CA2377671C - High density non-volatile memory device - Google Patents
High density non-volatile memory device Download PDFInfo
- Publication number
- CA2377671C CA2377671C CA2377671A CA2377671A CA2377671C CA 2377671 C CA2377671 C CA 2377671C CA 2377671 A CA2377671 A CA 2377671A CA 2377671 A CA2377671 A CA 2377671A CA 2377671 C CA2377671 C CA 2377671C
- Authority
- CA
- Canada
- Prior art keywords
- molecular memory
- storage medium
- molecule
- group
- porphyrin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 238000003860 storage Methods 0.000 claims abstract description 421
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 308
- 230000003647 oxidation Effects 0.000 claims abstract description 305
- 230000015654 memory Effects 0.000 claims abstract description 158
- 150000004032 porphyrins Chemical class 0.000 claims description 458
- -1 cyclic polyene Chemical class 0.000 claims description 180
- 238000000034 method Methods 0.000 claims description 124
- 229910052737 gold Inorganic materials 0.000 claims description 98
- 125000005647 linker group Chemical group 0.000 claims description 96
- 125000001424 substituent group Chemical group 0.000 claims description 76
- 229910052751 metal Inorganic materials 0.000 claims description 62
- 239000002184 metal Substances 0.000 claims description 62
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 claims description 60
- 239000000758 substrate Substances 0.000 claims description 59
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 46
- 125000003118 aryl group Chemical group 0.000 claims description 39
- 150000002678 macrocyclic compounds Chemical class 0.000 claims description 38
- 229910052725 zinc Inorganic materials 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- 229910052749 magnesium Inorganic materials 0.000 claims description 26
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 22
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 22
- 125000002252 acyl group Chemical group 0.000 claims description 21
- 125000003368 amide group Chemical group 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical group 0.000 claims description 21
- 125000004076 pyridyl group Chemical group 0.000 claims description 21
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 21
- 125000004962 sulfoxyl group Chemical group 0.000 claims description 21
- 229910052717 sulfur Inorganic materials 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000003282 alkyl amino group Chemical group 0.000 claims description 20
- 125000004414 alkyl thio group Chemical group 0.000 claims description 20
- 150000002739 metals Chemical class 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 16
- 229910052711 selenium Inorganic materials 0.000 claims description 14
- 229910052714 tellurium Inorganic materials 0.000 claims description 14
- 238000004832 voltammetry Methods 0.000 claims description 13
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 12
- 229910052709 silver Inorganic materials 0.000 claims description 12
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 10
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 10
- 229910052748 manganese Inorganic materials 0.000 claims description 10
- 229910052759 nickel Inorganic materials 0.000 claims description 10
- 229910052697 platinum Inorganic materials 0.000 claims description 10
- 150000004291 polyenes Chemical class 0.000 claims description 10
- 229920000642 polymer Polymers 0.000 claims description 10
- 229910052782 aluminium Inorganic materials 0.000 claims description 9
- 229910052796 boron Inorganic materials 0.000 claims description 9
- 229910052793 cadmium Inorganic materials 0.000 claims description 9
- 239000003989 dielectric material Substances 0.000 claims description 9
- 229910052733 gallium Inorganic materials 0.000 claims description 9
- 229910052741 iridium Inorganic materials 0.000 claims description 9
- 229910052745 lead Inorganic materials 0.000 claims description 9
- 229910052763 palladium Inorganic materials 0.000 claims description 9
- 229910052703 rhodium Inorganic materials 0.000 claims description 9
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 8
- 229910052718 tin Inorganic materials 0.000 claims description 8
- 238000012545 processing Methods 0.000 claims description 6
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 5
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 5
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 claims description 5
- MWVTWFVJZLCBMC-UHFFFAOYSA-N 4,4'-bipyridine Chemical group C1=NC=CC(C=2C=CN=CC=2)=C1 MWVTWFVJZLCBMC-UHFFFAOYSA-N 0.000 claims description 5
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 claims description 5
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 5
- 101710158075 Bucky ball Proteins 0.000 claims description 5
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 claims description 5
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 5
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 claims description 5
- 150000004696 coordination complex Chemical class 0.000 claims description 5
- NLUNLVTVUDIHFE-UHFFFAOYSA-N cyclooctylcyclooctane Chemical compound C1CCCCCCC1C1CCCCCCC1 NLUNLVTVUDIHFE-UHFFFAOYSA-N 0.000 claims description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 5
- 230000005684 electric field Effects 0.000 claims description 5
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 claims description 5
- 229950000688 phenothiazine Drugs 0.000 claims description 5
- FHCPAXDKURNIOZ-UHFFFAOYSA-N tetrathiafulvalene Chemical compound S1C=CSC1=C1SC=CS1 FHCPAXDKURNIOZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000005259 triarylamine group Chemical group 0.000 claims description 5
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 4
- UFPVYWYEZPMUQL-UHFFFAOYSA-N 2-(1,3-diselenol-2-ylidene)-1,3-diselenole Chemical compound [Se]1C=C[Se]C1=C1[Se]C=C[Se]1 UFPVYWYEZPMUQL-UHFFFAOYSA-N 0.000 claims description 4
- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 claims description 4
- LLCSWKVOHICRDD-UHFFFAOYSA-N buta-1,3-diyne Chemical compound C#CC#C LLCSWKVOHICRDD-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- 238000001566 impedance spectroscopy Methods 0.000 claims description 3
- LGAILEFNHXWAJP-BMEPFDOTSA-N macrocycle Chemical group N([C@H]1[C@@H](C)CC)C(=O)C(N=2)=CSC=2CNC(=O)C(=C(O2)C)N=C2[C@H]([C@@H](C)CC)NC(=O)C2=CSC1=N2 LGAILEFNHXWAJP-BMEPFDOTSA-N 0.000 claims description 3
- 230000010355 oscillation Effects 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 230000015572 biosynthetic process Effects 0.000 abstract description 128
- 238000003786 synthesis reaction Methods 0.000 abstract description 122
- 238000004519 manufacturing process Methods 0.000 abstract description 15
- 230000001066 destructive effect Effects 0.000 abstract description 7
- 230000007547 defect Effects 0.000 abstract description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 255
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 189
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 166
- 239000000203 mixture Substances 0.000 description 136
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 132
- 239000011701 zinc Substances 0.000 description 110
- 239000000243 solution Substances 0.000 description 105
- 239000010931 gold Substances 0.000 description 96
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 89
- 239000000377 silicon dioxide Substances 0.000 description 88
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 76
- 150000001299 aldehydes Chemical class 0.000 description 66
- 125000003396 thiol group Chemical group [H]S* 0.000 description 66
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 65
- 239000007787 solid Substances 0.000 description 64
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 62
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 62
- 210000000352 storage cell Anatomy 0.000 description 59
- 238000006243 chemical reaction Methods 0.000 description 58
- 238000005859 coupling reaction Methods 0.000 description 54
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 53
- 239000000539 dimer Substances 0.000 description 50
- 230000007935 neutral effect Effects 0.000 description 50
- 238000010168 coupling process Methods 0.000 description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
- 229910001868 water Inorganic materials 0.000 description 47
- 238000005481 NMR spectroscopy Methods 0.000 description 46
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 45
- 239000002904 solvent Substances 0.000 description 45
- 238000004440 column chromatography Methods 0.000 description 44
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 42
- 230000002829 reductive effect Effects 0.000 description 42
- 241000894007 species Species 0.000 description 40
- 238000005160 1H NMR spectroscopy Methods 0.000 description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- 230000008878 coupling Effects 0.000 description 34
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 239000013545 self-assembled monolayer Substances 0.000 description 33
- 150000001875 compounds Chemical group 0.000 description 32
- 229910052786 argon Inorganic materials 0.000 description 31
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 30
- 238000000746 purification Methods 0.000 description 29
- 238000013459 approach Methods 0.000 description 28
- 239000011777 magnesium Substances 0.000 description 28
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 27
- 239000003921 oil Substances 0.000 description 27
