Investigation of reactivity of organic radical cations in solution and at interface.

2006 Fiscal Year Final Research Report Summary

• Project/Area Number: 14050008
• Research Category: Grant-in-Aid for Scientific Research on Priority Areas
• Allocation Type: Single-year Grants
• Review Section: Science and Engineering
• Research Institution: Osaka Prefecture University (2006); Tohoku University (2002-2005)
• Principal Investigator: IKEDA Hiroshi Osaka Prefecture University, Graduate School of Engineering, Department of Applied Chemistry, Associate Professor (30211717)
• Project Period (FY): 2001 – 2006
• Keywords: Photochemistry / Zeolite / Electron Transfer Reaction / Reaction Mechanism / Radical Cation / Biradical / Thermoluminescence / OLED

Research Abstract

1. Investigation of Electronic Structures and Molecular Structures of Radical Cations Generated in Photoinduced Electron-Transfer.
The electronic structures and molecular structures of radical cations generated in photoinduced electron-transfer (PET) was investigated by using organic and physical chemical experiments and theoretical calculations.
As a result, we discovered a novel oxatetramethyleneethane radical cation, a distonic radical cation with or without orbital interaction, and nonclassical radical cation. In addition, we studied the observation of the excited biradical and its orbital interaction by using thennoluminescence. We found out that thennoluminescence is an effective tool of the observation of the transient intermediate that was rarely observed by absorption spectroscopy.
2. A new organic functionalization of the zeolite surface oriented toward a photofunctionalized interface.
We found that an HZSM-5-induced electron-transfer reaction of methylenecyclopropane derivative resulted in the formation of a persistent radical cation stabilized in an HZSM-5.
3. Investigation of the mechanism of thermoluminescence of the open-shell species and development of organic light-emitting diodes (OLED).
(I) Investigation of the mechanism of thermoluminescence of the open-shell species. The mechanism of the thenmoluminescence of methylenecyclopropane was studied. As a result, it was found that the thermoluminescence was originated from the excited state of trimethylenemethane biradical that is formed by back electron transfer from the substrate radical anion to the corresponding radical cation.
(2) Development of Organic light-emitting Diodes (OLED). Next, a new concept of organic radical light-emitting diodes (ORLED), a new OLED using an electronically excited triplet trimethylenemethane biradical, is proposed. The mechanistic features of ORLED have the potential of overcoming significant problems (e. g. difficulty obtaining long wavelength emission, low quantum efficiency, and low device durability) associated with typical OLED that use organic closed-shell hydrocarbons. In fact, we manufactured a bilayer OLED using a methylenecyclopropane compound as a dopant and observed a electroluminescence from the corresponding excited biradical.

Research Products

• [Journal Article] The Facile Generation of a Tetramethyleneethane Type Radical Cation and Biradical Utilizing a 3, 4-Di(α-styry1)furan and a Photoinduced ET and Back ET Sequence (2008)
  • Author(s): Ikeda, T., Ikeda, H., Takahashi, Y., Yamada, M., Mizuno, K., Tero-Kubota, S., Yamauchi, S.
  • Journal Title: J. Am. Chem. Soc. 130 Pages: 2466-2472
  • Description: 「研究成果報告書概要(和文)」より
  • Peer Reviewed
• [Journal Article] The Reaction Mechanism for the High Quantum Yield of the Cypridina (Vargula) Bioluminescence Supported by Chemiluminescence of 6-Ary1-2-methylimidazo[1, 2-a]pyrazin-3(7H)-ones (Cypridina Luciferin Analogues) (2008)
  • Author(s): Hirano, T, Takahashi, Y., Kondo, H., Maki, S., Kojima, S., Ikeda, H., Niwa, H.
  • Journal Title: Photochem. Photobiol、Sci. 130 Pages: 197-207
  • Description: 「研究成果報告書概要(和文)」より
  • Peer Reviewed
• [Journal Article] The Facile Generation of a Tetramethyleneethane Type Radical Cation and Biradical Utilizing a 3,4-Di(α-styryl)furan and a Photoinduced ET and Back ET Sequence (2008)
  • Author(s): Ikeda, T., Ikeda, H., Takahashi, Y., Yamada, M., Mizuno, K., Tero-Kubota, S., Yamauchi, S.
