KR20210148278A - 개선된 광 안정성 및 용해도를 갖는 광 변색성 및 전기 변색성 다이아릴에텐 화합물 - Google Patents
개선된 광 안정성 및 용해도를 갖는 광 변색성 및 전기 변색성 다이아릴에텐 화합물 Download PDFInfo
- Publication number
- KR20210148278A KR20210148278A KR1020217035733A KR20217035733A KR20210148278A KR 20210148278 A KR20210148278 A KR 20210148278A KR 1020217035733 A KR1020217035733 A KR 1020217035733A KR 20217035733 A KR20217035733 A KR 20217035733A KR 20210148278 A KR20210148278 A KR 20210148278A
- Authority
- KR
- South Korea
- Prior art keywords
- substituted
- saturated
- carbons
- branched
- unsaturated
- 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.)
- Ceased
Links
- -1 diarylethene compounds Chemical class 0.000 title claims abstract description 36
- 150000001875 compounds Chemical class 0.000 claims abstract description 66
- 229920006395 saturated elastomer Polymers 0.000 claims description 190
- 125000000217 alkyl group Chemical group 0.000 claims description 110
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 97
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 93
- 229910052757 nitrogen Inorganic materials 0.000 claims description 91
- 229910052760 oxygen Inorganic materials 0.000 claims description 90
- 229910052717 sulfur Inorganic materials 0.000 claims description 87
- 229910052710 silicon Inorganic materials 0.000 claims description 85
- 238000000034 method Methods 0.000 claims description 63
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 41
- KXSFECAJUBPPFE-UHFFFAOYSA-N 2,2':5',2''-terthiophene Chemical compound C1=CSC(C=2SC(=CC=2)C=2SC=CC=2)=C1 KXSFECAJUBPPFE-UHFFFAOYSA-N 0.000 claims description 33
- 239000002904 solvent Substances 0.000 claims description 33
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 29
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 28
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 28
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 25
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 18
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical group CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 claims description 16
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 15
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 15
- FGBHDLKMGUOJBA-UHFFFAOYSA-N 3-bromo-2,5-dithiophen-2-ylthiophene Chemical group BrC=1C=C(C=2SC=CC=2)SC=1C1=CC=CS1 FGBHDLKMGUOJBA-UHFFFAOYSA-N 0.000 claims description 13
- 239000002841 Lewis acid Substances 0.000 claims description 12
- 150000007517 lewis acids Chemical class 0.000 claims description 12
- 229930192474 thiophene Natural products 0.000 claims description 12
- 239000012039 electrophile Substances 0.000 claims description 11
- 239000000758 substrate Substances 0.000 claims description 11
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 10
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 claims description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 5
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 claims description 4
- 230000002194 synthesizing effect Effects 0.000 claims description 4
- RKSOPLXZQNSWAS-UHFFFAOYSA-N tert-butyl bromide Chemical compound CC(C)(C)Br RKSOPLXZQNSWAS-UHFFFAOYSA-N 0.000 claims description 4
- 229920000123 polythiophene Polymers 0.000 claims description 3
- 150000003577 thiophenes Chemical class 0.000 claims description 3
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 2
- 239000012346 acetyl chloride Substances 0.000 claims description 2
- 230000010933 acylation Effects 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- CECABOMBVQNBEC-UHFFFAOYSA-K aluminium iodide Chemical compound I[Al](I)I CECABOMBVQNBEC-UHFFFAOYSA-K 0.000 claims description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 2
- 150000004820 halides Chemical group 0.000 claims description 2
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 claims description 2
- GYCHYNMREWYSKH-UHFFFAOYSA-L iron(ii) bromide Chemical compound [Fe+2].[Br-].[Br-] GYCHYNMREWYSKH-UHFFFAOYSA-L 0.000 claims description 2
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims 2
- 239000011574 phosphorus Substances 0.000 claims 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 150000003949 imides Chemical class 0.000 claims 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract description 19
- 230000003287 optical effect Effects 0.000 abstract description 13
- 230000004048 modification Effects 0.000 abstract description 4
- 238000012986 modification Methods 0.000 abstract description 4
- 238000010348 incorporation Methods 0.000 abstract description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 138
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 134
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 98
- 239000000243 solution Substances 0.000 description 71
- 239000000047 product Substances 0.000 description 60
- 239000000203 mixture Substances 0.000 description 59
- 239000000463 material Substances 0.000 description 48
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 47
- 238000002360 preparation method Methods 0.000 description 37
- 239000003480 eluent Substances 0.000 description 33
- 235000019439 ethyl acetate Nutrition 0.000 description 33
