CA1173864A - Bis(p-alkylphenylethynyl)anthracenes - Google Patents
Bis(p-alkylphenylethynyl)anthracenesInfo
- Publication number
- CA1173864A CA1173864A CA000413070A CA413070A CA1173864A CA 1173864 A CA1173864 A CA 1173864A CA 000413070 A CA000413070 A CA 000413070A CA 413070 A CA413070 A CA 413070A CA 1173864 A CA1173864 A CA 1173864A
- Authority
- CA
- Canada
- Prior art keywords
- bis
- compound
- fluorescer
- peroxide
- mixtures
- 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
Links
- 150000001454 anthracenes Chemical class 0.000 title abstract description 3
- 239000000203 mixture Substances 0.000 claims abstract description 39
- 150000002978 peroxides Chemical class 0.000 claims description 23
- 239000000376 reactant Substances 0.000 claims description 17
- 239000003085 diluting agent Substances 0.000 claims description 13
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 6
- XAMSREXGFXRHLD-UHFFFAOYSA-N 9,10-bis[2-(4-octylphenyl)ethynyl]anthracene Chemical compound C1=CC(CCCCCCCC)=CC=C1C#CC(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C#CC1=CC=C(CCCCCCCC)C=C1 XAMSREXGFXRHLD-UHFFFAOYSA-N 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 abstract description 10
- 238000006862 quantum yield reaction Methods 0.000 abstract description 4
- 239000002243 precursor Substances 0.000 abstract 1
- 239000008247 solid mixture Substances 0.000 abstract 1
- 239000011877 solvent mixture Substances 0.000 abstract 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Substances OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 30
- 150000001875 compounds Chemical class 0.000 description 29
- 239000000306 component Substances 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 11
- 235000013350 formula milk Nutrition 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- -1 hydrogen peroxide compound Chemical class 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical group CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 4
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- ZHBOFZNNPZNWGB-UHFFFAOYSA-N 9,10-bis(phenylethynyl)anthracene Chemical group C1=CC=CC=C1C#CC(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C#CC1=CC=CC=C1 ZHBOFZNNPZNWGB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ABBQHOQBGMUPJH-UHFFFAOYSA-M Sodium salicylate Chemical compound [Na+].OC1=CC=CC=C1C([O-])=O ABBQHOQBGMUPJH-UHFFFAOYSA-M 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229960004025 sodium salicylate Drugs 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- XZKOELJOFVHXRS-UHFFFAOYSA-N 1,1,1,2,2,3,3-heptafluoro-3-(1,1,2,2,3,3,3-heptafluoropropoxy)propane Chemical compound FC(F)(F)C(F)(F)C(F)(F)OC(F)(F)C(F)(F)C(F)(F)F XZKOELJOFVHXRS-UHFFFAOYSA-N 0.000 description 1
- DYZYNUQMTZWZAO-UHFFFAOYSA-N 1-(2-phenylethynyl)anthracene Chemical compound C1=CC=CC=C1C#CC1=CC=CC2=CC3=CC=CC=C3C=C12 DYZYNUQMTZWZAO-UHFFFAOYSA-N 0.000 description 1
- IUPJHZHRXLYZBR-UHFFFAOYSA-N 1-dodecyl-4-ethynylbenzene Chemical group CCCCCCCCCCCCC1=CC=C(C#C)C=C1 IUPJHZHRXLYZBR-UHFFFAOYSA-N 0.000 description 1
- FPSPMWQTTQJAGI-UHFFFAOYSA-N 1-ethynyl-4-octylbenzene Chemical group CCCCCCCCC1=CC=C(C#C)C=C1 FPSPMWQTTQJAGI-UHFFFAOYSA-N 0.000 description 1
- AOPDRZXCEAKHHW-UHFFFAOYSA-N 1-pentoxypentane Chemical compound CCCCCOCCCCC AOPDRZXCEAKHHW-UHFFFAOYSA-N 0.000 description 1
- WEFYTUJDZBLKSR-UHFFFAOYSA-N 5-(2-hydroxyethoxymethyl)nonan-5-ol Chemical compound CCCCC(O)(CCCC)COCCO WEFYTUJDZBLKSR-UHFFFAOYSA-N 0.000 description 1