  • Journal Title: J. Am. Chem. Soc. 130 Pages: 2466-2472
  • Description: 「研究成果報告書概要(欧文)」より
• [Journal Article] The Reaction Mechanism for the High Quantum Yield of th (2008)
  • Author(s): Hirano, T., Takahashi, Y., Kondo, H., Maki, S., Kojima, S., Ikeda, H., Niwa, H.
  • Journal Title: Photochem. Photobiol. Sci. 7 Pages: 197-207
  • Description: 「研究成果報告書概要(欧文)」より
• [Journal Article] Thermoluminescence Originating from the Singlet Excited State of a 1, 4-Diphenvlcyclohexane-l, 4-diyl : A Potentially General Strategy for the Observation of Short-Lived Biradicals (2007)
  • Author(s): Namai, H., Ikeda, H., Hoshi, Y., Mizuno, K.
  • Journal Title: Angew. Chem. Int. Ed. 13 Pages: 9207-9215
  • Description: 「研究成果報告書概要(和文)」より
  • Peer Reviewed
• [Journal Article] Evidence for Significant Through-Space and Through-Bond Electronic Coupling in the 1, 4-Diphenylcyclohexane-1, 4-diyl Radical Cation Gained by Using Absorption Spectroscopy and DFT Calculations (2007)
  • Author(s): Ikeda, H., Hoshi, Y., Namai, H., Tanaka, F., Goodman, J. L., Mizuno, K.
  • Journal Title: Chem. Em : J. 13 Pages: 9207-9215
  • Description: 「研究成果報告書概要(和文)」より
  • Peer Reviewed
• [Journal Article] Thermoluminescence and a New Organic Light-Emitting Diode (OLED)Based on Triplet-Triplet Fluorescence of the Trimethylenemethane (TMM) Biradical (2007)
  • Author(s): Namai, H., Ikeda, H., Hoshi, Y., Kato, N., Morishita, Y., Mizuno, K. .
  • Journal Title: J. Am. Chem. Soc. 129 Pages: 9032-9036
  • Description: 「研究成果報告書概要(和文)」より
  • Peer Reviewed
• [Journal Article] Substituent Effects on the Energies of the Electronic Transitions of Geminally Diphenyl-Substituted Trimethylenemethane (TMM) Radical Cations. Experimental and Theoretical Evidence for a Twisted Molecular and Localized Electronic Structure (2007)
  • Author(s): Namai, H., Ikeda, H., Kato, N., Mizuno, K.
  • Journal Title: J. Phys. Chem. A 111 Pages: 4436-4442
  • Description: 「研究成果報告書概要(和文)」より
  • Peer Reviewed
• [Journal Article] Spectroscopic and Density Functional Theory Studies of the Molecular Geometry and Electronic Structure of Classical and Nonclassical Radical Ions Derived from 7-Benzhydrylidenenorbornene Analogues (2007)
  • Author(s): Namai, H., Ikeda, H., Hirano, T., Ishii, H., Mizuno, K.
  • Journal Title: J. Phys. Chem. A Pages: 7898-7905
  • Description: 「研究成果報告書概要(和文)」より
  • Peer Reviewed
• [Journal Article] Spectroscopic and Density Functional Theory Studies of the Molecular Geometry and Electronic Structure of Classical and Nonclassical Radical Ions Derived from 7-Benzhydrylidenenorbornene Analogues (2007)
  • Author(s): Ikeda, H., Sakai, A., Namai, H., Kawabe, A., Mizuno, K.
  • Journal Title: Tetrahedron Lett. 48 Pages: 8338-8342
  • Description: 「研究成果報告書概要(和文)」より
  • Peer Reviewed
• [Journal Article] Thermoluminescence Originating from the Singlet Excited State of a 1,4-Diphenylcy cIohexane-1,4-diyl : A Potentially General Strateay for the Observation of Short-Lived Biradicals (2007)
  • Author(s): Namai, H., Ikeda, H., Hoshi, Y., Mizuno, K.
  • Journal Title: Angew. Chem. Int. Ed. 46 Pages: 7396-7398
  • Description: 「研究成果報告書概要(欧文)」より
• [Journal Article] Evidence for Significant Through-Space and Through-Bond Electronic Coupling in the 1,4-Diphenylcyclohexane-1,4-diyl Radical Cation Gained by Using Absorption Spectroscopy and DFT Calculations (2007)
  • Author(s): Ikeda, H., Hoshi, Y., Namai, H., Tanaka, F., Goodman, J. L., Mizuno, K.