- 239000011541 reaction mixture Substances 0.000 description 32
- 238000005481 NMR spectroscopy Methods 0.000 description 29
- 238000001816 cooling Methods 0.000 description 29
- 238000004440 column chromatography Methods 0.000 description 27
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 26
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 24
- 230000003647 oxidation Effects 0.000 description 24
- 238000007254 oxidation reaction Methods 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 21
- 239000007787 solid Substances 0.000 description 21
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 238000010992 reflux Methods 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 15
- 238000002835 absorbance Methods 0.000 description 14
- 238000000354 decomposition reaction Methods 0.000 description 13
- 241000894007 species Species 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- 125000001424 substituent group Chemical group 0.000 description 13
- 239000000284 extract Substances 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 12
- 235000019341 magnesium sulphate Nutrition 0.000 description 12
- 239000012071 phase Substances 0.000 description 12
- 238000010791 quenching Methods 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 11
- 125000004122 cyclic group Chemical group 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- 238000000746 purification Methods 0.000 description 10
- 238000006798 ring closing metathesis reaction Methods 0.000 description 10
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 10
- 239000013058 crude material Substances 0.000 description 9
- 239000007857 degradation product Substances 0.000 description 9
- 230000000171 quenching effect Effects 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 230000000903 blocking effect Effects 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 238000013459 approach Methods 0.000 description 7
- 230000015556 catabolic process Effects 0.000 description 7
- 238000006731 degradation reaction Methods 0.000 description 7
- 229960004132 diethyl ether Drugs 0.000 description 7
- 238000003818 flash chromatography Methods 0.000 description 7
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 7
- 238000007142 ring opening reaction Methods 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- 230000007704 transition Effects 0.000 description 7
- KEDFYIVPXZVKFM-UHFFFAOYSA-N 1-benzofuran-5,6-diol Chemical compound C1=C(O)C(O)=CC2=C1OC=C2 KEDFYIVPXZVKFM-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- 238000006467 substitution reaction Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 238000002834 transmittance Methods 0.000 description 6
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 5
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 230000005540 biological transmission Effects 0.000 description 5
- ZWKKRUNHAVNSFW-UHFFFAOYSA-N dimethyl 2-methylpentanedioate Chemical compound COC(=O)CCC(C)C(=O)OC ZWKKRUNHAVNSFW-UHFFFAOYSA-N 0.000 description 5
- XBPOBCXHALHJFP-UHFFFAOYSA-N ethyl 4-bromobutanoate Chemical compound CCOC(=O)CCCBr XBPOBCXHALHJFP-UHFFFAOYSA-N 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 150000005839 radical cations Chemical class 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 5
- 235000019345 sodium thiosulphate Nutrition 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 230000007246 mechanism Effects 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 239000012047 saturated solution Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 229910052724 xenon Inorganic materials 0.000 description 4
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 238000006349 photocyclization reaction Methods 0.000 description 3
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 230000003381 solubilizing effect Effects 0.000 description 3
- DAFHKNAQFPVRKR-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylpropanoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)C DAFHKNAQFPVRKR-UHFFFAOYSA-N 0.000 description 2
- YBMDPYAEZDJWNY-UHFFFAOYSA-N 1,2,3,3,4,4,5,5-octafluorocyclopentene Chemical compound FC1=C(F)C(F)(F)C(F)(F)C1(F)F YBMDPYAEZDJWNY-UHFFFAOYSA-N 0.000 description 2
- IZFOPMSVNDORMZ-UHFFFAOYSA-N 1-benzofuran-5-ol Chemical compound OC1=CC=C2OC=CC2=C1 IZFOPMSVNDORMZ-UHFFFAOYSA-N 0.000 description 2
- UWNADWZGEHDQAB-UHFFFAOYSA-N 2,5-dimethylhexane Chemical compound CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 2
- COBPKKZHLDDMTB-UHFFFAOYSA-N 2-[2-(2-butoxyethoxy)ethoxy]ethanol Chemical compound CCCCOCCOCCOCCO COBPKKZHLDDMTB-UHFFFAOYSA-N 0.000 description 2
- WFSMVVDJSNMRAR-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]ethanol Chemical compound CCOCCOCCOCCO WFSMVVDJSNMRAR-UHFFFAOYSA-N 0.000 description 2
- YYJBWYBULYUKMR-UHFFFAOYSA-N 2-bromo-3-methylthiophene Chemical compound CC=1C=CSC=1Br YYJBWYBULYUKMR-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XJHGWLCPWGQAKQ-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C=1OC2=C(C=1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC(=C1)C=1SC(=CC=1)C(C)(C)C)C=1SC(=CC=1)C(C)(C)C)C=C(C(=C2)OCCOC)OCCOC Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C=1OC2=C(C=1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC(=C1)C=1SC(=CC=1)C(C)(C)C)C=1SC(=CC=1)C(C)(C)C)C=C(C(=C2)OCCOC)OCCOC XJHGWLCPWGQAKQ-UHFFFAOYSA-N 0.000 description 2