- BLSSDZUTDBAKJF-UHFFFAOYSA-N 9,10-bis[2-(4-butylphenyl)ethynyl]anthracene Chemical compound C1=CC(CCCC)=CC=C1C#CC(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C#CC1=CC=C(CCCC)C=C1 BLSSDZUTDBAKJF-UHFFFAOYSA-N 0.000 description 1
- OSWFGUMWMLEWLV-UHFFFAOYSA-N 9,10-bis[2-(4-hexylphenyl)ethynyl]anthracene Chemical compound C1=CC(CCCCCC)=CC=C1C#CC(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C#CC1=CC=C(CCCCCC)C=C1 OSWFGUMWMLEWLV-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical class NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- ACSAXAVXMIBGBK-UHFFFAOYSA-N [NH2-].[Li+].C(CCCCCCC)C1=CC=C(C=C1)C#CC=1C2=CC=CC=C2C(=C2C=CC=CC12)C#CC1=CC=C(C=C1)CCCCCCCC Chemical compound [NH2-].[Li+].C(CCCCCCC)C1=CC=C(C=C1)C#CC=1C2=CC=CC=C2C(=C2C=CC=CC12)C#CC1=CC=C(C=C1)CCCCCCCC ACSAXAVXMIBGBK-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- TZZLVFUOAYMTHA-UHFFFAOYSA-N bis-(2,4,5-trichloro-6-(pentyloxycarbonyl)phenyl)oxalate Chemical compound CCCCCOC(=O)C1=C(Cl)C(Cl)=CC(Cl)=C1OC(=O)C(=O)OC1=C(Cl)C=C(Cl)C(Cl)=C1C(=O)OCCCCC TZZLVFUOAYMTHA-UHFFFAOYSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- 229960001826 dimethylphthalate Drugs 0.000 description 1
- SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 150000003901 oxalic acid esters Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
- C09K11/07—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials having chemically interreactive components, e.g. reactive chemiluminescent compositions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
- C07C15/56—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic condensed
- C07C15/60—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic condensed containing three rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Luminescent Compositions (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US341,390 | 1982-01-21 | ||
| US06/341,390 US4401585A (en) | 1982-01-21 | 1982-01-21 | Bis(p-alkylphenylethynyl)anthracene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1173864A true CA1173864A (en) | 1984-09-04 |
Family
ID=23337350
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000413070A Expired CA1173864A (en) | 1982-01-21 | 1982-10-07 | Bis(p-alkylphenylethynyl)anthracenes |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4401585A (enExample) |
| EP (1) | EP0084599B1 (enExample) |
| JP (1) | JPS58128328A (enExample) |
| KR (1) | KR900003429B1 (enExample) |
| AT (1) | ATE13313T1 (enExample) |
| CA (1) | CA1173864A (enExample) |
| DE (1) | DE3263554D1 (enExample) |
| ES (1) | ES519044A0 (enExample) |
| GB (1) | GB2113709B (enExample) |
| HK (1) | HK39089A (enExample) |
| IL (1) | IL66948A0 (enExample) |
| NO (1) | NO155879C (enExample) |
| SG (1) | SG86688G (enExample) |
| ZA (1) | ZA83397B (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3362697D1 (de) * | 1982-10-25 | 1986-04-30 | American Cyanamid Co | 9,10-bis(phenylethynyl)-anthracenes |
| US4655969A (en) * | 1985-04-03 | 1987-04-07 | Richter Herbert P | Chemiluminescent systems |
| US4626383A (en) * | 1985-04-03 | 1986-12-02 | The United States Of America As Represented By The Secretary Of The Navy | Chemiluminescent system catalysts |
| US4717511A (en) * | 1985-12-26 | 1988-01-05 | American Cyanamid Company | Chemiluminescent composition |
| US4698183A (en) * | 1986-02-04 | 1987-10-06 | American Cyanamid Company | High light output-short duration chemiluminescent compositions |
| JPH01124397A (ja) * | 1987-11-09 | 1989-05-17 | Teijin Ltd | アスペルギルスに対するヒト・モノクローナル抗体とその製造法 |
| JP2800845B2 (ja) * | 1990-10-29 | 1998-09-21 | 山本化成株式会社 | アントラセン誘導体 |