- 235000019198 oils Nutrition 0.000 description 27
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 25
- 238000006263 metalation reaction Methods 0.000 description 25
- 239000002086 nanomaterial Substances 0.000 description 25
- 239000013078 crystal Substances 0.000 description 23
- 239000012074 organic phase Substances 0.000 description 23
- 238000003491 array Methods 0.000 description 22
- 210000004027 cell Anatomy 0.000 description 22
- 230000005284 excitation Effects 0.000 description 22
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 21
- 238000011065 in-situ storage Methods 0.000 description 21
- 235000017557 sodium bicarbonate Nutrition 0.000 description 21
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 21
- 239000013638 trimer Substances 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
- PBTPREHATAFBEN-UHFFFAOYSA-N dipyrromethane Chemical compound C=1C=CNC=1CC1=CC=CN1 PBTPREHATAFBEN-UHFFFAOYSA-N 0.000 description 20
- 239000000975 dye Substances 0.000 description 20
- 230000008569 process Effects 0.000 description 20
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 19
- 239000010410 layer Substances 0.000 description 19
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 19
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 18
- 238000003776 cleavage reaction Methods 0.000 description 18
- 239000012071 phase Substances 0.000 description 18
- 230000009467 reduction Effects 0.000 description 18
- 238000006722 reduction reaction Methods 0.000 description 18
- PHIUVUGKNBYJJH-UHFFFAOYSA-N s-(4-iodophenyl) ethanethioate Chemical compound CC(=O)SC1=CC=C(I)C=C1 PHIUVUGKNBYJJH-UHFFFAOYSA-N 0.000 description 18
- 230000007017 scission Effects 0.000 description 18
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 17
- 238000009833 condensation Methods 0.000 description 17
- 230000005494 condensation Effects 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- YIYFFLYGSHJWFF-UHFFFAOYSA-N [Zn].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 Chemical class [Zn].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 YIYFFLYGSHJWFF-UHFFFAOYSA-N 0.000 description 15
- 238000004587 chromatography analysis Methods 0.000 description 15
- 230000005055 memory storage Effects 0.000 description 15
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 15
- 239000000178 monomer Substances 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- 238000004809 thin layer chromatography Methods 0.000 description 15
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 14
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 14
- 239000012346 acetyl chloride Substances 0.000 description 14
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 14
- 238000013461 design Methods 0.000 description 14
- 235000019256 formaldehyde Nutrition 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 14
- JYWKEVKEKOTYEX-UHFFFAOYSA-N 2,6-dibromo-4-chloroiminocyclohexa-2,5-dien-1-one Chemical compound ClN=C1C=C(Br)C(=O)C(Br)=C1 JYWKEVKEKOTYEX-UHFFFAOYSA-N 0.000 description 13
- 239000000463 material Substances 0.000 description 13
- 230000003068 static effect Effects 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 12
- 239000000470 constituent Substances 0.000 description 12
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 12
- 230000001404 mediated effect Effects 0.000 description 12
- 230000004044 response Effects 0.000 description 12
- HIKRJHFHGKZKRI-UHFFFAOYSA-N 2,4,6-trimethylbenzaldehyde Chemical compound CC1=CC(C)=C(C=O)C(C)=C1 HIKRJHFHGKZKRI-UHFFFAOYSA-N 0.000 description 11
- 238000012512 characterization method Methods 0.000 description 11
- KNYOXNQCDNALKS-UHFFFAOYSA-N cyclopenta-1,3-diene 4-cyclopenta-2,4-dien-1-ylbenzaldehyde iron(2+) Chemical compound [Fe++].c1cc[cH-]c1.O=Cc1ccc(cc1)-[c-]1cccc1 KNYOXNQCDNALKS-UHFFFAOYSA-N 0.000 description 11
- 238000013500 data storage Methods 0.000 description 11
- 239000002094 self assembled monolayer Substances 0.000 description 11
- 238000004611 spectroscopical analysis Methods 0.000 description 11
- 229910017744 AgPF6 Inorganic materials 0.000 description 10
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 10
- 125000004429 atom Chemical group 0.000 description 10
- 244000309464 bull Species 0.000 description 10
- 230000008859 change Effects 0.000 description 10
- 239000012458 free base Substances 0.000 description 10
- 238000003780 insertion Methods 0.000 description 10
- 230000037431 insertion Effects 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- NIEBHDXUIJSHSL-UHFFFAOYSA-N 4-iodobenzaldehyde Chemical compound IC1=CC=C(C=O)C=C1 NIEBHDXUIJSHSL-UHFFFAOYSA-N 0.000 description 9
- PIMQQGJMDMAZGT-UHFFFAOYSA-N 4-methylthiobenzaldehyde Chemical compound CC1=CC=C(C=S)C=C1 PIMQQGJMDMAZGT-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 9
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229910007340 Zn(OAc)2.2H2O Inorganic materials 0.000 description 9
- 238000010276 construction Methods 0.000 description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 9
- 125000006239 protecting group Chemical group 0.000 description 9
- 239000002356 single layer Substances 0.000 description 9
- 238000001542 size-exclusion chromatography Methods 0.000 description 9
- 150000003462 sulfoxides Chemical class 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- BEAZKUGSCHFXIQ-UHFFFAOYSA-L zinc;diacetate;dihydrate Chemical compound O.O.[Zn+2].CC([O-])=O.CC([O-])=O BEAZKUGSCHFXIQ-UHFFFAOYSA-L 0.000 description 9
- 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 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 230000006870 function Effects 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- 230000003287 optical effect Effects 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 230000002441 reversible effect Effects 0.000 description 8
- 238000001228 spectrum Methods 0.000 description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 7
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 7
- 239000007983 Tris buffer Substances 0.000 description 7
- 125000002091 cationic group Chemical group 0.000 description 7
- 238000002484 cyclic voltammetry Methods 0.000 description 7
- 239000004205 dimethyl polysiloxane Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 230000005518 electrochemistry Effects 0.000 description 7
- 238000005516 engineering process Methods 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 239000010502 orange oil Substances 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 7
- 239000000523 sample Substances 0.000 description 7
- 239000010944 silver (metal) Substances 0.000 description 7
- 238000006467 substitution reaction Methods 0.000 description 7
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 6
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 6
- 235000019502 Orange oil Nutrition 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 230000006399 behavior Effects 0.000 description 6
- 230000008901 benefit Effects 0.000 description 6
- 150000003935 benzaldehydes Chemical class 0.000 description 6
- 239000013522 chelant Substances 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- WWXKNUYLTWOLJS-UHFFFAOYSA-N cyclopenta-1,3-diene (4-cyclopenta-2,4-dien-1-ylphenyl)methanol iron(2+) Chemical compound [Fe++].c1cc[cH-]c1.OCc1ccc(cc1)-[c-]1cccc1 WWXKNUYLTWOLJS-UHFFFAOYSA-N 0.000 description 6
- URMNZKPDEPNPBH-UHFFFAOYSA-N cyclopenta-1,3-diene 1-cyclopenta-2,4-dien-1-yl-4-iodobenzene iron(2+) Chemical compound [Fe++].c1cc[cH-]c1.Ic1ccc(cc1)-[c-]1cccc1 URMNZKPDEPNPBH-UHFFFAOYSA-N 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- 238000001514 detection method Methods 0.000 description 6
- 238000002848 electrochemical method Methods 0.000 description 6
- 239000003792 electrolyte Substances 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 6
- FRIHLTKQZGLODW-UHFFFAOYSA-N s-(2,3,5,6-tetrafluoro-4-formylphenyl) ethanethioate Chemical compound CC(=O)SC1=C(F)C(F)=C(C=O)C(F)=C1F FRIHLTKQZGLODW-UHFFFAOYSA-N 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- 239000010703 silicon Substances 0.000 description 6
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 6
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 5
- 125000005808 2,4,6-trimethoxyphenyl group Chemical group [H][#6]-1=[#6](-[#8]C([H])([H])[H])-[#6](-*)=[#6](-[#8]C([H])([H])[H])-[#6]([H])=[#6]-1-[#8]C([H])([H])[H] 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 5
- ODOQKWUKLACHRO-UHFFFAOYSA-N 2-[phenyl(1h-pyrrol-2-yl)methyl]-1h-pyrrole Chemical compound C1=CNC(C(C=2NC=CC=2)C=2C=CC=CC=2)=C1 ODOQKWUKLACHRO-UHFFFAOYSA-N 0.000 description 5
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 5
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 5
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 5
- 238000000862 absorption spectrum Methods 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 238000010511 deprotection reaction Methods 0.000 description 5
- 239000012954 diazonium Substances 0.000 description 5
- 150000001989 diazonium salts Chemical class 0.000 description 5
- DUYAAUVXQSMXQP-UHFFFAOYSA-N ethanethioic S-acid Chemical group CC(S)=O DUYAAUVXQSMXQP-UHFFFAOYSA-N 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 5
- 238000013467 fragmentation Methods 0.000 description 5
- 238000006062 fragmentation reaction Methods 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 230000003993 interaction Effects 0.000 description 5
- 238000004949 mass spectrometry Methods 0.000 description 5
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 230000001590 oxidative effect Effects 0.000 description 5