- DRBGBMKEWRQENQ-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C=1OC2=C(C=1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC(=C1)C=1SC(=CC=1)C(C)(C)C)C=1SC(=CC=1)C(C)(C)C)C=C(C=C2)OC Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C=1OC2=C(C=1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC(=C1)C=1SC(=CC=1)C(C)(C)C)C=1SC(=CC=1)C(C)(C)C)C=C(C=C2)OC DRBGBMKEWRQENQ-UHFFFAOYSA-N 0.000 description 2
- MXKJSYURBYFGKG-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C=1OC2=C(C=1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC(=C1)C=1SC(=CC=1)C(C)(C)C)C=1SC=C(C=1)C(C)(C)C)C=C(C(=C2)OCCCOC)OCCCOC Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C=1OC2=C(C=1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC(=C1)C=1SC(=CC=1)C(C)(C)C)C=1SC=C(C=1)C(C)(C)C)C=C(C(=C2)OCCCOC)OCCCOC MXKJSYURBYFGKG-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000003547 Friedel-Crafts alkylation reaction Methods 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- FLIACVVOZYBSBS-UHFFFAOYSA-N Methyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC FLIACVVOZYBSBS-UHFFFAOYSA-N 0.000 description 2
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 238000012356 Product development Methods 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- UYXTWWCETRIEDR-UHFFFAOYSA-N Tributyrin Chemical compound CCCC(=O)OCC(OC(=O)CCC)COC(=O)CCC UYXTWWCETRIEDR-UHFFFAOYSA-N 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000013065 commercial product Substances 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- XTDYIOOONNVFMA-UHFFFAOYSA-N dimethyl pentanedioate Chemical compound COC(=O)CCCC(=O)OC XTDYIOOONNVFMA-UHFFFAOYSA-N 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 229940052303 ethers for general anesthesia Drugs 0.000 description 2
- 239000005329 float glass Substances 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- NCDCLPBOMHPFCV-UHFFFAOYSA-N hexyl hexanoate Chemical compound CCCCCCOC(=O)CCCCC NCDCLPBOMHPFCV-UHFFFAOYSA-N 0.000 description 2
- PBGWNXWNCSSXCO-UHFFFAOYSA-N hexyl octanoate Chemical compound CCCCCCCC(=O)OCCCCCC PBGWNXWNCSSXCO-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 230000002427 irreversible effect Effects 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 2
- FTSXVYQZLNPTCM-UHFFFAOYSA-N (3-benzoyloxy-2,2,4-trimethylpentyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC(C)(C)C(C(C)C)OC(=O)C1=CC=CC=C1 FTSXVYQZLNPTCM-UHFFFAOYSA-N 0.000 description 1
- HBXRPXYBMZDIQL-UHFFFAOYSA-N 1$l^{2}-borolane Chemical compound [B]1CCCC1 HBXRPXYBMZDIQL-UHFFFAOYSA-N 0.000 description 1
- NKJOXAZJBOMXID-UHFFFAOYSA-N 1,1'-Oxybisoctane Chemical compound CCCCCCCCOCCCCCCCC NKJOXAZJBOMXID-UHFFFAOYSA-N 0.000 description 1
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- ZZXUZKXVROWEIF-UHFFFAOYSA-N 1,2-butylene carbonate Chemical compound CCC1COC(=O)O1 ZZXUZKXVROWEIF-UHFFFAOYSA-N 0.000 description 1
- UPNNXUSUOSTIIM-UHFFFAOYSA-N 1,2-dithietane Chemical compound C1CSS1 UPNNXUSUOSTIIM-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
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- IMLSAISZLJGWPP-UHFFFAOYSA-N 1,3-dithiolane Chemical compound C1CSCS1 IMLSAISZLJGWPP-UHFFFAOYSA-N 0.000 description 1
- HPFDGTFXAVIVTH-UHFFFAOYSA-N 1-((1-((1-Methoxypropan-2-yl)oxy)propan-2-yl)oxy)propan-2-ol Chemical compound COCC(C)OCC(C)OCC(C)O HPFDGTFXAVIVTH-UHFFFAOYSA-N 0.000 description 1
- 239000005968 1-Decanol Substances 0.000 description 1
- KZVBBTZJMSWGTK-UHFFFAOYSA-N 1-[2-(2-butoxyethoxy)ethoxy]butane Chemical compound CCCCOCCOCCOCCCC KZVBBTZJMSWGTK-UHFFFAOYSA-N 0.000 description 1
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
- CEVMYGZHEJSOHZ-UHFFFAOYSA-N 1-bromo-3-methoxypropane Chemical compound COCCCBr CEVMYGZHEJSOHZ-UHFFFAOYSA-N 0.000 description 1
- LOWMYOWHQMKBTM-UHFFFAOYSA-N 1-butylsulfinylbutane Chemical compound CCCCS(=O)CCCC LOWMYOWHQMKBTM-UHFFFAOYSA-N 0.000 description 1
- TVBIUBUAMWKXDX-UHFFFAOYSA-N 1-chloro-2,4-dimethylpentane Chemical compound CC(C)CC(C)CCl TVBIUBUAMWKXDX-UHFFFAOYSA-N 0.000 description 1
- GQOXGLGIJBSUPF-UHFFFAOYSA-N 1-chloro-2,6-dimethylheptane Chemical compound CC(C)CCCC(C)CCl GQOXGLGIJBSUPF-UHFFFAOYSA-N 0.000 description 1
- IBLKWZIFZMJLFL-UHFFFAOYSA-N 1-phenoxypropan-2-ol Chemical compound CC(O)COC1=CC=CC=C1 IBLKWZIFZMJLFL-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- ZHKJHQBOAJQXQR-UHFFFAOYSA-N 1H-azirine Chemical compound N1C=C1 ZHKJHQBOAJQXQR-UHFFFAOYSA-N 0.000 description 1
- SKDNDSLDRLEELJ-UHFFFAOYSA-N 2,3,5-tribromothiophene Chemical compound BrC1=CC(Br)=C(Br)S1 SKDNDSLDRLEELJ-UHFFFAOYSA-N 0.000 description 1
- WCVOGSZTONGSQY-UHFFFAOYSA-N 2,4,6-trichloroanisole Chemical compound COC1=C(Cl)C=C(Cl)C=C1Cl WCVOGSZTONGSQY-UHFFFAOYSA-N 0.000 description 1
- LHJHUCCRNCKRQN-UHFFFAOYSA-N 2,4-dichloro-2,4-dimethylpentane Chemical compound CC(C)(Cl)CC(C)(C)Cl LHJHUCCRNCKRQN-UHFFFAOYSA-N 0.000 description 1
- DBTGFWMBFZBBEF-UHFFFAOYSA-N 2,4-dimethylpentane-2,4-diol Chemical compound CC(C)(O)CC(C)(C)O DBTGFWMBFZBBEF-UHFFFAOYSA-N 0.000 description 1
