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
230000002441 reversible effect Effects 0.000 claims description 12
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 11
150000003248 quinolines Chemical class 0.000 claims description 11
125000003342 alkenyl group Chemical group 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 9
XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 9
125000004122 cyclic group Chemical group 0.000 claims description 9
125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
125000001424 substituent group Chemical group 0.000 claims description 9
125000004429 atom Chemical group 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 7
125000004414 alkyl thio group Chemical group 0.000 claims description 6
150000002537 isoquinolines Chemical class 0.000 claims description 6
238000007254 oxidation reaction Methods 0.000 claims description 6
230000009467 reduction Effects 0.000 claims description 6
239000004305 biphenyl Substances 0.000 claims description 5
235000010290 biphenyl Nutrition 0.000 claims description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
SMWDFEZZVXVKRB-UHFFFAOYSA-O hydron;quinoline Chemical compound [NH+]1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-O 0.000 claims description 5
230000003647 oxidation Effects 0.000 claims description 5
QWNCDHYYJATYOG-UHFFFAOYSA-N 2-phenylquinoxaline Chemical compound C1=CC=CC=C1C1=CN=C(C=CC=C2)C2=N1 QWNCDHYYJATYOG-UHFFFAOYSA-N 0.000 claims description 4
229910001413 alkali metal ion Inorganic materials 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
125000004663 dialkyl amino group Chemical group 0.000 claims description 4
230000004927 fusion Effects 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
229910021645 metal ion Inorganic materials 0.000 claims description 4
125000000304 alkynyl group Chemical group 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
GDAXJBDYNVDMDF-UHFFFAOYSA-N 1,2,4-benzotriazine Chemical compound N1=NC=NC2=CC=CC=C21 GDAXJBDYNVDMDF-UHFFFAOYSA-N 0.000 claims description 2
VMLKTERJLVWEJJ-UHFFFAOYSA-N 1,5-naphthyridine Chemical compound C1=CC=NC2=CC=CN=C21 VMLKTERJLVWEJJ-UHFFFAOYSA-N 0.000 claims description 2
VSOSXKMEQPYESP-UHFFFAOYSA-N 1,6-naphthyridine Chemical compound C1=CN=CC2=CC=CN=C21 VSOSXKMEQPYESP-UHFFFAOYSA-N 0.000 claims description 2
MXBVNILGVJVVMH-UHFFFAOYSA-N 1,7-naphthyridine Chemical compound C1=NC=CC2=CC=CN=C21 MXBVNILGVJVVMH-UHFFFAOYSA-N 0.000 claims description 2
HCMMECMKVPHMDE-UHFFFAOYSA-N 2,7-naphthyridine Chemical compound C1=NC=C2C=NC=CC2=C1 HCMMECMKVPHMDE-UHFFFAOYSA-N 0.000 claims description 2
150000001356 alkyl thiols Chemical class 0.000 claims description 2
JTCXNGLQZYVVBF-UHFFFAOYSA-N cinnoline;quinazoline Chemical compound N1=NC=CC2=CC=CC=C21.N1=CN=CC2=CC=CC=C21 JTCXNGLQZYVVBF-UHFFFAOYSA-N 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 claims description 2
CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 claims description 2
XFEVEGNEHPLFGK-UHFFFAOYSA-N pyrazino[2,3-d]pyridazine Chemical compound C1=NN=CC2=NC=CN=C21 XFEVEGNEHPLFGK-UHFFFAOYSA-N 0.000 claims description 2
YEYHFKBVNARCNE-UHFFFAOYSA-N pyrido[2,3-b]pyrazine Chemical compound N1=CC=NC2=CC=CN=C21 YEYHFKBVNARCNE-UHFFFAOYSA-N 0.000 claims description 2
UDJFFSGCRRMVFH-UHFFFAOYSA-N pyrido[2,3-d]pyrimidine Chemical compound N1=CN=CC2=CC=CN=C21 UDJFFSGCRRMVFH-UHFFFAOYSA-N 0.000 claims description 2
BWESROVQGZSBRX-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine Chemical compound C1=NC=NC2=CC=CN=C21 BWESROVQGZSBRX-UHFFFAOYSA-N 0.000 claims description 2
IHYJXEQIZYROGA-UHFFFAOYSA-N pyrido[3,4-d]pyridazine Chemical compound N1=NC=C2C=NC=CC2=C1 IHYJXEQIZYROGA-UHFFFAOYSA-N 0.000 claims description 2
PAQYIEZTLSDLQO-UHFFFAOYSA-N pyrido[3,4-d]pyrimidine Chemical compound N1=CN=C2C=NC=CC2=C1 PAQYIEZTLSDLQO-UHFFFAOYSA-N 0.000 claims description 2
PLZDHJUUEGCXJH-UHFFFAOYSA-N pyrido[4,3-d]pyrimidine Chemical compound C1=NC=C2C=NC=CC2=N1 PLZDHJUUEGCXJH-UHFFFAOYSA-N 0.000 claims description 2
QGDYVSSVBYMOJN-UHFFFAOYSA-N pyrimido[4,5-d]pyrimidine Chemical compound C1=NC=NC2=NC=NC=C21 QGDYVSSVBYMOJN-UHFFFAOYSA-N 0.000 claims description 2
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
229910052784 alkaline earth metal Inorganic materials 0.000 claims 3
JBFWVXIWQBWEKM-UHFFFAOYSA-N pyridazino[4,5-d]pyridazine Chemical compound N1=NC=C2C=NN=CC2=C1 JBFWVXIWQBWEKM-UHFFFAOYSA-N 0.000 claims 2