  • Journal Title: Chem. Eur. J. 13 Pages: 9207-9215
  • Description: 「研究成果報告書概要(欧文)」より
• [Journal Article] Thermoluminescence and a New Organic Light-Emitting Diode (OLED) Based on Triplet-Triplet Fluorescence of the Trimethylenemethane (TMM) Biradical (2007)
  • Author(s): Namai, H., Ikeda, H., Hoshi, Y., Kato, N., Morishita, Y., Mizuno, K.
  • Journal Title: J. Am. Chem. Soc. 129 Pages: 9032-9036
  • Description: 「研究成果報告書概要(欧文)」より
• [Journal Article] Spectroscopic and Density Functional Theory Studies of the Molecular Geometry and Electronic Structure of Classical and Nonclassical Radical Ions Derived from 7-Benzhydrylidenenorbomene Analogues (2007)
  • Author(s): Namai, H., Ikeda, H., Hirano, T., Ishii, H., Mizuno, K.
  • Journal Title: J. Phys. Chem. A 111 Pages: 7898-7905
  • Description: 「研究成果報告書概要(欧文)」より
• [Journal Article] Synthesis, X-ray Crystallographic Analysis, and Theoretical Structure Analysis of Tetrathienylethenes Designed for Photoand Electrochromism (2007)
  • Author(s): Ikeda, H., Sakai, A., Namai, H., Kawabe, A., Mizuno, K.
  • Journal Title: Tetrahedron Lett. 48 Pages: 8338-8342
  • Description: 「研究成果報告書概要(欧文)」より
• [Journal Article] Electron-Transfer Fluorescence Quenching of Aromatic Hydrocarbons by Europium and Ytterbium Ions in Acetonitrile (2006)
  • Author(s): Inada, T., Funasaka, Y., Kikuchi, K., Takahashi, Y., Ikeda, H.
  • Journal Title: J. Phys. Chem. A 110 Pages: 2595-2600
  • Description: 「研究成果報告書概要(和文)」より
  • Peer Reviewed
• [Journal Article] Real Light Emitter in the Bioluminescence of the Calcium-activated Photoproteins Aequorin and Obelin ; Light Emission from the Singlet- excited State of Coelenteramide Phenolate Anion in a Contact Ion Pair (2006)
  • Author(s): Mori, K., Maki, S., Niwa, H., Ikeda, H., Hirano, T.
  • Journal Title: Tetrahedron 62 Pages: 6272-6288
  • Description: 「研究成果報告書概要(和文)」より
  • Peer Reviewed
• [Journal Article] Photoinduced Electron-transfer Systems Consisting of Electron-donating Pyrenes or Anthracenes and Benzimidazolines for Reductive Transformation of Carbonyl Compounds (2006)
  • Author(s): Hasegawa, E., Takizawa, S., Seida, T., Yamaguchi, A., Yamaguchi, N., Chiba, N., Takahashi, T., Ikeda, H., Akiyama, K.
  • Journal Title: Tetrahedron 62 Pages: 6581-6588
  • Description: 「研究成果報告書概要(和文)」より
  • Peer Reviewed
• [Journal Article] Chemiluminescence of 6-Ary1-2-Methylimidazo[1, 2-a]pyrazin-3(7H)-ones in DMSO/TMG and in Diglyme/acetate Buffer : Support for the Chemiexcitation Process to Generate the Singlet-excited State of Neutral Oxyluciferin in a High Quantum Yield in the Cypridina (Vargula) Bioluminescence Mechanism (2006)
  • Author(s): Ikeda, H., Namai, H., Kato, N., Ikeda, T.
  • Journal Title: Tetrahedron Lett. 47 Pages: 1501-1504
  • Description: 「研究成果報告書概要(和文)」より
  • Peer Reviewed
• [Journal Article] Matrix Isolation and DFT CalculatElectron Oxons for the TMM Radical Cation Generated via the Single Electron Oxidation of a Methylenecyclopropane (2006)
  • Author(s): Ikeda, H., Namai, H., Kato, N., Ikeda, T.
  • Journal Title: Tetrahedron, Lett. 47 Pages: 1857-1860
  • Description: 「研究成果報告書概要(和文)」より
  • Peer Reviewed
• [Journal Article] Chemiluminescence of 6-Ary1-2-Methylimidazo[1, 2-a]pyrazin-3(7H)-ones in DMSO/TMG and in Diglyme/acetate Buffer : Support for the Chemiexcitation Process to Generate the Singlet-excited State of Neutral Oxyluciferin in a High Quantum Yield in the Cypridina (Vargula) Bioluminescence Mechanism (2006)
  • Author(s): Takahashi, Y., Kondo, H., Maki, S., Niwa, H., Ikeda, H., Hirano, T.