- HSTAGCWQAIXJQM-UHFFFAOYSA-N 2,5-dichloro-2,5-dimethylhexane Chemical compound CC(C)(Cl)CCC(C)(C)Cl HSTAGCWQAIXJQM-UHFFFAOYSA-N 0.000 description 1
- JDFNLGAISOXLHH-UHFFFAOYSA-N 2,6-dichloro-2,6-dimethylheptane Chemical compound CC(C)(Cl)CCCC(C)(C)Cl JDFNLGAISOXLHH-UHFFFAOYSA-N 0.000 description 1
- PREYRMMHKDIKLF-UHFFFAOYSA-N 2,6-dimethylheptane-2,6-diol Chemical compound CC(C)(O)CCCC(C)(C)O PREYRMMHKDIKLF-UHFFFAOYSA-N 0.000 description 1
- GHVNZKHFRXPRKS-UHFFFAOYSA-N 2-(2,5-dioxopyrrolidin-1-yl)ethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCCN1C(=O)CCC1=O GHVNZKHFRXPRKS-UHFFFAOYSA-N 0.000 description 1
- VXQBJTKSVGFQOL-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethyl acetate Chemical compound CCCCOCCOCCOC(C)=O VXQBJTKSVGFQOL-UHFFFAOYSA-N 0.000 description 1
- WMDZKDKPYCNCDZ-UHFFFAOYSA-N 2-(2-butoxypropoxy)propan-1-ol Chemical compound CCCCOC(C)COC(C)CO WMDZKDKPYCNCDZ-UHFFFAOYSA-N 0.000 description 1
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 1
- GZMAAYIALGURDQ-UHFFFAOYSA-N 2-(2-hexoxyethoxy)ethanol Chemical compound CCCCCCOCCOCCO GZMAAYIALGURDQ-UHFFFAOYSA-N 0.000 description 1
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 description 1
- KBVHXYDAYZDUML-UHFFFAOYSA-N 2-(2-oxo-1,3-oxazolidin-3-yl)ethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCCN1C(=O)OCC1 KBVHXYDAYZDUML-UHFFFAOYSA-N 0.000 description 1
- RVHDHORNHZZYDR-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-3-(2,3,3,4,4,5,5-heptafluorocyclopenten-1-yl)-5,6-dimethoxy-1-benzofuran Chemical compound C1=2C=C(OC)C(OC)=CC=2OC(C=2C=CC(=CC=2)C(C)(C)C)=C1C1=C(F)C(F)(F)C(F)(F)C1(F)F RVHDHORNHZZYDR-UHFFFAOYSA-N 0.000 description 1
- QUGJZLUVNVZSKX-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-3-[2-(2,5-dithiophen-2-ylthiophen-3-yl)-3,3,4,4,5,5-hexafluorocyclopenten-1-yl]-5,6-dimethoxy-1-benzofuran Chemical compound C1=2C=C(OC)C(OC)=CC=2OC(C=2C=CC(=CC=2)C(C)(C)C)=C1C(C(C(F)(F)C1(F)F)(F)F)=C1C=1C=C(C=2SC=CC=2)SC=1C1=CC=CS1 QUGJZLUVNVZSKX-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 1
- GYSSYGOYECOPGB-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]ethyl 4-methylbenzenesulfonate Chemical compound CCOCCOCCOCCOS(=O)(=O)C1=CC=C(C)C=C1 GYSSYGOYECOPGB-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- JEYLQCXBYFQJRO-UHFFFAOYSA-N 2-[2-[2-(2-ethylbutanoyloxy)ethoxy]ethoxy]ethyl 2-ethylbutanoate Chemical compound CCC(CC)C(=O)OCCOCCOCCOC(=O)C(CC)CC JEYLQCXBYFQJRO-UHFFFAOYSA-N 0.000 description 1
- FECDACOUYKFOOP-RGURZIINSA-N 2-ethylhexyl (2s)-2-hydroxypropanoate Chemical compound CCCCC(CC)COC(=O)[C@H](C)O FECDACOUYKFOOP-RGURZIINSA-N 0.000 description 1
- MUHFRORXWCGZGE-KTKRTIGZSA-N 2-hydroxyethyl (z)-octadec-9-enoate Polymers CCCCCCCC\C=C/CCCCCCCC(=O)OCCO MUHFRORXWCGZGE-KTKRTIGZSA-N 0.000 description 1
- FPPLREPCQJZDAQ-UHFFFAOYSA-N 2-methylpentanedinitrile Chemical compound N#CC(C)CCC#N FPPLREPCQJZDAQ-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- ALKCLFLTXBBMMP-UHFFFAOYSA-N 3,7-dimethylocta-1,6-dien-3-yl hexanoate Chemical compound CCCCCC(=O)OC(C)(C=C)CCC=C(C)C ALKCLFLTXBBMMP-UHFFFAOYSA-N 0.000 description 1
- QSSDFXGXUGCLSY-UHFFFAOYSA-N 3-[3-(3-butoxypropoxy)propoxy]propan-1-ol Chemical compound CCCCOCCCOCCCOCCCO QSSDFXGXUGCLSY-UHFFFAOYSA-N 0.000 description 1
- XYHGANYLLUGCSB-UHFFFAOYSA-N 3-bromo-2-(4-tert-butylphenyl)-6-methoxy-1-benzofuran Chemical compound O1C2=CC(OC)=CC=C2C(Br)=C1C1=CC=C(C(C)(C)C)C=C1 XYHGANYLLUGCSB-UHFFFAOYSA-N 0.000 description 1
- NUCFNMOPTGEHQA-UHFFFAOYSA-N 3-bromo-2h-pyrazolo[4,3-c]pyridine Chemical compound C1=NC=C2C(Br)=NNC2=C1 NUCFNMOPTGEHQA-UHFFFAOYSA-N 0.000 description 1
- HWZUQAKHJDKBOE-UHFFFAOYSA-N 3-methoxypropyl 4-methylbenzenesulfonate Chemical compound COCCCOS(=O)(=O)C1=CC=C(C)C=C1 HWZUQAKHJDKBOE-UHFFFAOYSA-N 0.000 description 1
- VWIIJDNADIEEDB-UHFFFAOYSA-N 3-methyl-1,3-oxazolidin-2-one Chemical compound CN1CCOC1=O VWIIJDNADIEEDB-UHFFFAOYSA-N 0.000 description 1
- QKVUSSUOYHTOFQ-UHFFFAOYSA-N 3-methyl-n,n-bis(3-methylbutyl)butan-1-amine Chemical compound CC(C)CCN(CCC(C)C)CCC(C)C QKVUSSUOYHTOFQ-UHFFFAOYSA-N 0.000 description 1
- LWLOKSXSAUHTJO-UHFFFAOYSA-N 4,5-dimethyl-1,3-dioxolan-2-one Chemical compound CC1OC(=O)OC1C LWLOKSXSAUHTJO-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- UJUCBOIXAMPUQL-UHFFFAOYSA-N 7-aminothieno[2,3-b]pyrazine-6-carboxylic acid Chemical compound C1=CN=C2C(N)=C(C(O)=O)SC2=N1 UJUCBOIXAMPUQL-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- PLRDQNVJPFUJDI-UHFFFAOYSA-N BrC1=C(OC2=C1C=C(C=C2)OC)C1=CC=C(C=C1)C(C)(C)C Chemical compound BrC1=C(OC2=C1C=C(C=C2)OC)C1=CC=C(C=C1)C(C)(C)C PLRDQNVJPFUJDI-UHFFFAOYSA-N 0.000 description 1
- FDXJVJGLYMARFP-UHFFFAOYSA-N BrC1=C(SC(=C1)C1=CC2=C(S1)C(CC2(C)C)(C)C)C1=CC2=C(S1)C(CC2(C)C)(C)C Chemical compound BrC1=C(SC(=C1)C1=CC2=C(S1)C(CC2(C)C)(C)C)C1=CC2=C(S1)C(CC2(C)C)(C)C FDXJVJGLYMARFP-UHFFFAOYSA-N 0.000 description 1
- VTTDILJFDUDAKI-UHFFFAOYSA-N BrC1=C(SC(=C1)C1=CC2=C(S1)C(CCC2(C)C)(C)C)C1=CC2=C(S1)C(CCC2(C)C)(C)C Chemical compound BrC1=C(SC(=C1)C1=CC2=C(S1)C(CCC2(C)C)(C)C)C1=CC2=C(S1)C(CCC2(C)C)(C)C VTTDILJFDUDAKI-UHFFFAOYSA-N 0.000 description 1
- FXVUAXCAPOQBOI-UHFFFAOYSA-N BrC1=C(SC(=C1)C1=CC2=C(S1)C(CCCC2(C)C)(C)C)C1=CC2=C(S1)C(CCCC2(C)C)(C)C Chemical compound BrC1=C(SC(=C1)C1=CC2=C(S1)C(CCCC2(C)C)(C)C)C1=CC2=C(S1)C(CCCC2(C)C)(C)C FXVUAXCAPOQBOI-UHFFFAOYSA-N 0.000 description 1