BAPDWOBBGGGGOC-UHFFFAOYSA-N 1,8-naphthyridine;2,6-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21.N1=CC=C2C=NC=CC2=C1 BAPDWOBBGGGGOC-UHFFFAOYSA-N 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
FQOBINBWTPHVEO-UHFFFAOYSA-N pyrazino[2,3-b]pyrazine Chemical compound N1=CC=NC2=NC=CN=C21 FQOBINBWTPHVEO-UHFFFAOYSA-N 0.000 claims 1
OUFHXMSGJIYFPW-UHFFFAOYSA-N pyrazino[2,3-c]pyridazine Chemical compound N1=NC=CC2=NC=CN=C21 OUFHXMSGJIYFPW-UHFFFAOYSA-N 0.000 claims 1
GIVUQTUKKWDKHE-UHFFFAOYSA-N pyrido[2,3-d]pyridazine Chemical compound C1=NN=CC2=CC=CN=C21 GIVUQTUKKWDKHE-UHFFFAOYSA-N 0.000 claims 1
GHKGSHZMWWDYKI-UHFFFAOYSA-N pyrido[2,3-e][1,2,4]triazine Chemical compound N1=CN=NC2=CC=CN=C21 GHKGSHZMWWDYKI-UHFFFAOYSA-N 0.000 claims 1
UVGCYMVPDRDDDT-UHFFFAOYSA-N pyrimido[4,5-c]pyridazine Chemical compound N1=CN=C2N=NC=CC2=C1 UVGCYMVPDRDDDT-UHFFFAOYSA-N 0.000 claims 1
KXNFMBIDXYJDEP-UHFFFAOYSA-N pyrimido[4,5-d]pyridazine Chemical compound C1=NN=CC2=NC=NC=C21 KXNFMBIDXYJDEP-UHFFFAOYSA-N 0.000 claims 1
MOLVBKBUIUHRRR-UHFFFAOYSA-N pyrimido[4,5-e][1,2,4]triazine Chemical compound N1=NC=NC2=NC=NC=C21 MOLVBKBUIUHRRR-UHFFFAOYSA-N 0.000 claims 1
JOZPEVMCAKXSEY-UHFFFAOYSA-N pyrimido[5,4-d]pyrimidine Chemical compound N1=CN=CC2=NC=NC=C21 JOZPEVMCAKXSEY-UHFFFAOYSA-N 0.000 claims 1
150000003252 quinoxalines Chemical class 0.000 claims 1
239000003607 modifier Substances 0.000 abstract description 14
239000000243 solution Substances 0.000 description 62
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 55
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
239000010408 film Substances 0.000 description 35
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 31
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 30
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
238000000034 method Methods 0.000 description 25
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
239000000047 product Substances 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 18
235000019441 ethanol Nutrition 0.000 description 18
239000000463 material Substances 0.000 description 18
238000002360 preparation method Methods 0.000 description 18
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
229960005419 nitrogen Drugs 0.000 description 14
229940086542 triethylamine Drugs 0.000 description 14
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
150000001875 compounds Chemical class 0.000 description 12
229920001577 copolymer Polymers 0.000 description 11
238000007598 dipping method Methods 0.000 description 11
229940021013 electrolyte solution Drugs 0.000 description 10
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
239000008151 electrolyte solution Substances 0.000 description 9
230000000694 effects Effects 0.000 description 8
238000005259 measurement Methods 0.000 description 8
229940073584 methylene chloride Drugs 0.000 description 8
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
238000010992 reflux Methods 0.000 description 8
239000007787 solid Substances 0.000 description 8
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 8
150000001450 anions Chemical class 0.000 description 7
229920000620 organic polymer Polymers 0.000 description 7
PRSWVGYKUDIOEU-UHFFFAOYSA-N sodium;1h-anthracen-1-ide Chemical compound [Na+].[C-]1=CC=CC2=CC3=CC=CC=C3C=C21 PRSWVGYKUDIOEU-UHFFFAOYSA-N 0.000 description 7
QLUMLEDLZDMGDW-UHFFFAOYSA-N sodium;1h-naphthalen-1-ide Chemical compound [Na+].[C-]1=CC=CC2=CC=CC=C21 QLUMLEDLZDMGDW-UHFFFAOYSA-N 0.000 description 7
229920000292 Polyquinoline Polymers 0.000 description 6
239000012298 atmosphere Substances 0.000 description 6
238000010348 incorporation Methods 0.000 description 6
239000002904 solvent Substances 0.000 description 6
239000000126 substance Substances 0.000 description 6
239000010409 thin film Substances 0.000 description 6
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
239000004020 conductor Substances 0.000 description 5
238000001035 drying Methods 0.000 description 5
238000012986 modification Methods 0.000 description 5
230000004048 modification Effects 0.000 description 5
230000008569 process Effects 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
239000012212 insulator Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
229920002521 macromolecule Polymers 0.000 description 4
230000001590 oxidative effect Effects 0.000 description 4
SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 4