- 230000002093 peripheral effect Effects 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 238000001338 self-assembly Methods 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 description 5
- 239000012279 sodium borohydride Substances 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 238000010561 standard procedure Methods 0.000 description 5
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 5
- 230000005641 tunneling Effects 0.000 description 5
- LMSFUWKGADQXES-UHFFFAOYSA-N 2-[1h-pyrrol-2-yl-(2,4,6-trimethylphenyl)methyl]-1h-pyrrole Chemical compound CC1=CC(C)=CC(C)=C1C(C=1NC=CC=1)C1=CC=CN1 LMSFUWKGADQXES-UHFFFAOYSA-N 0.000 description 4
- OEPGAYXSRGROSQ-UHFFFAOYSA-N 3-(bromomethyl)benzaldehyde Chemical compound BrCC1=CC=CC(C=O)=C1 OEPGAYXSRGROSQ-UHFFFAOYSA-N 0.000 description 4
- ZRYZBQLXDKPBDU-UHFFFAOYSA-N 4-bromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C=C1 ZRYZBQLXDKPBDU-UHFFFAOYSA-N 0.000 description 4
- VLVCDUSVTXIWGW-UHFFFAOYSA-N 4-iodoaniline Chemical compound NC1=CC=C(I)C=C1 VLVCDUSVTXIWGW-UHFFFAOYSA-N 0.000 description 4
- POXFXTSTVWDWIR-UHFFFAOYSA-N 4-iodobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C(I)C=C1 POXFXTSTVWDWIR-UHFFFAOYSA-N 0.000 description 4
- FQAAHIANZKDASD-UHFFFAOYSA-N 5-(6-bromohexyl)cyclopenta-1,3-diene;cyclopenta-1,3-diene;iron(2+) Chemical compound [Fe+2].C=1C=C[CH-]C=1.BrCCCCCC[C-]1C=CC=C1 FQAAHIANZKDASD-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 229920000557 Nafion® Polymers 0.000 description 4
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 229910052804 chromium Inorganic materials 0.000 description 4
- 239000011651 chromium Substances 0.000 description 4
- 238000004891 communication Methods 0.000 description 4
- 238000003869 coulometry Methods 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- 238000003795 desorption Methods 0.000 description 4
- 238000006056 electrooxidation reaction Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000003818 flash chromatography Methods 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 238000011010 flushing procedure Methods 0.000 description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 4
- 238000010348 incorporation Methods 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 238000005304 joining Methods 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 238000005442 molecular electronic Methods 0.000 description 4
- 230000008520 organization Effects 0.000 description 4
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 230000002688 persistence Effects 0.000 description 4
- 230000002085 persistent effect Effects 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 4
- PIMFYYQSMFCNPA-UHFFFAOYSA-N s-(4-formylphenyl) ethanethioate Chemical compound CC(=O)SC1=CC=C(C=O)C=C1 PIMFYYQSMFCNPA-UHFFFAOYSA-N 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- DUYAAUVXQSMXQP-UHFFFAOYSA-M thioacetate Chemical compound CC([S-])=O DUYAAUVXQSMXQP-UHFFFAOYSA-M 0.000 description 4
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 4
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 4
- 239000004246 zinc acetate Substances 0.000 description 4
- KMUWQZASOXZENM-UHFFFAOYSA-N (3-formylphenyl)methyl thiocyanate Chemical compound O=CC1=CC=CC(CSC#N)=C1 KMUWQZASOXZENM-UHFFFAOYSA-N 0.000 description 3
- AXKGIPZJYUNAIW-UHFFFAOYSA-N (4-aminophenyl)methanol Chemical compound NC1=CC=C(CO)C=C1 AXKGIPZJYUNAIW-UHFFFAOYSA-N 0.000 description 3
- LFMWZTSOMGDDJU-UHFFFAOYSA-N 1,4-diiodobenzene Chemical compound IC1=CC=C(I)C=C1 LFMWZTSOMGDDJU-UHFFFAOYSA-N 0.000 description 3
- QJXCFMJTJYCLFG-UHFFFAOYSA-N 2,3,4,5,6-pentafluorobenzaldehyde Chemical compound FC1=C(F)C(F)=C(C=O)C(F)=C1F QJXCFMJTJYCLFG-UHFFFAOYSA-N 0.000 description 3
- NSGNKYKZWXKPRL-UHFFFAOYSA-N 2-(12-bromododecyl)cyclopenta-1,3-diene cyclopenta-1,3-diene iron(2+) Chemical compound [Fe++].c1cc[cH-]c1.BrCCCCCCCCCCCC[c-]1cccc1 NSGNKYKZWXKPRL-UHFFFAOYSA-N 0.000 description 3
- DHEJIZSVHGOKMJ-UHFFFAOYSA-N 2-ethenylbenzaldehyde Chemical compound C=CC1=CC=CC=C1C=O DHEJIZSVHGOKMJ-UHFFFAOYSA-N 0.000 description 3
- QBFNGLBSVFKILI-UHFFFAOYSA-N 4-ethenylbenzaldehyde Chemical compound C=CC1=CC=C(C=O)C=C1 QBFNGLBSVFKILI-UHFFFAOYSA-N 0.000 description 3
- MMXRRNUXCHUHOE-UHFFFAOYSA-N 7-bromoheptan-1-ol Chemical compound OCCCCCCCBr MMXRRNUXCHUHOE-UHFFFAOYSA-N 0.000 description 3
- GQQZDMZVXIHHEW-UHFFFAOYSA-N C(C)(=O)SC1=CC=C(C=C1)C#CC1=CC=C(C=C1)[C-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2] Chemical compound C(C)(=O)SC1=CC=C(C=C1)C#CC1=CC=C(C=C1)[C-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2] GQQZDMZVXIHHEW-UHFFFAOYSA-N 0.000 description 3
- 101100219382 Caenorhabditis elegans cah-2 gene Proteins 0.000 description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 108020004414 DNA Proteins 0.000 description 3
- 102000053602 DNA Human genes 0.000 description 3
- 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 3
- DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 238000006254 arylation reaction Methods 0.000 description 3
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical compound C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 239000000919 ceramic Substances 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000006880 cross-coupling reaction Methods 0.000 description 3
- 230000002950 deficient Effects 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 238000002408 directed self-assembly Methods 0.000 description 3
- 150000002019 disulfides Chemical class 0.000 description 3
- 238000010265 fast atom bombardment Methods 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 238000002189 fluorescence spectrum Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 229910052747 lanthanoid Inorganic materials 0.000 description 3
- 150000002602 lanthanoids Chemical class 0.000 description 3
- 238000000608 laser ablation Methods 0.000 description 3
- 238000006138 lithiation reaction Methods 0.000 description 3
- 238000001459 lithography Methods 0.000 description 3
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 3
- KIQQAJNFBLKFPO-UHFFFAOYSA-N magnesium;porphyrin-22,23-diide Chemical group [Mg+2].[N-]1C(C=C2[N-]C(=CC3=NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 KIQQAJNFBLKFPO-UHFFFAOYSA-N 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 229940117969 neopentyl glycol Drugs 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 238000010791 quenching Methods 0.000 description 3
- 230000000171 quenching effect Effects 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 3
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical group SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- 230000000007 visual effect Effects 0.000 description 3
- WXIBFNLLGAPNSJ-UHFFFAOYSA-N (2-formylphenyl) thiocyanate Chemical compound O=CC1=CC=CC=C1SC#N WXIBFNLLGAPNSJ-UHFFFAOYSA-N 0.000 description 2
- QIVJSBXFACIFBL-UHFFFAOYSA-N 1-(bromomethyl)-4-cyclopenta-2,4-dien-1-ylbenzene cyclopenta-1,3-diene iron(2+) Chemical compound [Fe++].c1cc[cH-]c1.BrCc1ccc(cc1)-[c-]1cccc1 QIVJSBXFACIFBL-UHFFFAOYSA-N 0.000 description 2
- BQTRMYJYYNQQGK-UHFFFAOYSA-N 1-(bromomethyl)-4-iodobenzene Chemical compound BrCC1=CC=C(I)C=C1 BQTRMYJYYNQQGK-UHFFFAOYSA-N 0.000 description 2
- LOTKRQAVGJMPNV-UHFFFAOYSA-N 1-fluoro-2,4-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C([N+]([O-])=O)=C1 LOTKRQAVGJMPNV-UHFFFAOYSA-N 0.000 description 2
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 2
- CRBZVDLXAIFERF-UHFFFAOYSA-N 2,4,6-trimethoxybenzaldehyde Chemical compound COC1=CC(OC)=C(C=O)C(OC)=C1 CRBZVDLXAIFERF-UHFFFAOYSA-N 0.000 description 2
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 2
- 239000001431 2-methylbenzaldehyde Substances 0.000 description 2
- RGUXEWWHSQGVRZ-UHFFFAOYSA-N 3,3-diethoxyprop-1-yne Chemical compound CCOC(C#C)OCC RGUXEWWHSQGVRZ-UHFFFAOYSA-N 0.000 description 2
- HZBWOZJDPPOMOM-UHFFFAOYSA-N 3,5-ditert-butylbenzoyl chloride Chemical compound CC(C)(C)C1=CC(C(Cl)=O)=CC(C(C)(C)C)=C1 HZBWOZJDPPOMOM-UHFFFAOYSA-N 0.000 description 2
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 2
- CHTZIDLXGXGNMA-UHFFFAOYSA-N 4-(2-trimethylsilylethynyl)aniline Chemical compound C[Si](C)(C)C#CC1=CC=C(N)C=C1 CHTZIDLXGXGNMA-UHFFFAOYSA-N 0.000 description 2
- XYPVBKDHERGKJG-UHFFFAOYSA-N 4-(bromomethyl)benzaldehyde Chemical compound BrCC1=CC=C(C=O)C=C1 XYPVBKDHERGKJG-UHFFFAOYSA-N 0.000 description 2
- MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 description 2
- IKZUTVQEBGHQJA-UHFFFAOYSA-N 4-iodobenzenethiol Chemical compound SC1=CC=C(I)C=C1 IKZUTVQEBGHQJA-UHFFFAOYSA-N 0.000 description 2
- WNLMYNASWOULQY-UHFFFAOYSA-N 4-tert-butylbenzoyl chloride Chemical compound CC(C)(C)C1=CC=C(C(Cl)=O)C=C1 WNLMYNASWOULQY-UHFFFAOYSA-N 0.000 description 2
- PCVRSXXPGXRVEZ-UHFFFAOYSA-N 9-(chloromethyl)anthracene Chemical compound C1=CC=C2C(CCl)=C(C=CC=C3)C3=CC2=C1 PCVRSXXPGXRVEZ-UHFFFAOYSA-N 0.000 description 2
- 229910000497 Amalgam Inorganic materials 0.000 description 2
- 241001120493 Arene Species 0.000 description 2
- RHFUAGPQOOJXBQ-UHFFFAOYSA-N CC([S+]=CC1=CC=CC=C1)=O Chemical compound CC([S+]=CC1=CC=CC=C1)=O RHFUAGPQOOJXBQ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 235000008694 Humulus lupulus Nutrition 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 101100010166 Mus musculus Dok3 gene Proteins 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 238000001069 Raman spectroscopy Methods 0.000 description 2