- LUMMBIKFOQQFME-UHFFFAOYSA-N BrC=1C=C(SC=1Br)C=1SC(=CC=1)C(C)(C)C Chemical compound BrC=1C=C(SC=1Br)C=1SC(=CC=1)C(C)(C)C LUMMBIKFOQQFME-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- GFKPFOOHRLKECB-UHFFFAOYSA-N C(C)(=O)OC=1C(=CC2=C(C(=C(O2)C2=CC=C(C=C2)C(C)(C)C)C2=C(C(C(C2(F)F)(F)F)(F)F)C2=C(SC(=C2)C=2SC(=CC=2)C(C)(C)C)C=2SC(=CC=2)C(C)(C)C)C=1)OC(C)=O Chemical compound C(C)(=O)OC=1C(=CC2=C(C(=C(O2)C2=CC=C(C=C2)C(C)(C)C)C2=C(C(C(C2(F)F)(F)F)(F)F)C2=C(SC(=C2)C=2SC(=CC=2)C(C)(C)C)C=2SC(=CC=2)C(C)(C)C)C=1)OC(C)=O GFKPFOOHRLKECB-UHFFFAOYSA-N 0.000 description 1
- PQBPEHWHWUYFEC-UHFFFAOYSA-N C(C)(=O)OC=1C(=CC2=C(C(=C(O2)C2=CC=C(C=C2)C(C)(C)C)C2=C(C(C(C2(F)F)(F)F)(F)F)C2=C(SC(=C2)C=2SC=C(C=2)C(C)(C)C)C=2SC=C(C=2)C(C)(C)C)C=1)OC(C)=O Chemical compound C(C)(=O)OC=1C(=CC2=C(C(=C(O2)C2=CC=C(C=C2)C(C)(C)C)C2=C(C(C(C2(F)F)(F)F)(F)F)C2=C(SC(=C2)C=2SC=C(C=2)C(C)(C)C)C=2SC=C(C=2)C(C)(C)C)C=1)OC(C)=O PQBPEHWHWUYFEC-UHFFFAOYSA-N 0.000 description 1
- WWNJKHIWNPGQNB-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C=1OC2=C(C=1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC(=C1)C=1SC(=CC=1)C(C)(C)C)C=1SC(=CC=1)C(C)(C)C)C=C(C(=C2)O)O Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C=1OC2=C(C=1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC(=C1)C=1SC(=CC=1)C(C)(C)C)C=1SC(=CC=1)C(C)(C)C)C=C(C(=C2)O)O WWNJKHIWNPGQNB-UHFFFAOYSA-N 0.000 description 1
- APHDVGMEAHSWTJ-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C=1OC2=C(C=1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC(=C1)C=1SC(=CC=1)C(C)(C)C)C=1SC(=CC=1)C(C)(C)C)C=C(C(=C2)OC)OC Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C=1OC2=C(C=1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC(=C1)C=1SC(=CC=1)C(C)(C)C)C=1SC(=CC=1)C(C)(C)C)C=C(C(=C2)OC)OC APHDVGMEAHSWTJ-UHFFFAOYSA-N 0.000 description 1
- KKYMKLUUSSSLAW-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C=1OC2=C(C=1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC(=C1)C=1SC(=CC=1)C(C)(C)C)C=1SC(=CC=1)C(C)(C)C)C=C(C=C2)O Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C=1OC2=C(C=1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC(=C1)C=1SC(=CC=1)C(C)(C)C)C=1SC(=CC=1)C(C)(C)C)C=C(C=C2)O KKYMKLUUSSSLAW-UHFFFAOYSA-N 0.000 description 1
- WRFXRUHPLYYKDW-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C=1OC2=C(C=1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC(=C1)C=1SC(=CC=1)C(C)(C)C)C=1SC(=CC=1)C(C)(C)C)C=C(C=C2)OCCOCCOCCOCC Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C=1OC2=C(C=1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC(=C1)C=1SC(=CC=1)C(C)(C)C)C=1SC(=CC=1)C(C)(C)C)C=C(C=C2)OCCOCCOCCOCC WRFXRUHPLYYKDW-UHFFFAOYSA-N 0.000 description 1
- OELOZAZHSGGHRV-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C=1OC2=C(C=1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC(=C1)C=1SC(=CC=1)C(C)(C)C)C=1SC(=CC=1)C(C)(C)C)C=CC=C2 Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C=1OC2=C(C=1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC(=C1)C=1SC(=CC=1)C(C)(C)C)C=1SC(=CC=1)C(C)(C)C)C=CC=C2 OELOZAZHSGGHRV-UHFFFAOYSA-N 0.000 description 1
- LZDZBJPGDUOKFU-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C=1OC2=C(C=1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC(=C1)C=1SC(=CC=1)C(C)(C)C)C=1SC(=CC=1C)C(C)(C)C)C=C(C(=C2)O)O Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C=1OC2=C(C=1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC(=C1)C=1SC(=CC=1)C(C)(C)C)C=1SC(=CC=1C)C(C)(C)C)C=C(C(=C2)O)O LZDZBJPGDUOKFU-UHFFFAOYSA-N 0.000 description 1
- DYDHAJGNTKFVTC-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C=1OC2=C(C=1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC(=C1)C=1SC(=CC=1)C(C)(C)C)C=1SC(=CC=1C)C(C)(C)C)C=C(C(=C2)OC)OC Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C=1OC2=C(C=1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC(=C1)C=1SC(=CC=1)C(C)(C)C)C=1SC(=CC=1C)C(C)(C)C)C=C(C(=C2)OC)OC DYDHAJGNTKFVTC-UHFFFAOYSA-N 0.000 description 1
- HCMQXCNMSRYXMA-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C=1OC2=C(C=1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC(=C1)C=1SC(=CC=1)C(C)(C)C)C=1SC=C(C=1)C(C)(C)C)C=C(C(=C2)O)O Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C=1OC2=C(C=1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC(=C1)C=1SC(=CC=1)C(C)(C)C)C=1SC=C(C=1)C(C)(C)C)C=C(C(=C2)O)O HCMQXCNMSRYXMA-UHFFFAOYSA-N 0.000 description 1
- MRYDHQSSLJCVGR-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C=1OC2=C(C=1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC(=C1)C=1SC(=CC=1C)C(C)(C)C)C=1SC(=CC=1C)C(C)(C)C)C=C(C(=C2)O)O Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C=1OC2=C(C=1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC(=C1)C=1SC(=CC=1C)C(C)(C)C)C=1SC(=CC=1C)C(C)(C)C)C=C(C(=C2)O)O MRYDHQSSLJCVGR-UHFFFAOYSA-N 0.000 description 1
- RYJJLGSZBKMBRO-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C=1OC2=C(C=1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC(=C1)C=1SC(=CC=1C)C(C)(C)C)C=1SC(=CC=1C)C(C)(C)C)C=C(C(=C2)OC)OC Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C=1OC2=C(C=1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC(=C1)C=1SC(=CC=1C)C(C)(C)C)C=1SC(=CC=1C)C(C)(C)C)C=C(C(=C2)OC)OC RYJJLGSZBKMBRO-UHFFFAOYSA-N 0.000 description 1