238000006116 polymerization reaction Methods 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
238000006722 reduction reaction Methods 0.000 description 4
239000007858 starting material Substances 0.000 description 4
CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Inorganic materials [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 3
239000003513 alkali Substances 0.000 description 3
125000000129 anionic group Chemical group 0.000 description 3
229910052786 argon Inorganic materials 0.000 description 3
238000005345 coagulation Methods 0.000 description 3
230000015271 coagulation Effects 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
239000011521 glass Substances 0.000 description 3
229920001519 homopolymer Polymers 0.000 description 3
229910001496 lithium tetrafluoroborate Inorganic materials 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
229920000447 polyanionic polymer Polymers 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
238000011160 research Methods 0.000 description 3
239000011734 sodium Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
SKBBQSLSGRSQAJ-UHFFFAOYSA-N 1-(4-acetylphenyl)ethanone Chemical compound CC(=O)C1=CC=C(C(C)=O)C=C1 SKBBQSLSGRSQAJ-UHFFFAOYSA-N 0.000 description 2
QPHDTFZGPWWPIU-UHFFFAOYSA-N 1-(4-amino-3-benzoylphenyl)ethanone Chemical compound CC(=O)C1=CC=C(N)C(C(=O)C=2C=CC=CC=2)=C1 QPHDTFZGPWWPIU-UHFFFAOYSA-N 0.000 description 2
HHXVQNVADPECCD-UHFFFAOYSA-N 2-methyl-2-(4-nitrophenyl)-1,3-dioxolane Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C1(C)OCCO1 HHXVQNVADPECCD-UHFFFAOYSA-N 0.000 description 2
MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 2
YQYGPGKTNQNXMH-UHFFFAOYSA-N 4-nitroacetophenone Chemical compound CC(=O)C1=CC=C([N+]([O-])=O)C=C1 YQYGPGKTNQNXMH-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
241001663154 Electron Species 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
IDVPXBIYMFWUEF-UHFFFAOYSA-N [2-amino-5-(2-methyl-1,3-dioxolan-2-yl)phenyl]-phenylmethanone Chemical compound C=1C=C(N)C(C(=O)C=2C=CC=CC=2)=CC=1C1(C)OCCO1 IDVPXBIYMFWUEF-UHFFFAOYSA-N 0.000 description 2
150000001351 alkyl iodides Chemical class 0.000 description 2
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
125000002091 cationic group Chemical group 0.000 description 2
230000008859 change Effects 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
125000005594 diketone group Chemical group 0.000 description 2
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
229960001760 dimethyl sulfoxide Drugs 0.000 description 2
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
239000000835 fiber Substances 0.000 description 2
239000007789 gas Substances 0.000 description 2
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
229910052737 gold Inorganic materials 0.000 description 2
239000010931 gold Substances 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
230000002427 irreversible effect Effects 0.000 description 2
239000006193 liquid solution Substances 0.000 description 2
239000002932 luster Substances 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
UKOVZLWSUZKTRL-UHFFFAOYSA-N naphthalid Chemical compound C1=CC(C(=O)OC2)=C3C2=CC=CC3=C1 UKOVZLWSUZKTRL-UHFFFAOYSA-N 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
150000004767 nitrides Chemical class 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
229910052697 platinum Inorganic materials 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000010791 quenching Methods 0.000 description 2
230000000171 quenching effect Effects 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
238000003892 spreading Methods 0.000 description 2
230000007480 spreading Effects 0.000 description 2
239000013589 supplement Substances 0.000 description 2
239000003115 supporting electrolyte Substances 0.000 description 2
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 1
125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 1
UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 1
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NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-N 0.000 description 1
PACGLQCRGWFBJH-UHFFFAOYSA-N 2-(4-methoxyphenyl)acetonitrile Chemical compound COC1=CC=C(CC#N)C=C1 PACGLQCRGWFBJH-UHFFFAOYSA-N 0.000 description 1
IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 description 1
QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