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- CXDVQWISYFKBFZ-UHFFFAOYSA-N [N]1C2=CC=C1C=C(N1)C=C(C#C)C1=CC([N]1)=CC=C1C=C(N1)C=CC1=C2 Chemical compound [N]1C2=CC=C1C=C(N1)C=C(C#C)C1=CC([N]1)=CC=C1C=C(N1)C=CC1=C2 CXDVQWISYFKBFZ-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 150000001347 alkyl bromides Chemical class 0.000 description 2
- 150000001356 alkyl thiols Chemical group 0.000 description 2
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000004082 amperometric method Methods 0.000 description 2
- 150000001504 aryl thiols Chemical group 0.000 description 2
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 150000001649 bromium compounds Chemical class 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 239000002322 conducting polymer Substances 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 230000021615 conjugation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- MESJGSCMTRFPRP-UHFFFAOYSA-N cyclopenta-1,3-diene (2-ethynylcyclopenta-2,4-dien-1-yl)benzene iron(2+) Chemical compound [Fe++].c1cc[cH-]c1.C#Cc1ccc[c-]1-c1ccccc1 MESJGSCMTRFPRP-UHFFFAOYSA-N 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000007324 demetalation reaction Methods 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- FPULFENIJDPZBX-UHFFFAOYSA-N ethyl 2-isocyanoacetate Chemical compound CCOC(=O)C[N+]#[C-] FPULFENIJDPZBX-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 238000002847 impedance measurement Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- BLQJIBCZHWBKSL-UHFFFAOYSA-L magnesium iodide Chemical compound [Mg+2].[I-].[I-] BLQJIBCZHWBKSL-UHFFFAOYSA-L 0.000 description 2
- 229910001641 magnesium iodide Inorganic materials 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 238000005459 micromachining Methods 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 2
- 230000005693 optoelectronics Effects 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 238000005691 oxidative coupling reaction Methods 0.000 description 2
- WYURNTSHIVDZCO-SVYQBANQSA-N oxolane-d8 Chemical compound [2H]C1([2H])OC([2H])([2H])C([2H])([2H])C1([2H])[2H] WYURNTSHIVDZCO-SVYQBANQSA-N 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 238000004806 packaging method and process Methods 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 230000037361 pathway Effects 0.000 description 2
- 230000010363 phase shift Effects 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000011970 polystyrene sulfonate Substances 0.000 description 2
- 229960002796 polystyrene sulfonate Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229940116357 potassium thiocyanate Drugs 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000004237 preparative chromatography Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 238000007342 radical addition reaction Methods 0.000 description 2
- 150000005839 radical cations Chemical class 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- SUKCGDCKAJESMC-UHFFFAOYSA-N s-(4-ethynylphenyl) ethanethioate Chemical group CC(=O)SC1=CC=C(C#C)C=C1 SUKCGDCKAJESMC-UHFFFAOYSA-N 0.000 description 2
- RHMVTJDRMGRHTJ-UHFFFAOYSA-N s-(4-formylphenyl) n-ethylcarbamothioate Chemical compound CCNC(=O)SC1=CC=C(C=O)C=C1 RHMVTJDRMGRHTJ-UHFFFAOYSA-N 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 238000004365 square wave voltammetry Methods 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 239000003774 sulfhydryl reagent Substances 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- ACOOSTZBTYEGER-UHFFFAOYSA-N thiobenzaldehyde Chemical compound S=CC1=CC=CC=C1 ACOOSTZBTYEGER-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 description 1
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
- FZGVVJAMZPDGOX-UHFFFAOYSA-N (4-formylphenyl) thiocyanate Chemical compound O=CC1=CC=C(SC#N)C=C1 FZGVVJAMZPDGOX-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WACNXHCZHTVBJM-UHFFFAOYSA-N 1,2,3,4,5-pentafluorobenzene Chemical group FC1=CC(F)=C(F)C(F)=C1F WACNXHCZHTVBJM-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- GQFITODJWOIYPF-UHFFFAOYSA-N 1-(bromomethyl)-2-iodobenzene Chemical compound BrCC1=CC=CC=C1I GQFITODJWOIYPF-UHFFFAOYSA-N 0.000 description 1
- WDKIARLEQFHVKC-UHFFFAOYSA-N 1-cyclopenta-1,3-dien-1-ylethanone;iron(2+) Chemical compound [Fe+2].CC(=O)C1=CC=C[CH-]1.CC(=O)C1=CC=C[CH-]1 WDKIARLEQFHVKC-UHFFFAOYSA-N 0.000 description 1
- KGNQDBQYEBMPFZ-UHFFFAOYSA-N 1-fluoro-4-iodobenzene Chemical compound FC1=CC=C(I)C=C1 KGNQDBQYEBMPFZ-UHFFFAOYSA-N 0.000 description 1
- QHGJUJAJOZPFJL-UHFFFAOYSA-N 12,13,23-tris(2,3,4,5,6-pentafluorophenyl)-21h-porphyrin Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1C(C1=CC2=CC=C([N]2)C=C2C=CC(N2)=CC2=CC=C([N]2)C=C2N1C=1C(=C(F)C(F)=C(F)C=1F)F)=C2C1=C(F)C(F)=C(F)C(F)=C1F QHGJUJAJOZPFJL-UHFFFAOYSA-N 0.000 description 1
- AAZZRSZIFFFEEE-UHFFFAOYSA-N 12-bromododecanoyl chloride Chemical compound ClC(=O)CCCCCCCCCCCBr AAZZRSZIFFFEEE-UHFFFAOYSA-N 0.000 description 1
- OHOKQIKLENCZIP-UHFFFAOYSA-N 16-bromohexadecanoyl chloride Chemical compound ClC(=O)CCCCCCCCCCCCCCCBr OHOKQIKLENCZIP-UHFFFAOYSA-N 0.000 description 1
- JPRFASFEBMSNDY-UHFFFAOYSA-N 2,3,5,6-tetrafluoro-4-sulfanylbenzaldehyde Chemical compound FC1=C(F)C(C=O)=C(F)C(F)=C1S JPRFASFEBMSNDY-UHFFFAOYSA-N 0.000 description 1
- GGSGPPFRVNQBCV-UHFFFAOYSA-N 2,5-bis(1h-pyrrol-2-ylmethyl)-1h-pyrrole Chemical compound C=1C=C(CC=2NC=CC=2)NC=1CC1=CC=CN1 GGSGPPFRVNQBCV-UHFFFAOYSA-N 0.000 description 1
- VUOZSTRHTFWCGA-UHFFFAOYSA-N 2-(16-bromohexadecyl)cyclopenta-1,3-diene cyclopenta-1,3-diene iron(2+) Chemical compound [Fe++].c1cc[cH-]c1.BrCCCCCCCCCCCCCCCC[c-]1cccc1 VUOZSTRHTFWCGA-UHFFFAOYSA-N 0.000 description 1
- QZMPLZMDCNBPTB-UHFFFAOYSA-N 2-(4-bromophenyl)-5,5-dimethyl-1,3-dioxane Chemical compound O1CC(C)(C)COC1C1=CC=C(Br)C=C1 QZMPLZMDCNBPTB-UHFFFAOYSA-N 0.000 description 1
- WOOFAKCCTQIPLK-UHFFFAOYSA-N 2-(4-iodophenyl)ethynyl-trimethylsilane Chemical compound C[Si](C)(C)C#CC1=CC=C(I)C=C1 WOOFAKCCTQIPLK-UHFFFAOYSA-N 0.000 description 1
- WWKKTHALZAYYAI-UHFFFAOYSA-N 2-iodobenzaldehyde Chemical compound IC1=CC=CC=C1C=O WWKKTHALZAYYAI-UHFFFAOYSA-N 0.000 description 1
- NCTSLPBQVXUAHR-UHFFFAOYSA-N 3,5-ditert-butylbenzoic acid Chemical compound CC(C)(C)C1=CC(C(O)=O)=CC(C(C)(C)C)=C1 NCTSLPBQVXUAHR-UHFFFAOYSA-N 0.000 description 1
- CVKOOKPNCVYHNY-UHFFFAOYSA-N 3-(bromomethyl)benzonitrile Chemical compound BrCC1=CC=CC(C#N)=C1 CVKOOKPNCVYHNY-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- RZODAQZAFOBFLS-UHFFFAOYSA-N 3-iodobenzaldehyde Chemical compound IC1=CC=CC(C=O)=C1 RZODAQZAFOBFLS-UHFFFAOYSA-N 0.000 description 1
- LTMDHKBCEWECPX-UHFFFAOYSA-N 4-(5,5-dimethyl-1,3-dioxan-2-yl)benzenethiol Chemical compound O1CC(C)(C)COC1C1=CC=C(S)C=C1 LTMDHKBCEWECPX-UHFFFAOYSA-N 0.000 description 1
- UMLFTCYAQPPZER-UHFFFAOYSA-N 4-(bromomethyl)benzonitrile Chemical compound BrCC1=CC=C(C#N)C=C1 UMLFTCYAQPPZER-UHFFFAOYSA-N 0.000 description 1
- NRLPPGBADQVXSJ-UHFFFAOYSA-N 4-sulfanylbenzaldehyde Chemical compound SC1=CC=C(C=O)C=C1 NRLPPGBADQVXSJ-UHFFFAOYSA-N 0.000 description 1
- VFBWAZDYOAXHLK-UHFFFAOYSA-N 5,5-dimethyl-2-(4-prop-2-enylphenyl)-1,3-dioxane Chemical compound O1CC(C)(C)COC1C1=CC=C(CC=C)C=C1 VFBWAZDYOAXHLK-UHFFFAOYSA-N 0.000 description 1
- HBPVGJGBRWIVSX-UHFFFAOYSA-N 6-bromohexanoyl chloride Chemical compound ClC(=O)CCCCCBr HBPVGJGBRWIVSX-UHFFFAOYSA-N 0.000 description 1
- UXHBEJHWPUSRJH-UHFFFAOYSA-N 7-bromoheptanal Chemical compound BrCCCCCCC=O UXHBEJHWPUSRJH-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 238000012935 Averaging Methods 0.000 description 1
- 108010082845 Bacteriorhodopsins Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- 241000252506 Characiformes Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 238000006214 Clemmensen reduction reaction Methods 0.000 description 1
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 1
- 241001481833 Coryphaena hippurus Species 0.000 description 1
- 229910052692 Dysprosium Inorganic materials 0.000 description 1
- 238000004435 EPR spectroscopy Methods 0.000 description 1
- 229910052691 Erbium Inorganic materials 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 229910052689 Holmium Inorganic materials 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229910052765 Lutetium Inorganic materials 0.000 description 1
- XOGTZOOQQBDUSI-UHFFFAOYSA-M Mesna Chemical compound [Na+].[O-]S(=O)(=O)CCS XOGTZOOQQBDUSI-UHFFFAOYSA-M 0.000 description 1
- 238000006957 Michael reaction Methods 0.000 description 1
- 229910052779 Neodymium Inorganic materials 0.000 description 1
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 229910052777 Praseodymium Inorganic materials 0.000 description 1
- 101000984527 Pseudomonas putida Benzene 1,2-dioxygenase system ferredoxin subunit Proteins 0.000 description 1
- 229910019020 PtO2 Inorganic materials 0.000 description 1
- 238000006778 Pummerer Sulfoxide rearrangement reaction Methods 0.000 description 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
- 229910052776 Thorium Inorganic materials 0.000 description 1
- 229910052775 Thulium Inorganic materials 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- 229910007339 Zn(OAc)2 Inorganic materials 0.000 description 1
- MPRAJAJNLRLDDL-UHFFFAOYSA-N [C-]1(C=CC=C1)C(=O)CCCCCBr.[CH-]1C=CC=C1.[Fe+2] Chemical compound [C-]1(C=CC=C1)C(=O)CCCCCBr.[CH-]1C=CC=C1.[Fe+2] MPRAJAJNLRLDDL-UHFFFAOYSA-N 0.000 description 1
- FRCCXXAYBKWTEJ-UHFFFAOYSA-N [C-]1(C=CC=C1)C(=O)CCCCCCCCCCCCCCCBr.[CH-]1C=CC=C1.[Fe+2] Chemical compound [C-]1(C=CC=C1)C(=O)CCCCCCCCCCCCCCCBr.[CH-]1C=CC=C1.[Fe+2] FRCCXXAYBKWTEJ-UHFFFAOYSA-N 0.000 description 1
- IHOMKOPTBSYOCI-UHFFFAOYSA-N [Fe].c1cccc1.c1ccc(c1)C1=CC=CC=C1 Chemical compound [Fe].c1cccc1.c1ccc(c1)C1=CC=CC=C1 IHOMKOPTBSYOCI-UHFFFAOYSA-N 0.000 description 1
