CN108949141A - 双稳态电致变色材料的制备方法及用于制备电致变色器件 - Google Patents
双稳态电致变色材料的制备方法及用于制备电致变色器件 Download PDFInfo
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- CN108949141A CN108949141A CN201810738958.9A CN201810738958A CN108949141A CN 108949141 A CN108949141 A CN 108949141A CN 201810738958 A CN201810738958 A CN 201810738958A CN 108949141 A CN108949141 A CN 108949141A
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- Prior art keywords
- methylimidazole
- acid
- butyl
- ethyl
- methyl
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- 239000000463 material Substances 0.000 title claims abstract description 51
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 239000003513 alkali Substances 0.000 claims abstract description 46
- 239000000126 substance Substances 0.000 claims abstract description 38
- 150000004053 quinones Chemical class 0.000 claims abstract description 29
- 238000002845 discoloration Methods 0.000 claims abstract description 16
- 239000003792 electrolyte Substances 0.000 claims abstract description 16
- 239000000203 mixture Substances 0.000 claims abstract description 6
- -1 sulfonate radical Chemical group 0.000 claims description 140
- 239000002253 acid Substances 0.000 claims description 47
- 150000002466 imines Chemical class 0.000 claims description 46
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 40
- 239000002585 base Substances 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 20
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims description 19
- 230000004044 response Effects 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims description 14
- 229910052751 metal Inorganic materials 0.000 claims description 14
- 239000002184 metal Substances 0.000 claims description 14
- IBZJNLWLRUHZIX-UHFFFAOYSA-N 1-ethyl-3-methyl-2h-imidazole Chemical compound CCN1CN(C)C=C1 IBZJNLWLRUHZIX-UHFFFAOYSA-N 0.000 claims description 13
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 claims description 13
- 239000004327 boric acid Substances 0.000 claims description 13
- 239000007787 solid Substances 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 13
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 12
- 230000008859 change Effects 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 150000001450 anions Chemical class 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 238000005660 chlorination reaction Methods 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 10
- 239000001301 oxygen Chemical group 0.000 claims description 10
- XPDWGBQVDMORPB-UHFFFAOYSA-N trifluoromethane acid Natural products FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims description 10
- KAIPKTYOBMEXRR-UHFFFAOYSA-N 1-butyl-3-methyl-2h-imidazole Chemical compound CCCCN1CN(C)C=C1 KAIPKTYOBMEXRR-UHFFFAOYSA-N 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 9
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 9
- 239000002608 ionic liquid Substances 0.000 claims description 9
- PBIDWHVVZCGMAR-UHFFFAOYSA-N 1-methyl-3-prop-2-enyl-2h-imidazole Chemical compound CN1CN(CC=C)C=C1 PBIDWHVVZCGMAR-UHFFFAOYSA-N 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 229920002125 Sokalan® Polymers 0.000 claims description 8