XDKVHSLZGHWGND-UHFFFAOYSA-N 2h-pyrido[1,2-a]pyrazine Chemical compound C1=CC=CC2=CNC=CN21 XDKVHSLZGHWGND-UHFFFAOYSA-N 0.000 description 1
NDXGRHCEHPFUSU-UHFFFAOYSA-N 3-(3-aminophenyl)aniline Chemical group NC1=CC=CC(C=2C=C(N)C=CC=2)=C1 NDXGRHCEHPFUSU-UHFFFAOYSA-N 0.000 description 1
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
HTNPXVDBSMVQMI-UHFFFAOYSA-N 3-phenyl-2,1-benzoxazole Chemical compound C1=CC=CC=C1C1=C2C=CC=CC2=NO1 HTNPXVDBSMVQMI-UHFFFAOYSA-N 0.000 description 1
DYFKQCASEWRXIN-UHFFFAOYSA-N 3-phenyl-5-[(3-phenyl-2,1-benzoxazol-5-yl)oxy]-2,1-benzoxazole Chemical compound C1=CC2=NOC(C=3C=CC=CC=3)=C2C=C1OC(=CC1=2)C=CC1=NOC=2C1=CC=CC=C1 DYFKQCASEWRXIN-UHFFFAOYSA-N 0.000 description 1
125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
KOGDFDWINXIWHI-UHFFFAOYSA-N 4-[2-(4-aminophenyl)ethenyl]aniline Chemical group C1=CC(N)=CC=C1C=CC1=CC=C(N)C=C1 KOGDFDWINXIWHI-UHFFFAOYSA-N 0.000 description 1
UHNUHZHQLCGZDA-UHFFFAOYSA-N 4-[2-(4-aminophenyl)ethyl]aniline Chemical compound C1=CC(N)=CC=C1CCC1=CC=C(N)C=C1 UHNUHZHQLCGZDA-UHFFFAOYSA-N 0.000 description 1
IVYMIRMKXZAHRV-UHFFFAOYSA-N 4-chlorophenylacetonitrile Chemical compound ClC1=CC=C(CC#N)C=C1 IVYMIRMKXZAHRV-UHFFFAOYSA-N 0.000 description 1
125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
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UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 1
BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
LOCUXGFHUYBUHF-UHFFFAOYSA-N 4-phenylquinoline Chemical compound C1=CC=CC=C1C1=CC=NC2=CC=CC=C12 LOCUXGFHUYBUHF-UHFFFAOYSA-N 0.000 description 1
SDTHIDMOBRXVOQ-UHFFFAOYSA-N 5-[bis(2-chloroethyl)amino]-6-methyl-1h-pyrimidine-2,4-dione Chemical compound CC=1NC(=O)NC(=O)C=1N(CCCl)CCCl SDTHIDMOBRXVOQ-UHFFFAOYSA-N 0.000 description 1
229910017048 AsF6 Inorganic materials 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
SYAVNVUADGYYDF-UHFFFAOYSA-N C1(=CC=CC=C1)CC#N.CC1(OCCO1)C=1C=CC=2C(=C(ON2)C2=CC=CC=C2)C1 Chemical compound C1(=CC=CC=C1)CC#N.CC1(OCCO1)C=1C=CC=2C(=C(ON2)C2=CC=CC=C2)C1 SYAVNVUADGYYDF-UHFFFAOYSA-N 0.000 description 1
YOSDSOCGHBXQRZ-UHFFFAOYSA-N C1(=CC=CC=C1)CC#N.O(C=1C=CC=2C(=C(ON2)C2=CC=CC=C2)C1)C=1C=CC=2C(=C(ON2)C2=CC=CC=C2)C1 Chemical compound C1(=CC=CC=C1)CC#N.O(C=1C=CC=2C(=C(ON2)C2=CC=CC=C2)C1)C=1C=CC=2C(=C(ON2)C2=CC=CC=C2)C1 YOSDSOCGHBXQRZ-UHFFFAOYSA-N 0.000 description 1
101100379067 Caenorhabditis elegans anc-1 gene Proteins 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
102100024133 Coiled-coil domain-containing protein 50 Human genes 0.000 description 1
QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
229910015400 FeC13 Inorganic materials 0.000 description 1
101000910772 Homo sapiens Coiled-coil domain-containing protein 50 Proteins 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
101100010166 Mus musculus Dok3 gene Proteins 0.000 description 1
PUBAPHOVKLXWGT-UHFFFAOYSA-N NC1=C(C=C(C=C1)C1=CC(=C(C=C1)N)C(C1=CC=CC=C1)=O)C(C1=CC=CC=C1)=O.C(C)(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)C(C)=O Chemical group NC1=C(C=C(C=C1)C1=CC(=C(C=C1)N)C(C1=CC=CC=C1)=O)C(C1=CC=CC=C1)=O.C(C)(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)C(C)=O PUBAPHOVKLXWGT-UHFFFAOYSA-N 0.000 description 1
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
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CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
229910052770 Uranium Inorganic materials 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
XDHPHFIZKMWVAQ-UHFFFAOYSA-N [2-amino-5-(4-amino-3-benzoylphenyl)phenyl]-phenylmethanone Chemical group NC1=CC=C(C=2C=C(C(N)=CC=2)C(=O)C=2C=CC=CC=2)C=C1C(=O)C1=CC=CC=C1 XDHPHFIZKMWVAQ-UHFFFAOYSA-N 0.000 description 1
VGBQXJMJGZUBMA-UHFFFAOYSA-N [2-amino-5-(4-amino-3-benzoylphenyl)phenyl]-phenylmethanone (2-amino-4-bromophenyl)-phenylmethanone Chemical compound BrC1=CC(=C(C(=O)C2=CC=CC=C2)C=C1)N.NC1=C(C=C(C=C1)C1=CC(=C(C=C1)N)C(C1=CC=CC=C1)=O)C(C1=CC=CC=C1)=O VGBQXJMJGZUBMA-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000012300 argon atmosphere Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
239000002585 base Substances 0.000 description 1
HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
230000015572 biosynthetic process Effects 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
238000001311 chemical methods and process Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
229920001940 conductive polymer Polymers 0.000 description 1
229930003836 cresol Natural products 0.000 description 1