- OXLVMVIUBXHTSA-UHFFFAOYSA-N [Mg].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 Chemical class [Mg].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 OXLVMVIUBXHTSA-UHFFFAOYSA-N 0.000 description 1
- GBRTWESJXDZQRS-UHFFFAOYSA-N [N]1C2=CC=C1C=C(N1)C=C(I)C1=CC([N]1)=CC=C1C=C(N1)C=CC1=C2 Chemical compound [N]1C2=CC=C1C=C(N1)C=C(I)C1=CC([N]1)=CC=C1C=C(N1)C=CC1=C2 GBRTWESJXDZQRS-UHFFFAOYSA-N 0.000 description 1
- BVPRUAZVDOHSHP-UHFFFAOYSA-N [S-][S-].[Zn+2] Chemical compound [S-][S-].[Zn+2] BVPRUAZVDOHSHP-UHFFFAOYSA-N 0.000 description 1
- 238000004847 absorption spectroscopy Methods 0.000 description 1
- 125000004036 acetal group Chemical group 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000004964 aerogel Substances 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 125000002355 alkine group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001413 amino acids Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
- 230000000712 assembly Effects 0.000 description 1
- 229910052789 astatine Inorganic materials 0.000 description 1
- RYXHOMYVWAEKHL-UHFFFAOYSA-N astatine atom Chemical compound [At] RYXHOMYVWAEKHL-UHFFFAOYSA-N 0.000 description 1
- 238000004630 atomic force microscopy Methods 0.000 description 1
- 230000003190 augmentative effect Effects 0.000 description 1
- 150000004036 bacteriochlorins Chemical class 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 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
- 230000001588 bifunctional effect Effects 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 239000005388 borosilicate glass Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 230000003139 buffering effect 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
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- SURLGNKAQXKNSP-DBLYXWCISA-N chlorin Chemical compound C\1=C/2\N/C(=C\C3=N/C(=C\C=4NC(/C=C\5/C=CC/1=N/5)=CC=4)/C=C3)/CC\2 SURLGNKAQXKNSP-DBLYXWCISA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000004035 chlorins Chemical class 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 238000000970 chrono-amperometry Methods 0.000 description 1
- 238000001567 chrono-coulometry Methods 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000001427 coherent effect Effects 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 230000001268 conjugating effect Effects 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- PDZKZMQQDCHTNF-UHFFFAOYSA-M copper(1+);thiocyanate Chemical compound [Cu+].[S-]C#N PDZKZMQQDCHTNF-UHFFFAOYSA-M 0.000 description 1
- 150000004039 corphins Chemical class 0.000 description 1
- WUPRCGRRQUZFAB-DEGKJRJSSA-N corrin Chemical compound N1C2CC\C1=C\C(CC/1)=N\C\1=C/C(CC\1)=N/C/1=C\C1=NC2CC1 WUPRCGRRQUZFAB-DEGKJRJSSA-N 0.000 description 1
- LYNARWYQOUZXDY-UHFFFAOYSA-N corrole Chemical compound N1C(C=C2NC(=CC=3NC4=CC=3)C=C2)=CC=C1C=C1C=CC4=N1 LYNARWYQOUZXDY-UHFFFAOYSA-N 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- NHXNTSUKOSOBSA-UHFFFAOYSA-N cyclopenta-1,3-diene 1-cyclopenta-2,4-dien-1-yl-4-ethynylbenzene iron(2+) Chemical compound [Fe++].c1cc[cH-]c1.C#Cc1ccc(cc1)-[c-]1cccc1 NHXNTSUKOSOBSA-UHFFFAOYSA-N 0.000 description 1
- ALZSEUYSCHYXLH-UHFFFAOYSA-N cyclopenta-1,3-diene 2-(4-cyclopenta-2,4-dien-1-ylphenyl)ethynyl-trimethylsilane iron(2+) Chemical compound [Fe++].c1cc[cH-]c1.C[Si](C)(C)C#Cc1ccc(cc1)-[c-]1cccc1 ALZSEUYSCHYXLH-UHFFFAOYSA-N 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000001736 differential pulse polarography Methods 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000003487 electrochemical reaction Methods 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 238000001493 electron microscopy Methods 0.000 description 1
- 230000005274 electronic transitions Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000004993 emission spectroscopy Methods 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- BTIJJDXEELBZFS-QDUVMHSLSA-K hemin Chemical compound CC1=C(CCC(O)=O)C(C=C2C(CCC(O)=O)=C(C)\C(N2[Fe](Cl)N23)=C\4)=N\C1=C/C2=C(C)C(C=C)=C3\C=C/1C(C)=C(C=C)C/4=N\1 BTIJJDXEELBZFS-QDUVMHSLSA-K 0.000 description 1
- 229940025294 hemin Drugs 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 238000009815 homocoupling reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- ARRNBPCNZJXHRJ-UHFFFAOYSA-M hydron;tetrabutylazanium;phosphate Chemical compound OP(O)([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC ARRNBPCNZJXHRJ-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 238000001453 impedance spectrum Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000010365 information processing Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- JCIVIRQSXLTMEF-UHFFFAOYSA-N iodoethyne Chemical compound IC#C JCIVIRQSXLTMEF-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000004037 isobacteriochlorins Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- 238000004989 laser desorption mass spectroscopy Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 238000004502 linear sweep voltammetry Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000013507 mapping Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229960004635 mesna Drugs 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 238000001393 microlithography Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 230000005298 paramagnetic effect Effects 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 230000029553 photosynthesis Effects 0.000 description 1
- 238000010672 photosynthesis Methods 0.000 description 1
- 229920001197 polyacetylene Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- VCRBUDCZLSQJPZ-UHFFFAOYSA-N porphyrinogen Chemical compound C1C(N2)=CC=C2CC(N2)=CC=C2CC(N2)=CC=C2CC2=CC=C1N2 VCRBUDCZLSQJPZ-UHFFFAOYSA-N 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 108090000765 processed proteins & peptides Chemical group 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- IJNJLGFTSIAHEA-UHFFFAOYSA-N prop-2-ynal Chemical compound O=CC#C IJNJLGFTSIAHEA-UHFFFAOYSA-N 0.000 description 1
- 238000000083 pulse voltammetry Methods 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 230000002468 redox effect Effects 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- DGVGXTJOCSDXEW-UHFFFAOYSA-N s-(7-oxoheptyl) ethanethioate Chemical compound CC(=O)SCCCCCCC=O DGVGXTJOCSDXEW-UHFFFAOYSA-N 0.000 description 1
- LWKSUVIKHPGKJJ-UHFFFAOYSA-N s-[(3-formylphenyl)methyl] ethanethioate Chemical compound CC(=O)SCC1=CC=CC(C=O)=C1 LWKSUVIKHPGKJJ-UHFFFAOYSA-N 0.000 description 1
- XEOGHHBZYSIDIG-UHFFFAOYSA-N s-[(4-ethynylphenyl)methyl] ethanethioate Chemical group CC(=O)SCC1=CC=C(C#C)C=C1 XEOGHHBZYSIDIG-UHFFFAOYSA-N 0.000 description 1
- GBKJZXDXGKMGLM-UHFFFAOYSA-N s-[(4-formylphenyl)methyl] ethanethioate Chemical compound CC(=O)SCC1=CC=C(C=O)C=C1 GBKJZXDXGKMGLM-UHFFFAOYSA-N 0.000 description 1
- VFDFVTDPMDLFOX-UHFFFAOYSA-N s-[(4-iodophenyl)methyl] ethanethioate Chemical compound CC(=O)SCC1=CC=C(I)C=C1 VFDFVTDPMDLFOX-UHFFFAOYSA-N 0.000 description 1
- DUIFYWOVCREUNY-UHFFFAOYSA-N s-[4-(2-trimethylsilylethynyl)phenyl] ethanethioate Chemical compound CC(=O)SC1=CC=C(C#C[Si](C)(C)C)C=C1 DUIFYWOVCREUNY-UHFFFAOYSA-N 0.000 description 1
- CDAFNVVZFVZPIR-UHFFFAOYSA-N s-[4-(3-oxoprop-1-ynyl)phenyl] ethanethioate Chemical compound CC(=O)SC1=CC=C(C#CC=O)C=C1 CDAFNVVZFVZPIR-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000011232 storage material Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000003115 supporting electrolyte Substances 0.000 description 1
- 238000010408 sweeping Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 238000006719 thioacetalization reaction Methods 0.000 description 1
- 150000003567 thiocyanates Chemical class 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- VJMQFIRIMMSSRW-UHFFFAOYSA-N trimethyl(phenylsulfanyl)silane Chemical compound C[Si](C)(C)SC1=CC=CC=C1 VJMQFIRIMMSSRW-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
- 238000002460 vibrational spectroscopy Methods 0.000 description 1
- 238000001845 vibrational spectrum Methods 0.000 description 1
- 238000001075 voltammogram Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- KECBRSWRLXVGIW-UHFFFAOYSA-N zinc S-[4-[10,20-bis(3,5-ditert-butylphenyl)-21,23-dihydroporphyrin-5-yl]phenyl] ethanethioate Chemical compound C(C)(C)(C)C=1C=C(C=C(C1)C(C)(C)C)C=1C=2C=CC(=C(C3=CC=C(N3)C(=C3C=CC(C=C4C=CC1N4)=N3)C3=CC(=CC(=C3)C(C)(C)C)C(C)(C)C)C3=CC=C(C=C3)SC(C)=O)N2.[Zn+2] KECBRSWRLXVGIW-UHFFFAOYSA-N 0.000 description 1
- DJWUNCQRNNEAKC-UHFFFAOYSA-L zinc acetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O DJWUNCQRNNEAKC-UHFFFAOYSA-L 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y10/00—Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
- C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic Table
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11C—STATIC STORES
- G11C11/00—Digital stores characterised by the use of particular electric or magnetic storage elements; Storage elements therefor
- G11C11/56—Digital stores characterised by the use of particular electric or magnetic storage elements; Storage elements therefor using storage elements with more than two stable states represented by steps, e.g. of voltage, current, phase, frequency
- G11C11/5664—Digital stores characterised by the use of particular electric or magnetic storage elements; Storage elements therefor using storage elements with more than two stable states represented by steps, e.g. of voltage, current, phase, frequency using organic memory material storage elements