- ANWQIOGYBAXFFF-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C=1OC2=C(C=1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC(=C1)C=1SC=C(C=1)C(C)(C)C)C=1SC=C(C=1)C(C)(C)C)C=C(C(=C2)OC)OC Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C=1OC2=C(C=1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC(=C1)C=1SC=C(C=1)C(C)(C)C)C=1SC=C(C=1)C(C)(C)C)C=C(C(=C2)OC)OC ANWQIOGYBAXFFF-UHFFFAOYSA-N 0.000 description 1
- VUPYAJRIGQCGFF-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C=1OC2=C(C=1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC(=C1)C=1SC=C(C=1)C(C)(C)C)C=1SC=C(C=1)C(C)(C)C)C=C(C(=C2)OCCCC(=O)OCC)OCCCC(=O)OCC Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C=1OC2=C(C=1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC(=C1)C=1SC=C(C=1)C(C)(C)C)C=1SC=C(C=1)C(C)(C)C)C=C(C(=C2)OCCCC(=O)OCC)OCCCC(=O)OCC VUPYAJRIGQCGFF-UHFFFAOYSA-N 0.000 description 1
- CPDYXJXHAHUFCS-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C=1OC2=C(C=1C1=C(C(C(C1(F)F)(F)F)(F)F)F)C=C(C=C2)OC Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C=1OC2=C(C=1C1=C(C(C(C1(F)F)(F)F)(F)F)F)C=C(C=C2)OC CPDYXJXHAHUFCS-UHFFFAOYSA-N 0.000 description 1
- DEUPDVJTFHDUGW-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C=1OC2=C(C=1C1=C(C(C(C1(F)F)(F)F)(F)F)F)C=CC=C2 Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C=1OC2=C(C=1C1=C(C(C(C1(F)F)(F)F)(F)F)F)C=CC=C2 DEUPDVJTFHDUGW-UHFFFAOYSA-N 0.000 description 1
- TVTIVZIWPZNLLI-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(S1)C=1SC=CC=1C=1SC(=CC=1)C(C)(C)C Chemical group C(C)(C)(C)C1=CC=C(S1)C=1SC=CC=1C=1SC(=CC=1)C(C)(C)C TVTIVZIWPZNLLI-UHFFFAOYSA-N 0.000 description 1
- QIMYDAFMJLPGNV-UHFFFAOYSA-N CC(C)(C)c1ccc(-c2cc(C(C(C(C3(F)F)(F)F)(c4c-5[s]c(C(C)(C)C)c4)c4c(-c6ccc(C(C)(C)C)cc6)[o]c(cc6OCCOC)c4cc6OCCOC)=C3F)c-5[s]2)[s]1 Chemical compound CC(C)(C)c1ccc(-c2cc(C(C(C(C3(F)F)(F)F)(c4c-5[s]c(C(C)(C)C)c4)c4c(-c6ccc(C(C)(C)C)cc6)[o]c(cc6OCCOC)c4cc6OCCOC)=C3F)c-5[s]2)[s]1 QIMYDAFMJLPGNV-UHFFFAOYSA-N 0.000 description 1
- 0 CC*c(c(*)c(C)[n]1)c1O Chemical compound CC*c(c(*)c(C)[n]1)c1O 0.000 description 1
- HRXZMQYQYWUEBG-UHFFFAOYSA-N CC1(CCC(C2=C1C=C(S2)C=1SC(=CC=1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(OC2=C1C=C(C(=C2)O)O)C1=CC=C(C=C1)C(C)(C)C)C=1SC2=C(C=1)C(CCC2(C)C)(C)C)(C)C)C Chemical compound CC1(CCC(C2=C1C=C(S2)C=1SC(=CC=1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(OC2=C1C=C(C(=C2)O)O)C1=CC=C(C=C1)C(C)(C)C)C=1SC2=C(C=1)C(CCC2(C)C)(C)C)(C)C)C HRXZMQYQYWUEBG-UHFFFAOYSA-N 0.000 description 1
- SCMVLHWDOLPKOO-UHFFFAOYSA-N CC1(CCC(C2=C1C=C(S2)C=1SC(=CC=1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC2=C1C=C(C(=C2)OC)OC)C1=CC=C(C=C1)C(C)(C)C)C=1SC2=C(C=1)C(CCC2(C)C)(C)C)(C)C)C Chemical compound CC1(CCC(C2=C1C=C(S2)C=1SC(=CC=1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC2=C1C=C(C(=C2)OC)OC)C1=CC=C(C=C1)C(C)(C)C)C=1SC2=C(C=1)C(CCC2(C)C)(C)C)(C)C)C SCMVLHWDOLPKOO-UHFFFAOYSA-N 0.000 description 1
- RGDVSCLYGAPVDJ-UHFFFAOYSA-N CC1(CCC(C=2SC(=CC=21)C=1SC(=CC=1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(OC2=C1C=C(C(=C2)OCCCOC)OCCCOC)C1=CC=C(C=C1)C(C)(C)C)C1=CC2=C(S1)C(CCC2(C)C)(C)C)(C)C)C Chemical compound CC1(CCC(C=2SC(=CC=21)C=1SC(=CC=1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(OC2=C1C=C(C(=C2)OCCCOC)OCCCOC)C1=CC=C(C=C1)C(C)(C)C)C1=CC2=C(S1)C(CCC2(C)C)(C)C)(C)C)C RGDVSCLYGAPVDJ-UHFFFAOYSA-N 0.000 description 1
- ZDNAJENMTHUKPS-UHFFFAOYSA-N CCOC(=O)CCCOC1=C(C=C2C(=C1)C(=C(O2)C3=CC=C(C=C3)C(C)(C)C)C4=C(C(C(C4(F)F)(F)F)(F)F)C5=C(SC(=C5)C6=C(C=C(S6)C(C)(C)C)C)C7=C(C=C(S7)C(C)(C)C)C)OCCCC(=O)OCC Chemical compound CCOC(=O)CCCOC1=C(C=C2C(=C1)C(=C(O2)C3=CC=C(C=C3)C(C)(C)C)C4=C(C(C(C4(F)F)(F)F)(F)F)C5=C(SC(=C5)C6=C(C=C(S6)C(C)(C)C)C)C7=C(C=C(S7)C(C)(C)C)C)OCCCC(=O)OCC ZDNAJENMTHUKPS-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 1
- XTJFFFGAUHQWII-UHFFFAOYSA-N Dibutyl adipate Chemical compound CCCCOC(=O)CCCCC(=O)OCCCC XTJFFFGAUHQWII-UHFFFAOYSA-N 0.000 description 1
- VIZORQUEIQEFRT-UHFFFAOYSA-N Diethyl adipate Chemical compound CCOC(=O)CCCCC(=O)OCC VIZORQUEIQEFRT-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 1
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 1
- RDOFJDLLWVCMRU-UHFFFAOYSA-N Diisobutyl adipate Chemical compound CC(C)COC(=O)CCCCC(=O)OCC(C)C RDOFJDLLWVCMRU-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 1
- BVTJGGGYKAMDBN-UHFFFAOYSA-N Dioxetane Chemical compound C1COO1 BVTJGGGYKAMDBN-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- DJNTZVRUYMHBTD-UHFFFAOYSA-N Octyl octanoate Chemical compound CCCCCCCCOC(=O)CCCCCCC DJNTZVRUYMHBTD-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- 229920006169 Perfluoroelastomer Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 description 1
- AVRWEULSKHQETA-UHFFFAOYSA-N Thiophene-2 Chemical compound S1C=2CCCCCC=2C(C(=O)OC)=C1NC(=O)C1=C(F)C(F)=C(F)C(F)=C1F AVRWEULSKHQETA-UHFFFAOYSA-N 0.000 description 1
- FRQDZJMEHSJOPU-UHFFFAOYSA-N Triethylene glycol bis(2-ethylhexanoate) Chemical compound CCCCC(CC)C(=O)OCCOCCOCCOC(=O)C(CC)CCCC FRQDZJMEHSJOPU-UHFFFAOYSA-N 0.000 description 1
