CN1219018C - 具有星射型结构的红色荧光染料及其合成方法与用途 - Google Patents
具有星射型结构的红色荧光染料及其合成方法与用途 Download PDFInfo
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- CN1219018C CN1219018C CN 02146048 CN02146048A CN1219018C CN 1219018 C CN1219018 C CN 1219018C CN 02146048 CN02146048 CN 02146048 CN 02146048 A CN02146048 A CN 02146048A CN 1219018 C CN1219018 C CN 1219018C
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- 239000007850 fluorescent dye Substances 0.000 title abstract description 14
- 239000000975 dye Substances 0.000 claims abstract description 44
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- 238000001035 drying Methods 0.000 claims abstract description 11
- -1 triphenylamine aldehyde Chemical class 0.000 claims abstract description 8
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 51
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 24
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
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- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- 125000002837 carbocyclic group Chemical group 0.000 claims description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
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- 229960005181 morphine Drugs 0.000 claims description 2
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- 238000002189 fluorescence spectrum Methods 0.000 abstract description 3
- 238000001429 visible spectrum Methods 0.000 abstract description 3
- RCAFEQWFDGXVLJ-UHFFFAOYSA-N 2-(2-methylpyran-4-ylidene)propanedinitrile Chemical class CC1=CC(=C(C#N)C#N)C=CO1 RCAFEQWFDGXVLJ-UHFFFAOYSA-N 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000002386 leaching Methods 0.000 abstract 1
- 238000001308 synthesis method Methods 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 30
- 230000000171 quenching effect Effects 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 229920002554 vinyl polymer Polymers 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- 239000000370 acceptor Substances 0.000 description 8
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- 238000001816 cooling Methods 0.000 description 8
- 238000001819 mass spectrum Methods 0.000 description 8
- 230000005311 nuclear magnetism Effects 0.000 description 8
- 238000010025 steaming Methods 0.000 description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 8
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- DTZWGKCFKSJGPK-VOTSOKGWSA-N (e)-2-(2-methyl-6-(2-(1,1,7,7-tetramethyl-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinolin-9-yl)vinyl)-4h-pyran-4-ylidene)malononitrile Chemical compound O1C(C)=CC(=C(C#N)C#N)C=C1\C=C\C1=CC(C(CCN2CCC3(C)C)(C)C)=C2C3=C1 DTZWGKCFKSJGPK-VOTSOKGWSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
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- 229910052782 aluminium Inorganic materials 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
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- 239000005977 Ethylene Substances 0.000 description 1
- BZORFPDSXLZWJF-UHFFFAOYSA-N N,N-dimethyl-1,4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
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- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 230000008859 change Effects 0.000 description 1
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- 239000008367 deionised water Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 238000001506 fluorescence spectroscopy Methods 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- DZFWNZJKBJOGFQ-UHFFFAOYSA-N julolidine Chemical class C1CCC2=CC=CC3=C2N1CCC3 DZFWNZJKBJOGFQ-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
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- 239000011159 matrix material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
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- 239000002798 polar solvent Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
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- Electroluminescent Light Sources (AREA)
Abstract
Description
化合物 | 最大吸收波长(nm) | 最大荧光波长(nm) | 荧光量子产率* | ||
固体薄膜 | 氯仿溶液 | 固体薄膜 | 氯仿溶液 | ||
实施例1实施例2实施例5实施例6 | 489512517535 | 475501507512 | 632635621656 | 611615608621 | 0.540.770.870.75 |
Claims (9)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 02146048 CN1219018C (zh) | 2002-10-28 | 2002-10-28 | 具有星射型结构的红色荧光染料及其合成方法与用途 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 02146048 CN1219018C (zh) | 2002-10-28 | 2002-10-28 | 具有星射型结构的红色荧光染料及其合成方法与用途 |
Publications (2)
Publication Number | Publication Date |
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CN1493645A CN1493645A (zh) | 2004-05-05 |
CN1219018C true CN1219018C (zh) | 2005-09-14 |
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CN 02146048 Expired - Fee Related CN1219018C (zh) | 2002-10-28 | 2002-10-28 | 具有星射型结构的红色荧光染料及其合成方法与用途 |
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CN (1) | CN1219018C (zh) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1317334C (zh) * | 2004-05-20 | 2007-05-23 | 中国科学院化学研究所 | 一种分子内电荷转移型荧光染料及其应用 |
CN1293164C (zh) * | 2004-06-11 | 2007-01-03 | 中国科学院化学研究所 | 具有电荷转移结构的主体型红色发光材料及制法和应用 |
CN100389168C (zh) * | 2006-04-04 | 2008-05-21 | 吉林大学 | 基底诱导同一染料分子发不同颜色荧光的方法 |
AU2013354896A1 (en) * | 2012-12-04 | 2015-07-09 | The University Of Queensland | Method for the detection of analytes via luminescence quenching |
-
2002
- 2002-10-28 CN CN 02146048 patent/CN1219018C/zh not_active Expired - Fee Related
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PB01 | Publication | ||
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SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
EE01 | Entry into force of recordation of patent licensing contract |
Assignee: ZHEJIANG OSI CHEMISTRY Co.,Ltd. Assignor: Technical Institute of Physics and Chemistry Chinese Academy of Sciences Contract fulfillment period: 2007.6.18 to 2012.6.18 Contract record no.: 2008330000706 Denomination of invention: Red fluorescent dye possessing star project type structure and its synthesis method and use Granted publication date: 20050914 License type: Exclusive license Record date: 20080927 |
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LIC | Patent licence contract for exploitation submitted for record |
Free format text: EXCLUSIVE LICENCE; TIME LIMIT OF IMPLEMENTING CONTACT: 2007.6.18 TO 2012.6.18 Name of requester: ZHEJIANG AOSHI CHEMICAL CO., LTD. Effective date: 20080927 |
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Granted publication date: 20050914 Termination date: 20091130 |