  • Journal Title: Tetrahedron Lett 47 Pages: 6057-6061
  • Description: 「研究成果報告書概要(和文)」より
  • Peer Reviewed
• [Journal Article] Real Light Emitter in the Bioluminescence of the Calcium-activated Photoproteins Aequorin and Obelin : Light Emission from the Singlet-excited State of Coelenteramide Phenolate Anion in a Contact Ion Pair (2006)
  • Author(s): Mori, K., Maki, S., Niwa, H., Ikeda, H., Hirano, T.
  • Journal Title: Tetrahedron 62 Pages: 6272-6288
  • Description: 「研究成果報告書概要(欧文)」より
• [Journal Article] The First Observation in an Organic Medium and DFT Calculation of the TMM Radical Anion Generated via a Single Electron Reduction of a Methylenecyclopropane (2006)
  • Author(s): Ikeda, H., Namai, H., Kato, N., Ikeda, T.
  • Journal Title: Tetrahedron Lett. 47 Pages: 1501-1504
  • Description: 「研究成果報告書概要(欧文)」より
• [Journal Article] Matrix Isolation and DFT Calculations for the TMM Radical Cation Generated via the Single Electron Oxidation of a Methylenecyclopropane (2006)
  • Author(s): Ikeda, H., Namai, H., Kato, N., Ikeda, T.
  • Journal Title: Tetrahedron Lett. 47 Pages: 1857-1860
  • Description: 「研究成果報告書概要(欧文)」より
• [Journal Article] Chemiluminescence of 6-Ary1-2-Methylimidazo[l, 2-a]-pyrazin-3(7H)-ones in DMSO/TMG and in Diglyme/acetate Buffer : Support for the Chemiexcitation Process to Generate the Singlet-excited State of Neutral Oxyluciferin in a High Quantum Yield in the Cypridina (Vargula) Bioluminescence Mechanism (2006)
  • Author(s): Takahashi, Y., Kondo, H., Maki, S., Niwa, H., Ikeda, H., Hirano, T.
  • Journal Title: Tetrahedron Lett. 47 Pages: 6057-6061
  • Description: 「研究成果報告書概要(欧文)」より
• [Journal Article] Divergent Oxidative Rearrangements in Solution and in a Zeolite : Distal vs Proximal Bond Cleavage of Methylenecyclopropanes (2005)
  • Author(s): Ikeda, H., Nomura, T., Akiyama, K., Oshima, M., Roth, H. D., Tero-Kubota, S., Miyashi, T.
  • Journal Title: J. Am. Chem. Soc. 127 Pages: 14497-14504
  • Description: 「研究成果報告書概要(和文)」より
  • Peer Reviewed
• [Journal Article] An Evolved Explanation for the Molecular Geometry and Electronic Structure of Diphenyl-substituted Cyclic Trimethylenemethane (TMM) : a Nearly Planar Conformation with a Considerably Localized Electronic State (2005)
  • Author(s): Ikeda, H., Namai, H., Taki, H., Miyashi, T.
  • Journal Title: J. Org. Chem. 70 Pages: 3806-3813
  • Description: 「研究成果報告書概要(和文)」より
  • Peer Reviewed
• [Journal Article] Contrastive Photoreduction Pathways of Benzophenones Governed by Regiospecific Deprotonation oflmidazoline Radical Cations and Additive Effects (2005)
  • Author(s): Hasegawa, E., Seida, T., Chiba, N., Takahashi, T., Ikeda, H.
  • Journal Title: J. Org. Chem. 70 Pages: 9632-9635
  • Description: 「研究成果報告書概要(和文)」より
  • Peer Reviewed
• [Journal Article] Incorporation of 2-Arylhexa-1, 5-diene into Pentasil Zeolite : A Distorted 1-Arylcyclohexane-1, 4-divl Radical Cation at Room Temperature (2005)
  • Author(s): Ikeda, H., Minegishi, T., Miyashi, T., Lakkaraju, P. S., Sauers, R. R., Roth, H. D.