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11C—STATIC STORES
- G11C13/00—Digital stores characterised by the use of storage elements not covered by groups G11C11/00, G11C23/00, or G11C25/00
- G11C13/0002—Digital stores characterised by the use of storage elements not covered by groups G11C11/00, G11C23/00, or G11C25/00 using resistive RAM [RRAM] elements
- G11C13/0009—RRAM elements whose operation depends upon chemical change
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11C—STATIC STORES
- G11C13/00—Digital stores characterised by the use of storage elements not covered by groups G11C11/00, G11C23/00, or G11C25/00
- G11C13/0002—Digital stores characterised by the use of storage elements not covered by groups G11C11/00, G11C23/00, or G11C25/00 using resistive RAM [RRAM] elements
- G11C13/0009—RRAM elements whose operation depends upon chemical change
- G11C13/0014—RRAM elements whose operation depends upon chemical change comprising cells based on organic memory material
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11C—STATIC STORES
- G11C13/00—Digital stores characterised by the use of storage elements not covered by groups G11C11/00, G11C23/00, or G11C25/00
- G11C13/0002—Digital stores characterised by the use of storage elements not covered by groups G11C11/00, G11C23/00, or G11C25/00 using resistive RAM [RRAM] elements
- G11C13/0009—RRAM elements whose operation depends upon chemical change
- G11C13/0014—RRAM elements whose operation depends upon chemical change comprising cells based on organic memory material
- G11C13/0016—RRAM elements whose operation depends upon chemical change comprising cells based on organic memory material comprising polymers
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11C—STATIC STORES
- G11C13/00—Digital stores characterised by the use of storage elements not covered by groups G11C11/00, G11C23/00, or G11C25/00
- G11C13/0002—Digital stores characterised by the use of storage elements not covered by groups G11C11/00, G11C23/00, or G11C25/00 using resistive RAM [RRAM] elements
- G11C13/0021—Auxiliary circuits
- G11C13/0069—Writing or programming circuits or methods
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/701—Organic molecular electronic devices
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K19/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic element specially adapted for rectifying, amplifying, oscillating or switching, covered by group H10K10/00
-
- 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
- H10K85/30—Coordination compounds
-
- 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
- H10K85/30—Coordination compounds
- H10K85/311—Phthalocyanine
-
- 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
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B9/00—Recording or reproducing using a method not covered by one of the main groups G11B3/00 - G11B7/00; Record carriers therefor
- G11B9/12—Recording or reproducing using a method not covered by one of the main groups G11B3/00 - G11B7/00; Record carriers therefor using near-field interactions; Record carriers therefor
- G11B9/14—Recording or reproducing using a method not covered by one of the main groups G11B3/00 - G11B7/00; Record carriers therefor using near-field interactions; Record carriers therefor using microscopic probe means, i.e. recording or reproducing by means directly associated with the tip of a microscopic electrical probe as used in Scanning Tunneling Microscopy [STM] or Atomic Force Microscopy [AFM] for inducing physical or electrical perturbations in a recording medium; Record carriers or media specially adapted for such transducing of information
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B9/00—Recording or reproducing using a method not covered by one of the main groups G11B3/00 - G11B7/00; Record carriers therefor
- G11B9/12—Recording or reproducing using a method not covered by one of the main groups G11B3/00 - G11B7/00; Record carriers therefor using near-field interactions; Record carriers therefor
- G11B9/14—Recording or reproducing using a method not covered by one of the main groups G11B3/00 - G11B7/00; Record carriers therefor using near-field interactions; Record carriers therefor using microscopic probe means, i.e. recording or reproducing by means directly associated with the tip of a microscopic electrical probe as used in Scanning Tunneling Microscopy [STM] or Atomic Force Microscopy [AFM] for inducing physical or electrical perturbations in a recording medium; Record carriers or media specially adapted for such transducing of information
- G11B9/1463—Record carriers for recording or reproduction involving the use of microscopic probe means
- G11B9/149—Record carriers for recording or reproduction involving the use of microscopic probe means characterised by the memorising material or structure
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11C—STATIC STORES
- G11C13/00—Digital stores characterised by the use of storage elements not covered by groups G11C11/00, G11C23/00, or G11C25/00
- G11C13/02—Digital stores characterised by the use of storage elements not covered by groups G11C11/00, G11C23/00, or G11C25/00 using elements whose operation depends upon chemical change
- G11C13/025—Digital stores characterised by the use of storage elements not covered by groups G11C11/00, G11C23/00, or G11C25/00 using elements whose operation depends upon chemical change using fullerenes, e.g. C60, or nanotubes, e.g. carbon or silicon nanotubes
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11C—STATIC STORES
- G11C13/00—Digital stores characterised by the use of storage elements not covered by groups G11C11/00, G11C23/00, or G11C25/00
- G11C13/0002—Digital stores characterised by the use of storage elements not covered by groups G11C11/00, G11C23/00, or G11C25/00 using resistive RAM [RRAM] elements
- G11C13/0021—Auxiliary circuits
- G11C13/0069—Writing or programming circuits or methods
- G11C2013/009—Write using potential difference applied between cell electrodes
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11C—STATIC STORES
- G11C2213/00—Indexing scheme relating to G11C13/00 for features not covered by this group
- G11C2213/10—Resistive cells; Technology aspects
- G11C2213/15—Current-voltage curve
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11C—STATIC STORES
- G11C2213/00—Indexing scheme relating to G11C13/00 for features not covered by this group
- G11C2213/70—Resistive array aspects
- G11C2213/77—Array wherein the memory element being directly connected to the bit lines and word lines without any access device being used
-
- 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
- H10K85/30—Coordination compounds
- H10K85/361—Polynuclear complexes, i.e. complexes comprising two or more metal centers
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Nanotechnology (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Theoretical Computer Science (AREA)
- Mathematical Physics (AREA)
- Computer Hardware Design (AREA)
- Composite Materials (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Semiconductor Memories (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/346,221 | 1999-07-01 | ||
| US09/346,221 US6208553B1 (en) | 1999-07-01 | 1999-07-01 | High density non-volatile memory device incorporating thiol-derivatized porphyrins |
| US09/346,228 US6381169B1 (en) | 1999-07-01 | 1999-07-01 | High density non-volatile memory device |
| US09/346,228 | 1999-07-01 | ||
| US09/484,394 US6324091B1 (en) | 2000-01-14 | 2000-01-14 | Tightly coupled porphyrin macrocycles for molecular memory storage |
| US09/484,394 | 2000-01-14 | ||
| PCT/US2000/017847 WO2001003126A2 (en) | 1999-07-01 | 2000-06-28 | High density non-volatile memory device |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2377671A1 CA2377671A1 (en) | 2001-01-11 |
| CA2377671C true CA2377671C (en) | 2011-01-04 |
Family
ID=27407734
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2377671A Expired - Fee Related CA2377671C (en) | 1999-07-01 | 2000-06-28 | High density non-volatile memory device |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US7042755B1 (enExample) |
| EP (1) | EP1210714A4 (enExample) |
| JP (1) | JP2003504839A (enExample) |
| AU (1) | AU764750B2 (enExample) |
| CA (1) | CA2377671C (enExample) |
| IL (2) | IL147119A0 (enExample) |
| NO (1) | NO20016420L (enExample) |
| WO (1) | WO2001003126A2 (enExample) |
Families Citing this family (64)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7207251B2 (en) | 1999-02-05 | 2007-04-24 | Hitachi Koki Co., Ltd. | Cutter with laser generator that irradiates cutting position on workpiece to facilitate alignment of blade with cutting position |
| US6381169B1 (en) | 1999-07-01 | 2002-04-30 | The Regents Of The University Of California | High density non-volatile memory device |
| EP1210714A4 (en) | 1999-07-01 | 2006-01-04 | Univ | HIGH DENSITY REMANENT MEMORY DEVICE |
| AU778378B2 (en) * | 2000-01-14 | 2004-12-02 | North Carolina State University | Substrates carrying polymers of linked sandwich coordination compounds and methods of use thereof |
| DE10061297C2 (de) | 2000-12-08 | 2003-05-28 | Siemens Ag | Verfahren zur Sturkturierung eines OFETs |
| DE10061299A1 (de) | 2000-12-08 | 2002-06-27 | Siemens Ag | Vorrichtung zur Feststellung und/oder Weiterleitung zumindest eines Umwelteinflusses, Herstellungsverfahren und Verwendung dazu |
| US7141299B2 (en) * | 2001-01-05 | 2006-11-28 | The Ohio State University Research Foundation | Electronic junction devices featuring redox electrodes |