| US5597517A (en) * | 1996-04-30 | 1997-01-28 | Jame Fine Chemicals, Inc. | Two-component chemiluminescent composition |
| JP3902993B2 (ja) | 2002-08-27 | 2007-04-11 | キヤノン株式会社 | フルオレン化合物及びそれを用いた有機発光素子 |
| US6852429B1 (en) | 2003-08-06 | 2005-02-08 | Canon Kabushiki Kaisha | Organic electroluminescent device based on pyrene derivatives |
| US7195829B2 (en) | 2004-03-30 | 2007-03-27 | Eastman Kodak Company | Organic element for electroluminescent devices |
| US20060214141A1 (en) * | 2005-03-23 | 2006-09-28 | Yankielun Norbert E | Luminescent illumination adjunct for night vision |
| US20080128666A1 (en) * | 2005-12-13 | 2008-06-05 | Crayola, Llc | Chemiluminescent system |
| US20070134513A1 (en) * | 2005-12-13 | 2007-06-14 | Binney & Smith | Chemiluminescent system |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3557233A (en) * | 1968-03-14 | 1971-01-19 | American Cyanamid Co | Aromatic hydrocarbons substituted by phenylethynyl groups |
| SE369187B (enExample) * | 1969-04-07 | 1974-08-12 | American Cyanamid Co | |
| US3729426A (en) * | 1970-04-20 | 1973-04-24 | American Cyanamid Co | Chemiluminescent fluorescer comprising phenylethynyl substituted organic compounds |
| CA1015555A (en) * | 1972-06-12 | 1977-08-16 | American Cyanamid Company | Chlorinated bis(phenylethynyl)anthracenes as fluorescers in chemiluminescent systems |
| US3888786A (en) * | 1972-06-12 | 1975-06-10 | American Cyanamid Co | Chlorinated bis(phenylethynyl)anthracenes as fluorescers in chemiluminescent systems |
| US4076645A (en) * | 1977-01-10 | 1978-02-28 | American Cyanamid Company | Chemical lighting process and composition |
-
1982
- 1982-01-21 US US06/341,390 patent/US4401585A/en not_active Expired - Fee Related
- 1982-09-30 DE DE8282109051T patent/DE3263554D1/de not_active Expired
- 1982-09-30 AT AT82109051T patent/ATE13313T1/de active
- 1982-09-30 EP EP82109051A patent/EP0084599B1/en not_active Expired
- 1982-10-07 CA CA000413070A patent/CA1173864A/en not_active Expired
- 1982-10-08 IL IL66948A patent/IL66948A0/xx not_active IP Right Cessation
- 1982-10-22 GB GB08230188A patent/GB2113709B/en not_active Expired
- 1982-12-24 KR KR8205797A patent/KR900003429B1/ko not_active Expired
-
1983
- 1983-01-17 ES ES519044A patent/ES519044A0/es active Granted
- 1983-01-17 JP JP58004277A patent/JPS58128328A/ja active Granted
- 1983-01-20 NO NO830181A patent/NO155879C/no unknown
- 1983-01-20 ZA ZA83397A patent/ZA83397B/xx unknown
-
1988
- 1988-12-08 SG SG866/88A patent/SG86688G/en unknown
-
1989
- 1989-05-11 HK HK390/89A patent/HK39089A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES8501431A1 (es) | 1984-12-16 |
| KR840002887A (ko) | 1984-07-21 |
| GB2113709B (en) | 1986-06-11 |
| KR900003429B1 (ko) | 1990-05-18 |
| HK39089A (en) | 1989-05-19 |
| ZA83397B (en) | 1983-10-26 |
| ES519044A0 (es) | 1984-12-16 |
| ATE13313T1 (de) | 1985-06-15 |
| SG86688G (en) | 1989-05-26 |
| JPS58128328A (ja) | 1983-07-30 |
| EP0084599B1 (en) | 1985-05-15 |
| US4401585A (en) | 1983-08-30 |
| NO155879C (no) | 1987-06-17 |
| JPH0322852B2 (enExample) | 1991-03-27 |
| DE3263554D1 (en) | 1985-06-20 |
| IL66948A0 (en) | 1983-02-23 |
| NO830181L (no) | 1983-07-22 |
| GB2113709A (en) | 1983-08-10 |
| EP0084599A1 (en) | 1983-08-03 |
| NO155879B (no) | 1987-03-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1173864A (en) | Bis(p-alkylphenylethynyl)anthracenes | |
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| JPS6331463B2 (enExample) | ||
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