  • Journal Title: J. Phys. Chem. B 109 Pages: 2504-2511
  • Description: 「研究成果報告書概要(和文)」より
  • Peer Reviewed
• [Journal Article] Substituent Effects on the Spectroscopic Properties of Solvatochromic 2-Phenylimidazo[1, 2-a]pyrazin-3(7H)-ones : An Effective Control for the Colorimetric Sensor Properties (2005)
  • Author(s): Takamuki, Y., Maki, S., Niwa, H., Ikeda, H., Hirano, T.
  • Journal Title: Tetrahedron 46 Pages: 10073-10080
  • Description: 「研究成果報告書概要(和文)」より
  • Peer Reviewed
• [Journal Article] Direct Observation and Kinetic Characterization of 0-Quinodimethane and Its Radical Cation Variant Generated in a Photoinduced Electron-transfer Reaction of 1, 2-Bis(α-styryl)benzene (2005)
  • Author(s): Ikeda, H., Ikeda, T., Akagi, M., Namai, H., Miyashi, T., Takahashi, Y., Kamata, M.
  • Journal Title: Tetrahedron Lett. 46 Pages: 1831-1835
  • Description: 「研究成果報告書概要(和文)」より
  • Peer Reviewed
• [Journal Article] Chemical Capture of an Unprecedented Oxatetramethyleneethane Radical Cation with a Through-space Electronic Coupling (2005)
  • Author(s): Ikeda, H., Tanaka, F., Kabuto, C.
  • Journal Title: Tetrahedron Lett. 46 Pages: 2663-2667
  • Description: 「研究成果報告書概要(和文)」より
  • Peer Reviewed
• [Journal Article] Significant Solvent Effects and Unusual Additions of p-Chloranil in the Photoinduced Electron-transfer Reaction of 2, 2-Dianisvl-4-isonropylidene-3, 3-dimethylcyclobutanone (2005)
  • Author(s): Ikeda, H., Tanaka, F., Kabuto, C.
  • Journal Title: Tetrahedron Lett. 46 Pages: 3863-3867
  • Description: 「研究成果報告書概要(和文)」より
  • Peer Reviewed
• [Journal Article] Spectroscopic and DFT Evidence for a Nonclassical Radical Cation Derived from 7-Benzhvdrvlidenenorbornene (2005)
  • Author(s): Ikeda, H., Namai, H., Hirano, T.
  • Journal Title: Tetrahedron Lett. 46 Pages: 3917-3921
  • Description: 「研究成果報告書概要(和文)」より
  • Peer Reviewed
• [Journal Article] Spectroscopic and DFT Studies of Nonclassical and Classical Radical Cations of 7-Benzhydrylidenenorbomene Analogues : Contrasting Molecular Geometry and Electronic Structures Originating from the Different Patterns of Electronic Coupling (2005)
  • Author(s): Ikeda, H., Namai, H., Hirano, T.
  • Journal Title: Tetrahedron Lett. 46 Pages: 7631-7635
  • Description: 「研究成果報告書概要(和文)」より
  • Peer Reviewed
• [Journal Article] Substituent Effects on the Kinetics for the Chemiluminescence Reaction of 6-Arylimidazo[1, 2-α]pyrazin-3(7H)-ones(Cypridina luciferin analogues) : Support for the Single Electron Transfer (SET)-Oxygenation Mechanism with Triplet Molecular Oxygen (2005)
  • Author(s): Kondo, H., Igarashi, T., Maki, S., Niwa, H., Ikeda, H., Hirano, T.
  • Journal Title: Tetrahedron Lett. 46 Pages: 7701-7704
  • Description: 「研究成果報告書概要(和文)」より
  • Peer Reviewed
• [Journal Article] Contrastive Photoreduction Pathways of Benzophenones Governed by Regiospecific Deprotonation of Imidazoline Radical Cations and Additive Effects (2005)
  • Author(s): Hasegawa, E., Seida, T., Chiba, N., Takahashi, T., Ikeda, H.
  • Journal Title: J. Org. Chem. 70 Pages: 9632-9635
  • Description: 「研究成果報告書概要(欧文)」より
• [Journal Article] Incorporation of 2-Arylhexa-1,5-diene into Pentasil Zeolite : A Distorted 1-AryIcyclohexane-1,4-diyl Radical Cation at Room Temperature (2005)
  • Author(s): Ikeda, H., Minegishi, T., Miyashi, T., Lakkaraju, P. S., Sauers, R. R., Roth, H. D.
