WO2002104072A2 - Emissive multichromophoric systems - Google Patents
Emissive multichromophoric systems Download PDFInfo
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- WO2002104072A2 WO2002104072A2 PCT/US2002/005584 US0205584W WO02104072A2 WO 2002104072 A2 WO2002104072 A2 WO 2002104072A2 US 0205584 W US0205584 W US 0205584W WO 02104072 A2 WO02104072 A2 WO 02104072A2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/361—Polynuclear complexes, i.e. complexes comprising two or more metal centers
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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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
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1408—Carbocyclic compounds
- C09K2211/1416—Condensed systems
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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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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1408—Carbocyclic compounds
- C09K2211/1425—Non-condensed systems
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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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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1441—Heterocyclic
- C09K2211/1466—Heterocyclic containing nitrogen as the only heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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- C—CHEMISTRY; METALLURGY
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/18—Deposition of organic active material using non-liquid printing techniques, e.g. thermal transfer printing from a donor sheet
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/381—Metal complexes comprising a group IIB metal element, e.g. comprising cadmium, mercury or zinc
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- H—ELECTRICITY
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- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
Definitions
- Emission spectra obtained for the chromophore are corrected to account for the wavelength-dependent efficiency of the detection system which can be determined using the spectral output of a calibrated light source obtained from the National Bureau of Standards.
- Secondary corrections to the emission spectra used to determine QYs are performed as outlined by Lakowicz[Lakowicz, 1983]. Quantum yields are determined typically using two standard benchmarks for each chromophore.
- the compound exhibits an integral emission oscillator strength that is greater than a sum of emission oscillator strengths exhibited by its component moieties.
- Representative moieties are those that include a conjugated ring system.
- Benchmark fluorescence emitters utilized were [dye (QY; solvent; ⁇ « ⁇ (nm))]: (i) TPPZn (0.033; benzene; (598, 647)); (ii) TPPZn (0.028; 10:1
- porphyrins of the invention can be incorporated into virtually any polymeric matrix known in the art, including but not limited to polyacetylenes, polyimides, polyacrylates, polyolefins, pohyethers, polyurethanes, polyquinolines, polycarbonates, polyanilines, polypyrroles, and polythiophenes.
- fluorescent porphyrins can be incorporated into such polymers as end-capping groups.
- the conjugated synthetic multichromophoric systems of the invention can be used, for example, as dyes, catalysts, contrast agents, antitumor agents, antiviral agents, liquid crystals, electroluminescent materials, LEDs, lasers, photorefractive materials, in chemical sensors and in electrooptical and solar energy conversion devices. They also can be incorporated into supramolecular structures.
- Pd(PPh3)4 (0.02 mmol) are dissolved in 25 ml dry THF. A solution of cis-bis(tri-n-butyltin)- 1 ,2-difluoroethene (0.2 mmol) in 5 ml THF is added and the solution heated at reflux for 2 days. The reaction is quenched with water, extracted with methylene chloride, dried over calcium chloride, and the solvents evaporated.
- the crude solid is chromatographed on silica using methylene chloride/hexane eluant to isolate the Cofacial-bis-[cis-ethenyl meso-bridged]zinc po ⁇ hyrin complex of formula (5) and Polymeric-bis-[cisethenyl meso-bridged] porphyrin species of formula (6), wherein R ⁇ , and R / 4 3 are phenyl and M is Zn.
- This halogenated fluorophore, lumophore, or phosphore is now subjected to a metal catalyzed cross-coupling reaction which results in the formation of an ethyne bond at the atomic position that bore the above said halogen moiety.