- 150000002460 imidazoles Chemical class 0.000 claims description 8
- 150000003949 imides Chemical class 0.000 claims description 8
- 239000005416 organic matter Substances 0.000 claims description 8
- 239000004584 polyacrylic acid Substances 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 7
- 230000000996 additive effect Effects 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 229910052802 copper Inorganic materials 0.000 claims description 7
- 239000010949 copper Substances 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 229920000642 polymer Polymers 0.000 claims description 7
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 6
- 229910019142 PO4 Inorganic materials 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 239000010452 phosphate Substances 0.000 claims description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 5
- 239000005864 Sulphur Substances 0.000 claims description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 5
- 239000012528 membrane Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 238000006467 substitution reaction Methods 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 claims description 4
- IRSVMGYCAXSOCN-UHFFFAOYSA-N 1-butyl-3-methyl-1,2-dihydroimidazol-1-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.CCCC[NH+]1CN(C)C=C1 IRSVMGYCAXSOCN-UHFFFAOYSA-N 0.000 claims description 4
- FHDQNOXQSTVAIC-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;chloride Chemical compound [Cl-].CCCCN1C=C[N+](C)=C1 FHDQNOXQSTVAIC-UHFFFAOYSA-M 0.000 claims description 4
- ZXLOSLWIGFGPIU-UHFFFAOYSA-N 1-ethyl-3-methyl-1,2-dihydroimidazol-1-ium;acetate Chemical compound CC(O)=O.CCN1CN(C)C=C1 ZXLOSLWIGFGPIU-UHFFFAOYSA-N 0.000 claims description 4
- JMNFVQWMBCLWAS-UHFFFAOYSA-N C(F)(F)F.C(C)N1CN(C=C1)C Chemical compound C(F)(F)F.C(C)N1CN(C=C1)C JMNFVQWMBCLWAS-UHFFFAOYSA-N 0.000 claims description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 4
- NPGXALYHLQTILN-UHFFFAOYSA-N N1=CC=CC2=CC=CC=C12.C(C)N1CN(C=C1)C Chemical compound N1=CC=CC2=CC=CC=C12.C(C)N1CN(C=C1)C NPGXALYHLQTILN-UHFFFAOYSA-N 0.000 claims description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 239000002202 Polyethylene glycol Substances 0.000 claims description 4
- 239000004793 Polystyrene Substances 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 150000001408 amides Chemical group 0.000 claims description 4
- 150000001412 amines Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 150000003851 azoles Chemical class 0.000 claims description 4
- 230000033228 biological regulation Effects 0.000 claims description 4
- 150000001805 chlorine compounds Chemical class 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000007529 inorganic bases Chemical class 0.000 claims description 4
- 229910021645 metal ion Inorganic materials 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 150000007530 organic bases Chemical class 0.000 claims description 4
- 150000002892 organic cations Chemical class 0.000 claims description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 4