  • Journal Title: J. Phys. Chem. B 109 Pages: 2504-2511
  • Description: 「研究成果報告書概要(欧文)」より
• [Journal Article] Substituent Effects on the Spectroscopic Properties of Solvatochromic 2-Phenylimidazo[l, 2-a]pyrazin-3(7H)-ones : An Effective Control for the Colorimetric Sensor Properties (2005)
  • Author(s): Takamuki, Y., Maki, S., Niwa, H., Ikeda, H., Hirano, T.
  • Journal Title: Tetrahedron 61 Pages: 10073-10080
  • Description: 「研究成果報告書概要(欧文)」より
• [Journal Article] Direct Observation and Kinetic Characterization of o-Quinodimethane and Its Radical Cation Variant Generated in a Photoinduced Electron-transfer Reaction of 1,2-Bis( α -styryl)benzene (2005)
  • Author(s): Ikeda, H., Ikeda, T., Akagi, M., Namai, H., Miyashi, T., Takahashi, Y., Kamata, M.
  • Journal Title: Tetrahedron Lett. 46 Pages: 1831-1835
  • Description: 「研究成果報告書概要(欧文)」より
• [Journal Article] Significant Solvent Effects and Unusual Additions of p-Chloranil in the Photoinduced Electron-transfer Reaction of 2,2-Dianisyl-4-isopropylidene-3,3-dimethylcyclobutanone (2005)
  • Author(s): Ikeda, H., Tanaka, F., Kabuto, C.
  • Journal Title: Tetrahedron Lett. 46 Pages: 3863-3866
  • Description: 「研究成果報告書概要(欧文)」より
• [Journal Article] Spectroscopic and DFT Evidence for a Nonclassical Radical Cation Derived from 7-Benzhydrylidenenorbornene (2005)
  • Author(s): Ikeda, H., Namai, H., Hirano, T.
  • Journal Title: Tetrahedron Lett. 46 Pages: 3917-3921
  • Description: 「研究成果報告書概要(欧文)」より
• [Journal Article] Spectroscopic and DFT Studies of Nonclassical and Classical Radical Cations of 7-Benzhydrylidenenorbornene Analogues : Contrasting Molecular Geometry and Electronic Structures Originating from the Different Patterns of Electronic Coupling (2005)
  • Author(s): Ikeda, H., Namai, H., Hirano, T.
  • Journal Title: Tetrahedron Lett. 46 Pages: 7631-7635
  • Description: 「研究成果報告書概要(欧文)」より
• [Journal Article] Substituent Effects on the Kinetics for the Chemiluminescence Reaction of 6-Arylimidazo[l, 2-a]pyrazin-3(7H)-ones (Cypridinaluciferin analogues) : Support for the Single Electron Transfer (SET)-Oxygenation Mechanism with Triplet Molecular Oxygen (2005)
  • Author(s): Kondo, H., Igarashi, T., Maki, S., Niwa, H., Ikeda, H., Hirano, T.
  • Journal Title: Tetrahedron Lett. 46 Pages: 7701-7704
  • Description: 「研究成果報告書概要(欧文)」より
• [Journal Article] Substituent Effects on the Solvatochromism of 2-Phenylimidazopyrazinones : Effective Control of the Color Variation Range and Sensitivity toward Indication of the Proton Donor Ability of Solvents by an Electron-withdrawing Group Substitution (2004)
  • Author(s): Takamuki, Y., Maki, S., Niwa, H., Ikeda, H., Hirano, T.
  • Journal Title: Chem. Lett. Pages: 1484-1485
  • Description: 「研究成果報告書概要(和文)」より
  • Peer Reviewed
• [Journal Article] Photoinduced Electron-transfer, Pyrolyses, and Direct Irradiation Reactions of 2-Methylenecyclobutanones : Regioselective Bond Cleavage Depends on the Substituents and Method of Activation (2004)
  • Author(s): Ikeda, H., Tanaka, F., Miyashi, T., Akiyama, K., Tero-Kubota, S.
  • Journal Title: Eur. J. Org. Chem. 2004 Pages: 1500-1508
  • Description: 「研究成果報告書概要(和文)」より
  • Peer Reviewed
• [Journal Article] Rearrangement of a 2-Methylenecyclobutan-1-one Derivative Triggered by Photoinduced Electron Transfer : An Unprecedented Oxa Analogue of the Tetramethyleneethane Radical Cation (2004)
  • Author(s): Ikeda, H., Tanaka, F., Akiyama, K., Tero-Kubota. S., Miyashi, T.