239000012043 crude product Substances 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
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000950 dibromo group Chemical group Br* 0.000 description 1
125000003963 dichloro group Chemical group Cl* 0.000 description 1
SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
230000005611 electricity Effects 0.000 description 1
239000003792 electrolyte Substances 0.000 description 1
238000006056 electrooxidation reaction Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
229910052734 helium Inorganic materials 0.000 description 1
239000001307 helium Substances 0.000 description 1
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
RSPZSDWVQWRAEF-UHFFFAOYSA-N hepta-1,6-diyne Chemical compound C#CCCCC#C RSPZSDWVQWRAEF-UHFFFAOYSA-N 0.000 description 1
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
239000011147 inorganic material Substances 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
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000000155 melt Substances 0.000 description 1
ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
239000000178 monomer Substances 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
150000002815 nickel Chemical class 0.000 description 1
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
150000002892 organic cations Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
238000010525 oxidative degradation reaction Methods 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000012071 phase Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
229920000128 polypyrrole Polymers 0.000 description 1
239000011698 potassium fluoride Substances 0.000 description 1
235000003270 potassium fluoride Nutrition 0.000 description 1
230000003334 potential effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
AZOUBRBBWKBGFS-UHFFFAOYSA-N pyrimido[1,2-a]pyrimidin-5-ium Chemical compound N1=CC=C[N+]2=CC=CN=C21 AZOUBRBBWKBGFS-UHFFFAOYSA-N 0.000 description 1
230000036647 reaction Effects 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000011946 reduction process Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000000523 sample Substances 0.000 description 1
229920006395 saturated elastomer Polymers 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
239000004065 semiconductor Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910052979 sodium sulfide Inorganic materials 0.000 description 1
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
230000003068 static effect Effects 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
238000003786 synthesis reaction 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
238000004809 thin layer chromatography Methods 0.000 description 1
125000004417 unsaturated alkyl group Chemical group 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
230000004580 weight loss Effects 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings condensed with carbocyclic rings or ring systems
- 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/16—Radicals substituted by halogen atoms or nitro radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/28—Radicals substituted by nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0683—Polycondensates containing six-membered rings, condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0688—Polycondensates containing six-membered rings, condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only one nitrogen atom in the ring, e.g. polyquinolines
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0683—Polycondensates containing six-membered rings, condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0694—Polycondensates containing six-membered rings, condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only two nitrogen atoms in the ring, e.g. polyquinoxalines
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
- H01B1/124—Intrinsically conductive polymers
- H01B1/128—Intrinsically conductive polymers comprising six-membered aromatic rings in the main chain, e.g. polyanilines, polyphenylenes
- 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
- 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
- H10K85/114—Poly-phenylenevinylene; Derivatives thereof
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/30—Doping active layers, e.g. electron transporting layers
- 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