- 229920001223 polyethylene glycol Polymers 0.000 claims description 4
- 239000004926 polymethyl methacrylate Substances 0.000 claims description 4
- 229920002223 polystyrene Polymers 0.000 claims description 4
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 4
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 4
- 229910052709 silver Inorganic materials 0.000 claims description 4
- 241000894007 species Species 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 claims description 4
- ALSIFQIAIHCPAA-UHFFFAOYSA-N 1,2-dimethyl-3-propyl-2h-imidazole Chemical compound CCCN1C=CN(C)C1C ALSIFQIAIHCPAA-UHFFFAOYSA-N 0.000 claims description 3
- RTYNAJZQUQWEFN-UHFFFAOYSA-N 1,3-dimethoxy-2H-imidazole Chemical class CON1CN(C=C1)OC RTYNAJZQUQWEFN-UHFFFAOYSA-N 0.000 claims description 3
- KXCVJPJCRAEILX-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;hydrogen sulfate Chemical compound OS([O-])(=O)=O.CCCCN1C=C[N+](C)=C1 KXCVJPJCRAEILX-UHFFFAOYSA-M 0.000 claims description 3
- RILPVBCCHVYIJF-UHFFFAOYSA-N 1-ethyl-3-methyl-1,2-dihydroimidazol-1-ium;methanesulfonate Chemical compound CS(O)(=O)=O.CCN1CN(C)C=C1 RILPVBCCHVYIJF-UHFFFAOYSA-N 0.000 claims description 3
- WGVGZVWOOMIJRK-UHFFFAOYSA-N 1-hexyl-3-methyl-2h-imidazole Chemical compound CCCCCCN1CN(C)C=C1 WGVGZVWOOMIJRK-UHFFFAOYSA-N 0.000 claims description 3
- JFYZBXKLRPWSGV-UHFFFAOYSA-N 1-methyl-3-propyl-2h-imidazole Chemical compound CCCN1CN(C)C=C1 JFYZBXKLRPWSGV-UHFFFAOYSA-N 0.000 claims description 3
- XUHHZNLAPUWRHH-UHFFFAOYSA-N 3-butyl-1-methyl-1,2-dihydroimidazol-1-ium;methanesulfonate Chemical compound CS(O)(=O)=O.CCCCN1CN(C)C=C1 XUHHZNLAPUWRHH-UHFFFAOYSA-N 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 3
- IPTLKMXBROVJJF-UHFFFAOYSA-N azanium;methyl sulfate Chemical class N.COS(O)(=O)=O IPTLKMXBROVJJF-UHFFFAOYSA-N 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- ZDIRKWICVFDSNX-UHFFFAOYSA-N diethyl phosphate 1-ethyl-3-methyl-1,2-dihydroimidazol-1-ium Chemical compound P(=O)(OCC)(OCC)O.C(C)N1CN(C=C1)C ZDIRKWICVFDSNX-UHFFFAOYSA-N 0.000 claims description 3
- 239000007772 electrode material Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- NDKYLZBPBQOIRU-UHFFFAOYSA-N hexyl(tetradecyl)phosphane Chemical compound CCCCCCCCCCCCCCPCCCCCC NDKYLZBPBQOIRU-UHFFFAOYSA-N 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- TVEOIQKGZSIMNG-UHFFFAOYSA-N hydron;1-methyl-1h-imidazol-1-ium;sulfate Chemical compound OS([O-])(=O)=O.C[NH+]1C=CN=C1 TVEOIQKGZSIMNG-UHFFFAOYSA-N 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 3
- 150000001455 metallic ions Chemical class 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- PNGLEYLFMHGIQO-UHFFFAOYSA-M sodium;3-(n-ethyl-3-methoxyanilino)-2-hydroxypropane-1-sulfonate;dihydrate Chemical compound O.O.[Na+].[O-]S(=O)(=O)CC(O)CN(CC)C1=CC=CC(OC)=C1 PNGLEYLFMHGIQO-UHFFFAOYSA-M 0.000 claims description 3
- CRUUGINCUHNGMZ-UHFFFAOYSA-N 1,3-diethoxy-2h-imidazole Chemical class CCON1CN(OCC)C=C1 CRUUGINCUHNGMZ-UHFFFAOYSA-N 0.000 claims description 2
- BUMZYNVCDQOGJG-UHFFFAOYSA-N 1,3-dihydroxy-2h-imidazole Chemical class ON1CN(O)C=C1 BUMZYNVCDQOGJG-UHFFFAOYSA-N 0.000 claims description 2