  • Journal Title: J、Am. Chem. Soc. 126 Pages: 414-415
  • Description: 「研究成果報告書概要(和文)」より
  • Peer Reviewed
• [Journal Article] Photoinduced Electron-transfer Bicyclopropenyl-benzene Rearrangements of 2, 2', 3, 3'-TetraphenY】bicvclopropenvls : A New Mechanism via Dewar Benzene (2004)
  • Author(s): Ikeda, H., Hoshi, Y., Kikuchi, Y., Tanaka, F., Miyashi, T.
  • Journal Title: Org. Lett. 6 Pages: 1029-1032
  • Description: 「研究成果報告書概要(和文)」より
  • Peer Reviewed
• [Journal Article] Metal-ion Complexation of Imidazo[1, 2-a]pyrazin-3(7H)-ones : Continuous Changes in Absorption Spectra of Complexes Depending on the Lewis Acidity of the Metal Ion (2004)
  • Author(s): Sekiguchi, T., Maki, S., Niwa, H., Ikeda, H., Hirano, T.
  • Journal Title: Tetrahedron Lett. 45 Pages: 1065-1069
  • Description: 「研究成果報告書概要(和文)」より
  • Peer Reviewed
• [Journal Article] Regioselective Phenyl-substitution Effects on the Solvatochromism of 2-Phenylimidazo[1, 2-a]pyrazin-3(7H)-one Derivatives : Expansion of the Color Variation Range of a Visible Indicator for the Proton Donor Ability of Solvents (2004)
  • Author(s): Fujio, S., Hashizume, D., Takamuki, Y., Yasui, M., Iwasaki, F., Maki, S., Niwa, H., Ikeda, H., Hirano, T.
  • Journal Title: Tetrahedron Lett. 45 Pages: 8531-8534
  • Description: 「研究成果報告書概要(和文)」より
  • Peer Reviewed
• [Journal Article] Rearrangement of a 2-Methylenecyclobutan-1-one Derivative Triggered by Photoinduced Electron Transfer : An Unprecedented Oxa Analogue of the Tetramethyleneethane Radical Cation (2004)
  • Author(s): Ikeda, H., Tanaka, F., Akiyama, K., Tero-Kubota, S., Miyashi, T.
  • Journal Title: J. Am. Chem. Soc. 126 Pages: 414-415
  • Description: 「研究成果報告書概要(欧文)」より
• [Journal Article] Photoinduced Electron-transfer Bicyclopropenyl-benzene Rearrangements of 2,2', 3,3'-Tetraphenylbicyclopropenyls : A New Mechanism via Dewar Benzene (2004)
  • Author(s): Ikeda, H., Hoshi, Y., Kikuchi, Y., Tanaka, F., Miyashi, T.
  • Journal Title: Org. Lett 6 Pages: 1029-1032
  • Description: 「研究成果報告書概要(欧文)」より
• [Journal Article] Metal-ion Complexation of Imidazo[l, 2-a]pyrazin-3(7H)-ones : Continuous Changes in Absorption Spectra of Complexes Depending on the Lewis Acidity of the Metal Ion (2004)
  • Author(s): Sekiguchi, T., Maki, S., Niwa, H., Ikeda, H., Hirano, T.
  • Journal Title: Tetrahedron Lett. 45 Pages: 1065-1069
  • Description: 「研究成果報告書概要(欧文)」より
• [Journal Article] Regioselective Phenyl-substitution Effects on the Solvatochromism of 2-Phenylimidazo[l, 2-a]pyrazin-3(7H)-one Derivatives : Expansion of the Color Variation Range of a Visible Indicator for the Proton Donor Ability of Solvents (2004)
  • Author(s): Fujio, S., Hashizume, D., Takamuki, Y., Yasui, M., Iwasaki, F., Maki, S., Niwa, H., Ikeda, H., Hirano, T.
  • Journal Title: Tetrahedron Lett. 45 Pages: 8531-8534
  • Description: 「研究成果報告書概要(欧文)」より
• [Journal Article] Spectroscopic and Calorimetric Studies on the Mechanism of Methylenecyclopropane Rearrangements Triggered by Photoinduced Electron Transfer (2003)
  • Author(s): Ikeda, H., Akiyama, K., Takahashi, Y., Nakamura, T., Ishizaki, S., Shiratori, Y., Ohaku, H., Goodman, J. L., Houmam, A., Wayner, D. D. M., Tero-Kubota, S., Miyashi, T.