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Materials Engineering (AREA)
Engineering & Computer Science (AREA)
Spectroscopy & Molecular Physics (AREA)
Physics & Mathematics (AREA)
Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Compositions Of Macromolecular Compounds (AREA)

CA000403132A 1981-05-18 1982-05-17 Polymeres electroactifs Expired CA1202141A (fr)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US26491581A	1981-05-18	1981-05-18
US264,915		1981-05-18
US30441081A	1981-09-21	1981-09-21
US304,410		1981-09-21
US370,231		1982-04-22
US06/370,231 US4519937A (en)	1981-09-21	1982-04-22	Electroactive polymers

Publications (1)

Publication Number	Publication Date
CA1202141A true CA1202141A (fr)	1986-03-18

Family

ID=27401744

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000403132A Expired CA1202141A (fr)	1981-05-18	1982-05-17	Polymeres electroactifs

Country Status (8)

Country	Link
KR (1)	KR830010134A (fr)
CA (1)	CA1202141A (fr)
DE (1)	DE3218762A1 (fr)
FR (1)	FR2505854B1 (fr)
GB (2)	GB2143245B (fr)
IL (1)	IL65709A (fr)
IT (1)	IT1203690B (fr)
NL (1)	NL8202016A (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0126064A4 (fr) *	1982-11-17	1985-07-01	Chevron Res	Polymeres electroactifs.
US4537843A (en) *	1983-10-26	1985-08-27	Showa Denko Kabushiki Kaisha	Secondary battery
US4613211A (en) *	1983-11-21	1986-09-23	Chevron Research Company	Electrochromic devices
US4966954A (en) *	1987-03-04	1990-10-30	Rensselaer Polytechnic Institute	Production and processing of thermally stable polyenaminonitriles and polyaminoquinolines therefrom
US5053478A (en) *	1987-03-04	1991-10-01	Moore James A	Production and processing of thermally stable polyenaminonitriles
DE4024120A1 (de) *	1990-07-30	1992-02-06	Basf Ag	Amionbenzophenonsulfonsaeuren
TW349948B (en) *	1995-10-31	1999-01-11	Janssen Pharmaceutica Nv	Farnesyl transferase inhibiting 2-quinolone derivatives