| DE10105914C1 (de) | 2001-02-09 | 2002-10-10 | Siemens Ag | Organischer Feldeffekt-Transistor mit fotostrukturiertem Gate-Dielektrikum und ein Verfahren zu dessen Erzeugung |
| WO2002077633A1 (en) | 2001-03-23 | 2002-10-03 | The Regents Of The University Of California | Open circuit potential amperometry and voltammetry |
| EP1397809B1 (en) * | 2001-05-07 | 2007-06-27 | Advanced Micro Devices, Inc. | A memory device with a self-assembled polymer film and method of making the same |
| DE10151036A1 (de) | 2001-10-16 | 2003-05-08 | Siemens Ag | Isolator für ein organisches Elektronikbauteil |
| DE10151440C1 (de) | 2001-10-18 | 2003-02-06 | Siemens Ag | Organisches Elektronikbauteil, Verfahren zu seiner Herstellung und seine Verwendung |
| US7074519B2 (en) * | 2001-10-26 | 2006-07-11 | The Regents Of The University Of California | Molehole embedded 3-D crossbar architecture used in electrochemical molecular memory device |
| US7348206B2 (en) | 2001-10-26 | 2008-03-25 | The Regents Of The University Of California | Formation of self-assembled monolayers of redox SAMs on silicon for molecular memory applications |
| DE10160732A1 (de) | 2001-12-11 | 2003-06-26 | Siemens Ag | Organischer Feld-Effekt-Transistor mit verschobener Schwellwertspannung und Verwendung dazu |
| US6728129B2 (en) | 2002-02-19 | 2004-04-27 | The Regents Of The University Of California | Multistate triple-decker dyads in three distinct architectures for information storage applications |
| DE10212640B4 (de) | 2002-03-21 | 2004-02-05 | Siemens Ag | Logische Bauteile aus organischen Feldeffekttransistoren |
| GB0215375D0 (en) * | 2002-07-03 | 2002-08-14 | Univ Cambridge Tech | Organic-inorganic hybrid transistors |
| ATE355566T1 (de) | 2002-08-23 | 2006-03-15 | Polyic Gmbh & Co Kg | Organisches bauelement zum überspannungsschutz und dazugehörige schaltung |
| US6922350B2 (en) * | 2002-09-27 | 2005-07-26 | Intel Corporation | Reducing the effect of write disturbs in polymer memories |
| DE10253154A1 (de) | 2002-11-14 | 2004-05-27 | Siemens Ag | Messgerät zur Bestimmung eines Analyten in einer Flüssigkeitsprobe |
| DE50306538D1 (de) | 2002-11-19 | 2007-03-29 | Polyic Gmbh & Co Kg | Organische elektronische schaltung mit stukturierter halbleitender funktionsschicht und herstellungsverfahren dazu |
| DE10300521A1 (de) * | 2003-01-09 | 2004-07-22 | Siemens Ag | Organoresistiver Speicher |
| DE10302149A1 (de) | 2003-01-21 | 2005-08-25 | Siemens Ag | Verwendung leitfähiger Carbon-black/Graphit-Mischungen für die Herstellung von low-cost Elektronik |
| US6943054B2 (en) * | 2003-07-25 | 2005-09-13 | The Regents Of The University Of California | Attachment of organic molecules to group III, IV or V substrates |
| US7223628B2 (en) | 2003-07-25 | 2007-05-29 | The Regents Of The University Of California | High temperature attachment of organic molecules to substrates |
| DE10339036A1 (de) | 2003-08-25 | 2005-03-31 | Siemens Ag | Organisches elektronisches Bauteil mit hochaufgelöster Strukturierung und Herstellungsverfahren dazu |
| DE10340644B4 (de) | 2003-09-03 | 2010-10-07 | Polyic Gmbh & Co. Kg | Mechanische Steuerelemente für organische Polymerelektronik |
| US20050162895A1 (en) * | 2004-01-28 | 2005-07-28 | Kuhr Werner G. | Molecular memory arrays and devices |
| US7324385B2 (en) | 2004-01-28 | 2008-01-29 | Zettacore, Inc. | Molecular memory |
| US7307870B2 (en) | 2004-01-28 | 2007-12-11 | Zettacore, Inc. | Molecular memory devices and methods |
| US7358113B2 (en) | 2004-01-28 | 2008-04-15 | Zettacore, Inc. | Processing systems and methods for molecular memory |
| US7695756B2 (en) | 2004-04-29 | 2010-04-13 | Zettacore, Inc. | Systems, tools and methods for production of molecular memory |
| US7452572B1 (en) | 2004-03-11 | 2008-11-18 | The North Carolina State University | Procedure for preparing redox-active polymers on surfaces |
| CN102157691A (zh) * | 2004-04-29 | 2011-08-17 | 泽塔科尔公司 | 分子存储器和用于加工它的处理系统与方法 |
| EP1854160B1 (en) | 2005-02-10 | 2017-06-21 | Yeda Research And Development Co., Ltd. | Redox-active structures and devices utilizing the same |
| DE102005009820A1 (de) | 2005-03-01 | 2006-09-07 | Polyic Gmbh & Co. Kg | Elektronikbaugruppe mit organischen Logik-Schaltelementen |
| US8173630B2 (en) * | 2005-06-03 | 2012-05-08 | The Regents Of The University Of California | Multipodal tethers for high-density attachment of redox-active moieties to substrates |
| US8062756B2 (en) | 2005-08-26 | 2011-11-22 | The Regents oft the University of California | Stepwise growth of oligomeric redox-active molecules on a surface without the use of protecting groups |
| US7642546B2 (en) * | 2005-12-01 | 2010-01-05 | Zettacore, Inc. | Molecular memory devices including solid-state dielectric layers and related methods |
| KR101249117B1 (ko) * | 2006-11-13 | 2013-03-29 | 삼성전자주식회사 | 메탈로센 덴드리머, 이를 이용한 유기 메모리 소자 및 그의제조방법 |
| TW200906895A (en) * | 2007-05-21 | 2009-02-16 | Plextronics Inc | Porphyrin and conductive polymer compositions for use in solid-state electronic devices |
| DE102007028236A1 (de) | 2007-06-20 | 2009-01-02 | Siemens Ag | Halbleitendes Material und organische Gleichrichterdiode |
| JP2010538160A (ja) * | 2007-08-31 | 2010-12-09 | ゼタコア インコーポレイテッド | 興味ある分子の結合を促進するための表面処理方法、該方法により形成されたコーティングおよび装置 |
| US20090056994A1 (en) * | 2007-08-31 | 2009-03-05 | Kuhr Werner G | Methods of Treating a Surface to Promote Metal Plating and Devices Formed |
| US20090225585A1 (en) * | 2007-12-27 | 2009-09-10 | Hawkins J Adrian | Self-Contained Charge Storage Molecules for Use in Molecular Capacitors |
| GR20080100269A (el) * | 2008-04-18 | 2009-11-19 | ������ ������� ������� ��������� (�����) "����������" | Διαταξεις μνημης με χρηση πολυμερικων υλικων που ειναι αγωγοι πρωτονιων |
| US8927775B2 (en) | 2008-07-14 | 2015-01-06 | Esionic Es, Inc. | Phosphonium ionic liquids, salts, compositions, methods of making and devices formed there from |
| US8907133B2 (en) | 2008-07-14 | 2014-12-09 | Esionic Es, Inc. | Electrolyte compositions and electrochemical double layer capacitors formed there from |
| US8525155B2 (en) | 2008-07-14 | 2013-09-03 | Esionic Es, Inc. | Phosphonium ionic liquids, compositions, methods of making and electronic devices formed there from |
| US8319208B2 (en) | 2008-10-02 | 2012-11-27 | Zettacore Ip, Inc. | Methods of forming thin films for molecular based devices |
| JP5444747B2 (ja) * | 2009-02-17 | 2014-03-19 | ソニー株式会社 | カラー撮像素子およびその製造方法ならびに光センサーおよびその製造方法ならびに光電変換素子およびその製造方法ならびに電子機器 |
| FR2951028B1 (fr) * | 2009-10-05 | 2012-08-03 | Commissariat Energie Atomique | Memoire organique a double grille et procede de realisation |
| US8289830B2 (en) * | 2009-12-16 | 2012-10-16 | International Business Machines Corporation | Storing data on fiber data storage media |
| WO2011141913A1 (en) * | 2010-05-11 | 2011-11-17 | Yeda Research And Development Co. Ltd | Solid, multi-state molecular random access memory (ram) |
| WO2012005723A1 (en) | 2010-07-06 | 2012-01-12 | Zettacore, Inc. | Methods of treating copper surfaces for enhancing adhesion to organic substrates for use in printed circuit boards |
| CN103118806B (zh) | 2010-07-06 | 2016-10-12 | 埃托特克德国有限公司 | 处理金属表面的方法和由此形成的器件 |
| US9028722B2 (en) * | 2010-10-29 | 2015-05-12 | Centre National De La Recherche Scientifique (C.N.R.S.) | Electric conduction through supramolecular assemblies of triarylamines |
| CN102391270A (zh) * | 2011-10-17 | 2012-03-28 | 华东理工大学 | 四-(邻新戊酰胺基苯基)卟啉锌异构体化合物的制备方法 |
| EP2870644A2 (en) | 2012-07-09 | 2015-05-13 | Yeda Research and Development Co. Ltd. | Logic circuits with plug and play solid-state molecular chips |
| JP6158013B2 (ja) * | 2013-09-24 | 2017-07-05 | 株式会社東芝 | 有機分子メモリ |
| IL229525A0 (en) | 2013-11-20 | 2014-01-30 | Yeda Res & Dev | Metal complexes of tris-bipyridyl and their uses in electrochromic applications |
| CN107093750A (zh) * | 2017-04-27 | 2017-08-25 | 高延敏 | 一种组合物及其用途以及锌锰电池 |
| CN111943281B (zh) * | 2020-08-04 | 2022-05-24 | 厦门厦钨新能源材料股份有限公司 | 一种环境友好型前驱体和复合氧化物粉体及其制备方法和应用 |
Family Cites Families (60)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3637581A (en) | 1967-08-04 | 1972-01-25 | Shojiro Horiguchi | Method of making chromogen-bonded-polymer and products thereof |
| US3833894A (en) | 1973-06-20 | 1974-09-03 | Ibm | Organic memory device |
| US4618509A (en) | 1981-03-23 | 1986-10-21 | University Of Delaware | Arrays of stacked metal coordination compounds |
| US4499260A (en) * | 1982-11-10 | 1985-02-12 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Phthalocyanine polymers |
| GB8409022D0 (en) | 1984-04-06 | 1984-05-16 | Qmc Ind Res | Information holding device |
| US4663270A (en) | 1984-04-25 | 1987-05-05 | The Johns Hopkins University | Multistate optical switching and memory using an amphoteric organic charge transfer material |
| US4717673A (en) * | 1984-11-23 | 1988-01-05 | Massachusetts Institute Of Technology | Microelectrochemical devices |
| US4728724A (en) | 1985-04-08 | 1988-03-01 | Hoechst Celanese Corporation | Optical data storage medium comprising a chromophore/polymer information layer |
| GB8517622D0 (en) | 1985-07-12 | 1985-08-21 | Secr Defence | Electrically conducting conjugated polymers |
| EP0272935B1 (en) | 1986-12-24 | 1994-03-16 | Canon Kabushiki Kaisha | Recording device and reproducing device |
| JPS63237293A (ja) | 1987-03-24 | 1988-10-03 | Matsushita Electric Ind Co Ltd | 可変調分子素子 |
| EP0307211A3 (en) | 1987-09-10 | 1991-05-15 | Seiko Instruments Inc. | Memory reading device |
| EP0307210A3 (en) | 1987-09-10 | 1991-05-15 | Seiko Instruments Inc. | Memory writing apparatus |