- 241000009298 Trigla lyra Species 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- IDPXMLMPPNYLBO-UHFFFAOYSA-N [5-[3-[2-[2-(4-tert-butylphenyl)-5,6-dimethoxy-1-benzofuran-3-yl]-3,3,4,4,5,5-hexafluorocyclopenten-1-yl]-5-(5-tert-butylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]-tris(3-methoxypropyl)silane Chemical compound C(C)(C)(C)C1=CC=C(S1)C1=CC(=C(S1)C=1SC(=CC=1)[Si](CCCOC)(CCCOC)CCCOC)C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(OC2=C1C=C(C(=C2)OC)OC)C1=CC=C(C=C1)C(C)(C)C IDPXMLMPPNYLBO-UHFFFAOYSA-N 0.000 description 1
- KVERUWYTWALZLU-UHFFFAOYSA-N [dimethyl(trimethylsilyloxy)silyl]oxy-dodecyl-dimethylsilane Chemical compound CCCCCCCCCCCC[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C KVERUWYTWALZLU-UHFFFAOYSA-N 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000004308 accommodation Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000005055 alkyl alkoxy group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- LKSPYOVNNMPMIZ-UHFFFAOYSA-N azete Chemical compound C1=CN=C1 LKSPYOVNNMPMIZ-UHFFFAOYSA-N 0.000 description 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
- 125000004069 aziridinyl group Chemical group 0.000 description 1
- SAOKZLXYCUGLFA-UHFFFAOYSA-N bis(2-ethylhexyl) adipate Chemical compound CCCCC(CC)COC(=O)CCCCC(=O)OCC(CC)CCCC SAOKZLXYCUGLFA-UHFFFAOYSA-N 0.000 description 1
- RSRICHZMFPHXLE-AATRIKPKSA-N bis(2-methylpropyl) (e)-but-2-enedioate Chemical compound CC(C)COC(=O)\C=C\C(=O)OCC(C)C RSRICHZMFPHXLE-AATRIKPKSA-N 0.000 description 1
- SKVONPNVOSXTBD-UHFFFAOYSA-N bis(6-methylheptyl) dodecanedioate Chemical compound CC(C)CCCCCOC(=O)CCCCCCCCCCC(=O)OCCCCCC(C)C SKVONPNVOSXTBD-UHFFFAOYSA-N 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 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
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000005676 cyclic carbonates Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- YRTMEEURRDTMST-UHFFFAOYSA-N diazetidine Chemical compound C1CNN1 YRTMEEURRDTMST-UHFFFAOYSA-N 0.000 description 1
- OGVXYCDTRMDYOG-UHFFFAOYSA-N dibutyl 2-methylidenebutanedioate Chemical compound CCCCOC(=O)CC(=C)C(=O)OCCCC OGVXYCDTRMDYOG-UHFFFAOYSA-N 0.000 description 1
- 229940100539 dibutyl adipate Drugs 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- OUWSNHWQZPEFEX-UHFFFAOYSA-N diethyl glutarate Chemical compound CCOC(=O)CCCC(=O)OCC OUWSNHWQZPEFEX-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- MJOKHGMXPJXFTG-UHFFFAOYSA-N dihexyl nonanedioate Chemical compound CCCCCCOC(=O)CCCCCCCC(=O)OCCCCCC MJOKHGMXPJXFTG-UHFFFAOYSA-N 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- UYAAVKFHBMJOJZ-UHFFFAOYSA-N diimidazo[1,3-b:1',3'-e]pyrazine-5,10-dione Chemical compound O=C1C2=CN=CN2C(=O)C2=CN=CN12 UYAAVKFHBMJOJZ-UHFFFAOYSA-N 0.000 description 1
- OEIWPNWSDYFMIL-UHFFFAOYSA-N dioctyl benzene-1,4-dicarboxylate Chemical compound CCCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCCC)C=C1 OEIWPNWSDYFMIL-UHFFFAOYSA-N 0.000 description 1
- VJHINFRRDQUWOJ-UHFFFAOYSA-N dioctyl sebacate Chemical compound CCCCC(CC)COC(=O)CCCCCCCCC(=O)OCC(CC)CCCC VJHINFRRDQUWOJ-UHFFFAOYSA-N 0.000 description 1
- LKPDARIQMYHGOW-UHFFFAOYSA-N dioxete Chemical compound C1=COO1 LKPDARIQMYHGOW-UHFFFAOYSA-N 0.000 description 1
- ASQQEOXYFGEFKQ-UHFFFAOYSA-N dioxirane Chemical compound C1OO1 ASQQEOXYFGEFKQ-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- CTGHONDBXRRMRC-UHFFFAOYSA-N dithiete Chemical compound C1=CSS1 CTGHONDBXRRMRC-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- CAMHHLOGFDZBBG-UHFFFAOYSA-N epoxidized methyl oleate Natural products CCCCCCCCC1OC1CCCCCCCC(=O)OC CAMHHLOGFDZBBG-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- SZFBZIUREPZHDO-UHFFFAOYSA-N ethyl 4-[[3-[2-[2,5-bis(5-tert-butylthiophen-2-yl)thiophen-3-yl]-3,3,4,4,5,5-hexafluorocyclopenten-1-yl]-2-(4-tert-butylphenyl)-6-(4-ethoxy-4-oxobutoxy)-1-benzofuran-5-yl]oxy]butanoate Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C=1OC2=C(C=1C1=C(C(C(C1(F)F)(F)F)(F)F)C1=C(SC(=C1)C=1SC(=CC=1)C(C)(C)C)C=1SC(=CC=1)C(C)(C)C)C=C(C(=C2)OCCCC(=O)OCC)OCCCC(=O)OCC SZFBZIUREPZHDO-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000005357 flat glass Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000001087 glyceryl triacetate Substances 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- LLEVMYXEJUDBTA-UHFFFAOYSA-N heptanedinitrile Chemical compound N#CCCCCCC#N LLEVMYXEJUDBTA-UHFFFAOYSA-N 0.000 description 1
- NFVSFLUJRHRSJG-UHFFFAOYSA-N hexadecamethylheptasiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C NFVSFLUJRHRSJG-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000005055 memory storage Effects 0.000 description 1
- 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 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- KSCKTBJJRVPGKM-UHFFFAOYSA-N octan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-] KSCKTBJJRVPGKM-UHFFFAOYSA-N 0.000 description 1