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4222903A (en) *	1978-05-04	1980-09-16	University Patents, Inc.	P-Type electrically conducting doped polyacetylene film and method of preparing same
US4230604A (en) *	1978-10-30	1980-10-28	Conoco, Inc.	Polymeric electrical conductance dependent upon electrical potential

1982
- 1982-05-07 IL IL65709A patent/IL65709A/xx not_active IP Right Cessation
- 1982-05-14 NL NL8202016A patent/NL8202016A/nl not_active Application Discontinuation
- 1982-05-17 FR FR8208557A patent/FR2505854B1/fr not_active Expired
- 1982-05-17 GB GB08420659A patent/GB2143245B/en not_active Expired
- 1982-05-17 GB GB08214342A patent/GB2103227B/en not_active Expired
- 1982-05-17 IT IT21304/82A patent/IT1203690B/it active
- 1982-05-17 KR KR1019820002136A patent/KR830010134A/ko not_active Ceased
- 1982-05-17 CA CA000403132A patent/CA1202141A/fr not_active Expired
- 1982-05-18 DE DE3218762A patent/DE3218762A1/de not_active Ceased

Also Published As

Publication number	Publication date
KR830010134A (ko)	1983-12-26
FR2505854B1 (fr)	1988-07-08
GB2103227A (en)	1983-02-16
GB2103227B (en)	1985-10-16
NL8202016A (nl)	1982-12-16
IT1203690B (it)	1989-02-15
GB8420659D0 (en)	1984-09-19
DE3218762A1 (de)	1983-02-24
IL65709A (en)	1986-01-31
FR2505854A1 (fr)	1982-11-19
IT8221304A0 (it)	1982-05-17
GB2143245B (en)	1985-10-16
GB2143245A (en)	1985-02-06
IL65709A0 (en)	1982-08-31

Legal Events

Date	Code	Title	Description
2003-03-18	MKEX	Expiry

Publication	Publication Date	Title
US4519938A (en)	1985-05-28	Electroactive polymers
US4522745A (en)	1985-06-11	Fused 5,6,5-membered heterocyclic electroactive polymers
US4505840A (en)	1985-03-19	Heterocyclic electroactive polymers
US4505841A (en)	1985-03-19	Fused 6,6,6-membered heterocyclic electroactive polymers
US4579679A (en)	1986-04-01	Electroactive polymers
US4882243A (en)	1989-11-21	Preparation of metallic cation conducting polymers based on sterically hindered phenols containing polymeric systems
US4505844A (en)	1985-03-19	P-Type polyphenoxazine electroactive polymers
US4505843A (en)	1985-03-19	Heterodiazole electroactive polymers
CA1202141A (fr)	1986-03-18	Polymeres electroactifs
US4519937A (en)	1985-05-28	Electroactive polymers
US7273918B2 (en)	2007-09-25	Thermally stable self-doped functionalized polyanilines
EP0180412B1 (fr)	1992-01-02	Polymères de bicarbazol-oxadiazol électroactifs
US4502980A (en)	1985-03-05	Dithiene electroactive polymers
US4519940A (en)	1985-05-28	Triazole electroactive polymers
US5578699A (en)	1996-11-26	Process for making amino functional poly(para-phenylene vinylene)s
US4505842A (en)	1985-03-19	Heteroazole electroactive polymers
JPS63215722A (ja)	1988-09-08	電導性ポリアニリン系化合物の製造方法
CA1202142A (fr)	1986-03-18	Polymeres electroactifs
US4597896A (en)	1986-07-01	Carbazole-oxadiazole electroactive polymers
JPS5927950A (ja)	1984-02-14	電気活性複素環式ポリマ−
JPH07254307A (ja)	1995-10-03	導電性重合体組成物
JPH05117526A (ja)	1993-05-14	導電性組成物の製造方法