| US5075738A (en) | 1988-03-28 | 1991-12-24 | Canon Kabushiki Kaisha | Switching device and method of preparing it |
| US5463014A (en) | 1988-05-13 | 1995-10-31 | The Ohio State University Research Foundation | Electromagnetic radiation absorbers and modulators comprising polyaniline |
| US5280183A (en) | 1988-05-31 | 1994-01-18 | Edison Polymer Innovation Corporation | Microelectronic device employing multiring phthalocyanine compound |
| US5063417A (en) | 1988-07-18 | 1991-11-05 | California Institute Of Technology | Molecular shift register based on electron transfer |
| JPH0260166A (ja) * | 1988-08-26 | 1990-02-28 | Nippon Telegr & Teleph Corp <Ntt> | フルバレン類薄膜を用いたメモリー素子 |
| US5091502A (en) | 1988-09-23 | 1992-02-25 | General Petrochemical Industries Ltd | Tetraketone porphyrin monomers and the porphyrin-based polymers thereof |
| CA2000071C (en) | 1988-10-04 | 1997-01-28 | Haruki Kawada | Recording and reproducing apparatus and recording and reproducing method and recording medium for the recording and reproducing method |
| US5135637A (en) * | 1989-03-24 | 1992-08-04 | Idemitsu Kosan Co., Ltd. | Eerrocene derivatives, surfactants containing same and process for producing organic thin films |
| US5010451A (en) * | 1989-03-29 | 1991-04-23 | Mitsubishi Denki K.K. | Electronic device |
| JP2806963B2 (ja) * | 1989-03-29 | 1998-09-30 | 三菱電機株式会社 | 光スイッチ素子 |
| US5135537A (en) | 1989-05-11 | 1992-08-04 | Lamb Mark A | Home traction device |
| US5264876A (en) | 1989-08-10 | 1993-11-23 | Canon Kabushiki Kaisha | Recording medium, method for preparing the same, recording and reproducing device, and recording, reproducing and erasing method by use of such recording medium |
| US5016063A (en) | 1989-08-14 | 1991-05-14 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Molecular implementation of molecular shift register memories |
| EP0416882B1 (en) | 1989-09-07 | 1997-03-05 | Canon Kabushiki Kaisha | Information storage, accessing and processing |
| JPH0444362A (ja) | 1990-06-12 | 1992-02-14 | Nec Corp | 有機量子半導体及び量子半導体素子 |
| JP2778304B2 (ja) * | 1991-09-17 | 1998-07-23 | 三菱電機株式会社 | 有機電子素子材料 |
| JP3437195B2 (ja) | 1991-10-01 | 2003-08-18 | キヤノン株式会社 | Mim型電気素子とその製造方法、及びこれを用いた画像表示装置、描画装置 |
| JPH07501845A (ja) | 1991-12-13 | 1995-02-23 | エクソン・ケミカル・パテンツ・インク | エチレンとより長いアルファーオレフィンのコポリマー |
| JP2888639B2 (ja) | 1992-04-20 | 1999-05-10 | エクソン・ケミカル・パテンツ・インク | エチレン/分枝鎖オレフィンのコポリマー |
| US5744598A (en) | 1992-06-19 | 1998-04-28 | University Of Toledo | Imines of porphyrins, of porphyrin derivatives, and of related compounds, and pharmaceutical compositions containing such imines |
| US5434842A (en) | 1992-07-17 | 1995-07-18 | Biotechnology Research And Development Corporation | Reading and writing stored information by means of electrochemistry |
| US5327373A (en) | 1992-08-21 | 1994-07-05 | Board Of Regents, The University Of Texas System | Optoelectronic memories with photoconductive thin films |
| EP0591595A1 (en) | 1992-10-08 | 1994-04-13 | International Business Machines Corporation | Molecular recording/reproducing method and recording medium |
| US5312896A (en) | 1992-10-09 | 1994-05-17 | Sri International | Metal ion porphyrin-containing poly(imide) |
| US5252698A (en) | 1992-10-09 | 1993-10-12 | Sri International | Metal ion porphyrin-containing poly(azine) |
| US5539100A (en) | 1993-07-01 | 1996-07-23 | The United States Of America As Represented By The United States Department Of Energy | Organic solid state switches incorporating porphyrin compounds and method for producing organic solid state optical switches |
| US5506420A (en) | 1994-09-14 | 1996-04-09 | The Regents Of The University Of California | Semiconductor bio-electronic devices incorporating biochemical stabilization layers |
| US5541807A (en) | 1995-03-17 | 1996-07-30 | Evans, Jr.; Joseph T. | Ferroelectric based capacitor for use in memory systems and method for fabricating the same |
| US5814420A (en) | 1994-11-23 | 1998-09-29 | Polyplus Battery Company, Inc. | Rechargeable positive electrodes |
| JP2728123B2 (ja) * | 1995-07-24 | 1998-03-18 | 日本電気株式会社 | スイッチング素子およびその製造方法 |
| US5840443A (en) | 1995-07-31 | 1998-11-24 | Midwest Research Institute | Redox polymer electrodes for advanced batteries |
| US5858666A (en) | 1996-08-29 | 1999-01-12 | Biotechnology Research And Development Corporation | Apparatus and method of detection employing an AC frequency sensor array |
| US6031756A (en) | 1997-02-06 | 2000-02-29 | International Business Machines Corporation | Molecule, layered medium and method for creating a pattern |
| US6013459A (en) | 1997-06-12 | 2000-01-11 | Clinical Micro Sensors, Inc. | Detection of analytes using reorganization energy |
| JP3761300B2 (ja) * | 1997-09-30 | 2006-03-29 | 株式会社東芝 | シフトレジスター型記憶素子 |
| EP1036129A4 (en) | 1997-11-07 | 2000-12-27 | Omd Devices Llc | FLUORESCENCE COMPOSITION FOR THE PRODUCTION OF OPTICAL STORAGE DISKS |
| US6034251A (en) | 1997-11-07 | 2000-03-07 | Schering Corporation | Phenyl-alkyl-imidazoles |
| US6097627A (en) * | 1998-09-30 | 2000-08-01 | Motorola, Inc. | Quantum random address memory with nano-diode mixer |
| US6518156B1 (en) * | 1999-03-29 | 2003-02-11 | Hewlett-Packard Company | Configurable nanoscale crossbar electronic circuits made by electrochemical reaction |
| US6128214A (en) | 1999-03-29 | 2000-10-03 | Hewlett-Packard | Molecular wire crossbar memory |
| US6324091B1 (en) | 2000-01-14 | 2001-11-27 | The Regents Of The University Of California | Tightly coupled porphyrin macrocycles for molecular memory storage |
| US6381169B1 (en) * | 1999-07-01 | 2002-04-30 | The Regents Of The University Of California | High density non-volatile memory device |
| EP1210714A4 (en) | 1999-07-01 | 2006-01-04 | Univ | HIGH DENSITY REMANENT MEMORY DEVICE |
| US6208553B1 (en) | 1999-07-01 | 2001-03-27 | The Regents Of The University Of California | High density non-volatile memory device incorporating thiol-derivatized porphyrins |
| US6272038B1 (en) | 2000-01-14 | 2001-08-07 | North Carolina State University | High-density non-volatile memory devices incorporating thiol-derivatized porphyrin trimers |
| US6212093B1 (en) | 2000-01-14 | 2001-04-03 | North Carolina State University | High-density non-volatile memory devices incorporating sandwich coordination compounds |
| US6728129B2 (en) * | 2002-02-19 | 2004-04-27 | The Regents Of The University Of California | Multistate triple-decker dyads in three distinct architectures for information storage applications |
-
2000
- 2000-06-28 EP EP00955240A patent/EP1210714A4/en not_active Withdrawn
- 2000-06-28 JP JP2001508444A patent/JP2003504839A/ja active Pending
- 2000-06-28 IL IL14711900A patent/IL147119A0/xx active IP Right Grant
- 2000-06-28 WO PCT/US2000/017847 patent/WO2001003126A2/en not_active Ceased
- 2000-06-28 CA CA2377671A patent/CA2377671C/en not_active Expired - Fee Related
- 2000-06-28 AU AU67469/00A patent/AU764750B2/en not_active Ceased
- 2000-06-28 US US10/019,377 patent/US7042755B1/en not_active Expired - Fee Related
-
2001
- 2001-12-16 IL IL147119A patent/IL147119A/en not_active IP Right Cessation
- 2001-12-28 NO NO20016420A patent/NO20016420L/no not_active Application Discontinuation
-
2005
- 2005-11-03 US US11/266,776 patent/US7518905B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US20060209587A1 (en) | 2006-09-21 |
| NO20016420D0 (no) | 2001-12-28 |
| AU764750B2 (en) | 2003-08-28 |
| US7042755B1 (en) | 2006-05-09 |
| CA2377671A1 (en) | 2001-01-11 |
| WO2001003126A9 (en) | 2002-08-01 |
| JP2003504839A (ja) | 2003-02-04 |
| NO20016420L (no) | 2002-02-28 |
| WO2001003126A2 (en) | 2001-01-11 |
| WO2001003126A3 (en) | 2001-10-11 |
| AU6746900A (en) | 2001-01-22 |
| EP1210714A4 (en) | 2006-01-04 |
| IL147119A (en) | 2006-09-05 |
| US7518905B2 (en) | 2009-04-14 |
| EP1210714A2 (en) | 2002-06-05 |
| IL147119A0 (en) | 2002-08-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2377671C (en) | High density non-volatile memory device | |
| US6208553B1 (en) | High density non-volatile memory device incorporating thiol-derivatized porphyrins | |
| US6657884B2 (en) | High density non-volatile memory device | |
| US6212093B1 (en) | High-density non-volatile memory devices incorporating sandwich coordination compounds | |
| US6777516B2 (en) | Substrates carrying polymers of linked sandwich coordination compounds and methods of use thereof | |
| US6324091B1 (en) | Tightly coupled porphyrin macrocycles for molecular memory storage | |
| US6272038B1 (en) | High-density non-volatile memory devices incorporating thiol-derivatized porphyrin trimers | |
| US6728129B2 (en) | Multistate triple-decker dyads in three distinct architectures for information storage applications | |
| US6674121B2 (en) | Method and system for molecular charge storage field effect transistor | |
| US8173630B2 (en) | Multipodal tethers for high-density attachment of redox-active moieties to substrates | |
| US20050162895A1 (en) | Molecular memory arrays and devices | |
| US20060092687A1 (en) | Molecular memory devices and methods | |
| Erickson et al. | Tuning Electron-Transfer Properties in 5, 10, 15, 20-Tetra (1′-hexanoylferrocenyl) porphyrins as Prospective Systems for Quantum Cellular Automata and Platforms for Four-Bit Information Storage | |
| Nguyen et al. | Volatile conductance switching in molecular device based on viologen building block | |
| AU2004214622A1 (en) | Substrates carrying polymers of linked sandwich coordination compounds and methods of use thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20150629 |