- WYNVIVRXHYGNRT-UHFFFAOYSA-N octane-3,5-diol Chemical compound CCCC(O)CC(O)CC WYNVIVRXHYGNRT-UHFFFAOYSA-N 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- SJGALSBBFTYSBA-UHFFFAOYSA-N oxaziridine Chemical compound C1NO1 SJGALSBBFTYSBA-UHFFFAOYSA-N 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- QRMPKOFEUHIBNM-UHFFFAOYSA-N p-dimethylcyclohexane Natural products CC1CCC(C)CC1 QRMPKOFEUHIBNM-UHFFFAOYSA-N 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000003140 primary amides Chemical class 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 229940116423 propylene glycol diacetate Drugs 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 150000003334 secondary amides Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000006209 tert-butylation Effects 0.000 description 1
- 150000003511 tertiary amides Chemical class 0.000 description 1
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 description 1
- HPINPCFOKNNWNW-UHFFFAOYSA-N thiete Chemical compound C1SC=C1 HPINPCFOKNNWNW-UHFFFAOYSA-N 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- WILBTFWIBAOWLN-UHFFFAOYSA-N triethyl(triethylsilyloxy)silane Chemical compound CC[Si](CC)(CC)O[Si](CC)(CC)CC WILBTFWIBAOWLN-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- YFHICDDUDORKJB-UHFFFAOYSA-N trimethylene carbonate Chemical compound O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- 239000003190 viscoelastic substance Substances 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 238000002424 x-ray crystallography Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
- C09K9/02—Organic tenebrescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201962828945P | 2019-04-03 | 2019-04-03 | |
| US62/828,945 | 2019-04-03 | ||
| PCT/CA2020/050434 WO2020198868A1 (en) | 2019-04-03 | 2020-04-02 | Photochromic and electrochromic diarylethene compounds with improved photostability and solubility |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20210148278A true KR20210148278A (ko) | 2021-12-07 |
Family
ID=72667525
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020217035733A Ceased KR20210148278A (ko) | 2019-04-03 | 2020-04-02 | 개선된 광 안정성 및 용해도를 갖는 광 변색성 및 전기 변색성 다이아릴에텐 화합물 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20220220100A1 (https=) |
| EP (1) | EP3947596A4 (https=) |
| JP (1) | JP2022528876A (https=) |
| KR (1) | KR20210148278A (https=) |
| CN (1) | CN114040959A (https=) |
| WO (1) | WO2020198868A1 (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113773311B (zh) * | 2021-09-01 | 2023-09-26 | 岭南师范学院 | 一种二噻吩乙烯化合物及其制备方法和应用 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4410108B2 (ja) * | 2002-08-09 | 2010-02-03 | スイッチ マテリアルズ インコーポレイテッド | フォトクロミックかつエレクトロクロミックな化合物、該化合物の合成方法及び該化合物の使用方法 |
| CA2609887C (en) * | 2005-05-25 | 2015-12-29 | Switch Materials Inc. | Photochromic and electrochromic compounds and synthesis and use thereof |
| CN105182569B (zh) | 2009-06-11 | 2018-08-07 | 思维奇材料公司 | 可变透光率滤光片及其应用 |
| CN101851232B (zh) * | 2010-05-31 | 2012-01-25 | 江西科技师范学院 | 光致变色异噁唑噻吩混联型全氟环戊烯化合物及合成方法和应用 |
| EP2652547B1 (en) * | 2010-12-15 | 2019-10-23 | Switch Materials, Inc. | Variable transmittance optical filter with substantially co- planar electrode system |
| KR102038447B1 (ko) | 2011-09-30 | 2019-11-29 | 스위치 머티리얼즈 인코퍼레이티드 | 디아릴에텐 화합물 및 그것의 이용 |
| US10054835B2 (en) | 2012-04-09 | 2018-08-21 | Switch Materials, Inc. | Switching materials, and compositions and methods for making same |
-
2020
- 2020-04-02 US US17/601,096 patent/US20220220100A1/en not_active Abandoned
- 2020-04-02 EP EP20784037.2A patent/EP3947596A4/en not_active Withdrawn
- 2020-04-02 WO PCT/CA2020/050434 patent/WO2020198868A1/en not_active Ceased
- 2020-04-02 CN CN202080041244.8A patent/CN114040959A/zh active Pending
- 2020-04-02 JP JP2021558857A patent/JP2022528876A/ja active Pending
- 2020-04-02 KR KR1020217035733A patent/KR20210148278A/ko not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| WO2020198868A1 (en) | 2020-10-08 |
| US20220220100A1 (en) | 2022-07-14 |
| CN114040959A (zh) | 2022-02-11 |
| EP3947596A1 (en) | 2022-02-09 |
| EP3947596A4 (en) | 2022-09-21 |
| JP2022528876A (ja) | 2022-06-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP2760969B1 (en) | Diarylethene compounds and uses thereof | |
| US6281366B1 (en) | Photochromic [3H]naphtho[2,1-b]pyran compounds containing an acetylenic substituent, process for their manufacture, and photochromic materials and articles obtained | |
| US5529725A (en) | Spirooxazines and use thereof in the field of ophthalmic optics | |
| KR20210148278A (ko) | 개선된 광 안정성 및 용해도를 갖는 광 변색성 및 전기 변색성 다이아릴에텐 화합물 | |
| JP2023076438A (ja) | ピラノキナゾリン誘導体及びナフトピラン誘導体 | |
| DE60007996T2 (de) | BI- ODER TERTHIENYL-SUBSTITUIERTE PHOTOCHROMISCHE NAPHTHO[2,1 -b]PYRANE-VERBINDUNGEN | |
| KR100303100B1 (ko) | 광호변성스피로벤조피란,이의제조방법,이를포함하는조성물및박막 | |
| EP4474446B1 (en) | Electrochromic compounds, compositions and devices comprising the same | |
| JP5217328B2 (ja) | スピロオキサジンラジカル誘導体及び可逆的異性化反応による製造方法 | |
| JP2021011441A (ja) | 有機化合物、およびそれを有するエレクトロクロミック素子、光学フィルム、レンズユニット、撮像装置、窓材 | |
| Yang | Study on novel photochromic systems based on chromophores with six-membered ring as central ethene bridge |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20211102 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20240529 Patent event code: PE09021S01D |
|
| E601 | Decision to refuse application | ||
| PE0601 | Decision on rejection of patent |
Patent event date: 20240902 Comment text: Decision to Refuse Application Patent event code: PE06012S01D |