- RWDGXHYBVXDRMT-UHFFFAOYSA-N 1,3-dimethoxy-2-methyl-2h-imidazole Chemical compound CON1C=CN(OC)C1C RWDGXHYBVXDRMT-UHFFFAOYSA-N 0.000 claims description 2
- MNYOKDIIUJDYBM-UHFFFAOYSA-N 1-benzyl-3-methyl-2h-imidazole Chemical compound C1=CN(C)CN1CC1=CC=CC=C1 MNYOKDIIUJDYBM-UHFFFAOYSA-N 0.000 claims description 2
- GSYBSZRLMHKNIH-UHFFFAOYSA-N 1-butyl-3-methyl-1,2-dihydroimidazol-1-ium;hydrogen carbonate Chemical compound OC([O-])=O.CCCC[NH+]1CN(C)C=C1 GSYBSZRLMHKNIH-UHFFFAOYSA-N 0.000 claims description 2
- KLFPUNSMDACYOK-UHFFFAOYSA-N 1-butyl-3-methyl-1,2-dihydroimidazol-1-ium;iodide Chemical compound [I-].CCCC[NH+]1CN(C)C=C1 KLFPUNSMDACYOK-UHFFFAOYSA-N 0.000 claims description 2
- VWFZFKKEKWMXIA-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;4-methylbenzenesulfonate Chemical compound CCCC[N+]=1C=CN(C)C=1.CC1=CC=C(S([O-])(=O)=O)C=C1 VWFZFKKEKWMXIA-UHFFFAOYSA-M 0.000 claims description 2
- WPHIMOZSRUCGGU-UHFFFAOYSA-N 1-butyl-3-methylimidazol-3-ium;nitrate Chemical compound [O-][N+]([O-])=O.CCCCN1C=C[N+](C)=C1 WPHIMOZSRUCGGU-UHFFFAOYSA-N 0.000 claims description 2
- RSJCFBORABJFGA-UHFFFAOYSA-M 1-butyl-4-methylpyridin-1-ium;iodide Chemical compound [I-].CCCC[N+]1=CC=C(C)C=C1 RSJCFBORABJFGA-UHFFFAOYSA-M 0.000 claims description 2
- KVBQNFMTEUEOCD-UHFFFAOYSA-M 1-butylpyridin-1-ium;bromide Chemical compound [Br-].CCCC[N+]1=CC=CC=C1 KVBQNFMTEUEOCD-UHFFFAOYSA-M 0.000 claims description 2
- ANTRPGYRFWBOCY-UHFFFAOYSA-N 1-ethoxy-3-methyl-2h-imidazole Chemical compound CCON1CN(C)C=C1 ANTRPGYRFWBOCY-UHFFFAOYSA-N 0.000 claims description 2
- XDZAFZVZTAGZHI-UHFFFAOYSA-N 1-ethyl-3-methyl-1,2-dihydroimidazol-1-ium;ethyl sulfate Chemical compound CCOS([O-])(=O)=O.CC[NH+]1CN(C)C=C1 XDZAFZVZTAGZHI-UHFFFAOYSA-N 0.000 claims description 2
- JCTJNVCEWUQPMB-UHFFFAOYSA-N 1-ethyl-3-methyl-1,2-dihydroimidazol-1-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.CC[NH+]1CN(C)C=C1 JCTJNVCEWUQPMB-UHFFFAOYSA-N 0.000 claims description 2
- NJMWOUFKYKNWDW-UHFFFAOYSA-N 1-ethyl-3-methylimidazolium Chemical compound CCN1C=C[N+](C)=C1 NJMWOUFKYKNWDW-UHFFFAOYSA-N 0.000 claims description 2
- UAJUIXPRXPNWPC-UHFFFAOYSA-N 2-decyl-3-methyl-1h-imidazol-3-ium;chloride Chemical compound [Cl-].CCCCCCCCCCC=1NC=C[N+]=1C UAJUIXPRXPNWPC-UHFFFAOYSA-N 0.000 claims description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 2
- HHJLGMHNXUZQSB-UHFFFAOYSA-N 3-butyl-1-methyl-1,2-dihydroimidazol-1-ium;octyl sulfate Chemical compound CCCCN1CN(C)C=C1.CCCCCCCCOS(O)(=O)=O HHJLGMHNXUZQSB-UHFFFAOYSA-N 0.000 claims description 2
- QQKICFXKOIDMSQ-UHFFFAOYSA-N 3-iodohexane Chemical compound CCCC(I)CC QQKICFXKOIDMSQ-UHFFFAOYSA-N 0.000 claims description 2
- ZVYGIPWYVVJFRW-UHFFFAOYSA-N 3-methylbutyl prop-2-enoate Chemical compound CC(C)CCOC(=O)C=C ZVYGIPWYVVJFRW-UHFFFAOYSA-N 0.000 claims description 2
- 241001502050 Acis Species 0.000 claims description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 2
- LQKFSCCYDZQDOG-UHFFFAOYSA-N C(CCC)OP(OCCCC)(O)=O.C(C)N1CN(C=C1)C Chemical compound C(CCC)OP(OCCCC)(O)=O.C(C)N1CN(C=C1)C LQKFSCCYDZQDOG-UHFFFAOYSA-N 0.000 claims description 2