- This ethynylated fluorophore, lumophore, or phosphore is now subjected to a second metal-catalyzed cross-coupling reaction with the above said halogenated fluorophore, lumophore, or phosphore under conditions appropriate to produce an ethyne-bridged bis(fluorophore, lumophore, or phosphore) compound, in which the ethyne moiety connects the two component emissive moieties along a vector that is defined by, or approximates, the head-to-tail alignment of their two respective transition dipoles.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- High Energy & Nuclear Physics (AREA)
- Inorganic Chemistry (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
- Led Devices (AREA)
- Light Receiving Elements (AREA)
- Luminescent Compositions (AREA)
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2003506242A JP2005503453A (en) | 2001-02-26 | 2002-02-26 | Luminescent multicolor chromophore system |
US10/467,107 US20040067198A1 (en) | 2002-02-26 | 2002-02-26 | Emissive multichromophoric systems |
EP02763188A EP1363916A4 (en) | 2001-02-26 | 2002-02-26 | Emissive multichromophoric systems |
AU2002327166A AU2002327166A1 (en) | 2001-02-26 | 2002-02-26 | Emissive multichromophoric systems |
CA002439060A CA2439060A1 (en) | 2001-02-26 | 2002-02-26 | Emissive multichromophoric systems |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US27152001P | 2001-02-26 | 2001-02-26 | |
US60/271,520 | 2001-02-26 | ||
US30650401P | 2001-07-19 | 2001-07-19 | |
US60/306,504 | 2001-07-19 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2002104072A2 true WO2002104072A2 (en) | 2002-12-27 |
WO2002104072A3 WO2002104072A3 (en) | 2003-06-05 |
Family
ID=26954969
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2002/005584 WO2002104072A2 (en) | 2001-02-26 | 2002-02-26 | Emissive multichromophoric systems |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP1363916A4 (en) |
JP (2) | JP2005503453A (en) |
AU (1) | AU2002327166A1 (en) |
CA (1) | CA2439060A1 (en) |
WO (1) | WO2002104072A2 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007500192A (en) * | 2003-07-25 | 2007-01-11 | ザ・トラスティーズ・オブ・ザ・ユニバーシティ・オブ・ペンシルバニア | Polymersomes combined with highly radioactive probes |
JP2008505894A (en) * | 2004-07-08 | 2008-02-28 | ノース・キャロライナ・ステイト・ユニヴァーシティ | Synthesis of porphyrins designed to bind to electroactive surfaces via carbon chains. |
EP2068141A3 (en) * | 2004-09-10 | 2017-12-27 | BAM Bundesanstalt für Materialforschung und -prüfung | Method and kit for calibration of a photoluminescence measuring system |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10510914B2 (en) | 2013-03-21 | 2019-12-17 | Board Of Trustees Of Michigan State University | Transparent energy-harvesting devices |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5798306A (en) * | 1996-04-17 | 1998-08-25 | Corning Incorporated | Rare earth doped oxyhalide laser glass |
US5986090A (en) * | 1992-08-14 | 1999-11-16 | The Trustees Of The University Of Pennsylvania | Metal-mediated cross-coupling with ring-metalated porphyrins |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH07113031B2 (en) * | 1989-12-15 | 1995-12-06 | 財団法人生産開発科学研究所 | Porphyrin multimer and method for producing the same |
US5599924A (en) * | 1992-08-14 | 1997-02-04 | Trustees Of The University Of Pennsylvania | Electron-deficient porphyrins and processes and intermediates for preparing same |
JP3150948B2 (en) * | 1998-09-21 | 2001-03-26 | 科学技術振興事業団 | Meso-position porphyrin polymer and method for producing the same |
TW528789B (en) * | 2000-12-22 | 2003-04-21 | Koninkl Philips Electronics Nv | Electroluminescent device comprising an electroluminescent material of at least two metal chelates |
-
2002
- 2002-02-26 AU AU2002327166A patent/AU2002327166A1/en not_active Abandoned
- 2002-02-26 CA CA002439060A patent/CA2439060A1/en not_active Abandoned
- 2002-02-26 EP EP02763188A patent/EP1363916A4/en not_active Ceased
- 2002-02-26 WO PCT/US2002/005584 patent/WO2002104072A2/en active Application Filing
- 2002-02-26 JP JP2003506242A patent/JP2005503453A/en active Pending
-
2007
- 2007-05-14 JP JP2007127762A patent/JP2007221168A/en active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5986090A (en) * | 1992-08-14 | 1999-11-16 | The Trustees Of The University Of Pennsylvania | Metal-mediated cross-coupling with ring-metalated porphyrins |
US5798306A (en) * | 1996-04-17 | 1998-08-25 | Corning Incorporated | Rare earth doped oxyhalide laser glass |
Non-Patent Citations (1)
Title |
---|
See also references of EP1363916A2 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007500192A (en) * | 2003-07-25 | 2007-01-11 | ザ・トラスティーズ・オブ・ザ・ユニバーシティ・オブ・ペンシルバニア | Polymersomes combined with highly radioactive probes |
JP2008505894A (en) * | 2004-07-08 | 2008-02-28 | ノース・キャロライナ・ステイト・ユニヴァーシティ | Synthesis of porphyrins designed to bind to electroactive surfaces via carbon chains. |
EP2068141A3 (en) * | 2004-09-10 | 2017-12-27 | BAM Bundesanstalt für Materialforschung und -prüfung | Method and kit for calibration of a photoluminescence measuring system |
Also Published As
Publication number | Publication date |
---|---|
AU2002327166A1 (en) | 2003-01-02 |
WO2002104072A3 (en) | 2003-06-05 |
EP1363916A4 (en) | 2006-06-28 |
EP1363916A2 (en) | 2003-11-26 |
CA2439060A1 (en) | 2002-12-27 |
JP2005503453A (en) | 2005-02-03 |
JP2007221168A (en) | 2007-08-30 |
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