- NYNXHZRPSYVEAY-UHFFFAOYSA-M C(CCC)OP(OCCCC)([O-])=O.P.C(CCC)[P+](C)(CCCC)CCCC Chemical compound C(CCC)OP(OCCCC)([O-])=O.P.C(CCC)[P+](C)(CCCC)CCCC NYNXHZRPSYVEAY-UHFFFAOYSA-M 0.000 claims description 2
- VDMGJCUCESKJNU-UHFFFAOYSA-N C(CCC)[P](CCCC)(CCCC)CCCC.CC1=CC=C(C=C1)S(=O)(=O)O Chemical compound C(CCC)[P](CCCC)(CCCC)CCCC.CC1=CC=C(C=C1)S(=O)(=O)O VDMGJCUCESKJNU-UHFFFAOYSA-N 0.000 claims description 2
- JEGLYRLAFCDWIG-UHFFFAOYSA-N C(OC)(O)=O.CN1CN(C=C1)C=C Chemical compound C(OC)(O)=O.CN1CN(C=C1)C=C JEGLYRLAFCDWIG-UHFFFAOYSA-N 0.000 claims description 2
- JPYXKBJTHPTSJX-WNQIDUERSA-M C([C@@H](O)C)(=O)[O-].CCO[N+](C)(C)C Chemical compound C([C@@H](O)C)(=O)[O-].CCO[N+](C)(C)C JPYXKBJTHPTSJX-WNQIDUERSA-M 0.000 claims description 2
- PJKVXIZOGDGCCF-UHFFFAOYSA-N CCCCC(CCCC)(CCCC)S(OCCCC)(=O)=O.N Chemical compound CCCCC(CCCC)(CCCC)S(OCCCC)(=O)=O.N PJKVXIZOGDGCCF-UHFFFAOYSA-N 0.000 claims description 2
- WGYDNLVXIPEXMS-UHFFFAOYSA-N CCCCCCCCCCCCCCCCCCCC.P.Br Chemical class CCCCCCCCCCCCCCCCCCCC.P.Br WGYDNLVXIPEXMS-UHFFFAOYSA-N 0.000 claims description 2
- NVRJGEFEUPOTOF-UHFFFAOYSA-N CCCCCCCCP(CCCCCCCC)C(C)CCCCCCC.OC(C1=CC=CC=C1S)=O.N Chemical compound CCCCCCCCP(CCCCCCCC)C(C)CCCCCCC.OC(C1=CC=CC=C1S)=O.N NVRJGEFEUPOTOF-UHFFFAOYSA-N 0.000 claims description 2
- PJOVIZMLOFBDEC-UHFFFAOYSA-N CCCCOP(O)(OC(C)CCC(CC)(CC)CC)=O.N Chemical compound CCCCOP(O)(OC(C)CCC(CC)(CC)CC)=O.N PJOVIZMLOFBDEC-UHFFFAOYSA-N 0.000 claims description 2
- DPPQAXHEOOBPBK-UHFFFAOYSA-M CCCCOP([O-])(OCCCC)=O.CCCC[P+](C)(CCCC)CCCC.N Chemical compound CCCCOP([O-])(OCCCC)=O.CCCC[P+](C)(CCCC)CCCC.N DPPQAXHEOOBPBK-UHFFFAOYSA-M 0.000 claims description 2
- SAWKSTDLGNVFDJ-UHFFFAOYSA-M CCCC[P+](C)(CCCC)CCCC.COC([O-])=O.N Chemical compound CCCC[P+](C)(CCCC)CCCC.COC([O-])=O.N SAWKSTDLGNVFDJ-UHFFFAOYSA-M 0.000 claims description 2
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- 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
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/15—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on an electrochromic effect
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
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- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
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CN110133934A (zh) * | 2019-05-31 | 2019-08-16 | 电子科技大学 | 一种双稳态电致变色器件及其制备方法 |
CN112521619A (zh) * | 2020-11-13 | 2021-03-19 | 太原理工大学 | 一种阴离子后置换绿色合成MIL-101(Cr)-X-的方法 |
CN114015433A (zh) * | 2021-12-01 | 2022-02-08 | 吉林大学 | 一种电致变色材料、器件及其制备方法 |
CN115010836A (zh) * | 2022-06-08 | 2022-09-06 | 吉林大学 | 一种电致荧光变色聚合物和纳米粒子及器件 |
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110133934A (zh) * | 2019-05-31 | 2019-08-16 | 电子科技大学 | 一种双稳态电致变色器件及其制备方法 |
CN112521619A (zh) * | 2020-11-13 | 2021-03-19 | 太原理工大学 | 一种阴离子后置换绿色合成MIL-101(Cr)-X-的方法 |
CN112521619B (zh) * | 2020-11-13 | 2022-04-01 | 太原理工大学 | 一种阴离子后置换绿色合成MIL-101(Cr)-X-的方法 |
CN114015433A (zh) * | 2021-12-01 | 2022-02-08 | 吉林大学 | 一种电致变色材料、器件及其制备方法 |
CN114015433B (zh) * | 2021-12-01 | 2024-04-19 | 吉林大学 | 一种电致变色材料、器件及其制备方法 |
CN115010836A (zh) * | 2022-06-08 | 2022-09-06 | 吉林大学 | 一种电致荧光变色聚合物和纳米粒子及器件 |
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