  • Journal Title: J. Am. Chem. Soc. 125 Pages: 9147-9157
  • Description: 「研究成果報告書概要(和文)」より
  • Peer Reviewed
• [Journal Article] Electron-Transfer (ET)Fluorescence Quenching in Benzonitrile. Evidence of an Intermolecular ET with △G < -0.5 eV being a Diffusion-Controlled Process (2002)
  • Author(s): Inada, T., Kikuchi, K., Takahashi, Y., Ikeda, H, Miyashi, T.
  • Journal Title: J. Phys. Chem. A 106 Pages: 4345-4349
  • Description: 「研究成果報告書概要(和文)」より
  • Peer Reviewed
• [Journal Article] Electron-Transfer (ET) Fluorescence Quenching in Benzonitrile. Evidence of an Intermolecular ET with Δ G < -0.5 eV being a Diffusion-Controlled Process (2002)
  • Author(s): Inada, T, Kikuchi, K., Takahashi, Y., Ikeda, H., Miyashi, T.
  • Journal Title: J. Phys. Chem. A 106 Pages: 4345-4349
  • Description: 「研究成果報告書概要(欧文)」より
• [Journal Article] Photosensitized Electron-transfer Reactions of 1-Isopropylidene-2-methylene-3, 3-diphenylcyclobutane-[4+4] Cycloaddition and Cyclodimerization Initiated by a Buta-l, 3-diene Radical Cation Functionality (2001)
  • Author(s): Ikeda, H., Aburakawa, N., Tanaka, F, Fukushima, T., Miyashi, T.
  • Journal Title: Eur. J. Org. Chem. 2001 Pages: 3445-3452
  • Description: 「研究成果報告書概要(和文)」より
  • Peer Reviewed
• [Journal Article] l, 3-Bis(4-methoxyphenyl)cyclohexane-1, 3-diy1 Cation Radical : Change of Reactivity Depending upon One-Electron Oxidation Conditions (2001)
  • Author(s): Ikeda, H., Hoshi, Y., Miyashi, T.
  • Journal Title: Tetrahedron Lett. 42 Pages: 8485-8488
  • Description: 「研究成果報告書概要(和文)」より
  • Peer Reviewed
• [Journal Article] Photosensitized Electron-transfer Reactions of 1-Isopropylidene-2-methylene-3,3-diphenylcyclobutane - [4 + 4] Cycloaddition and Cyclodimerization Initiated by a Buta-1,3-diene Radical Cation Functionality (2001)
  • Author(s): Ikeda, H., Aburakawa, N., Tanaka, F., Fukushima, T., Miyashi, T.
  • Journal Title: Eur. J. Org. Chem. 2001 Pages: 3445-3452
  • Description: 「研究成果報告書概要(欧文)」より
• [Journal Article] 1,3-Bis(4-methoxyphenyl)cyclohexane-1,3-diyl Cation Radical : Change of Reactivity Depending up on One-Electron Oxidation Conditions (2001)
  • Author(s): Ikeda, H., Hoshi, Y., Miyashi, T.
  • Journal Title: Tetrahedron Lett. 42 Pages: 8485-8488
  • Description: 「研究成果報告書概要(欧文)」より
• [Presentation] Thermoluminescence from Reactive Biradical Intermediates (2007)
  • Author(s): Ikeda, H., Namai, H., Mizuno, K. (Invited Lecture)
  • Organizer: 2007 Korea-Japan Symposium on Frontier Photoscience
  • Place of Presentation: 韓国・慶州
  • Year and Date: 20071122-20071125
  • Description: 「研究成果報告書概要(和文)」より
• [Presentation] Thermoluminescence from Reactive Biradical Intermediates (2007)
  • Author(s): Ikeda, H., Namai, H., Mizuno, K. (Invited Lecture)
  • Organizer: 2007 Korea-Japan Symposium on Frontier Photoscience
  • Place of Presentation: Gyeonjyu, Korea
  • Year and Date: 20071122-20071125
  • Description: 「研究成果報告書概要(欧文)」より
• [Presentation] A Mechanistic Connection between Photoinduced Electron-transfer Reactions and Thermoluminescence of Methylenecyclopropanes (2006)
  • Author(s): Ikeda, H., Namai, H., Kato, N., Mizuno, K. (Invited Lecture)
  • Organizer: 2006 Korea-Japan Symposium on Frontier Photoscience
  • Place of Presentation: 韓国・ソウル
  • Year and Date: 20061103-20061105
  • Description: 「研究成果報告書概要(和文)」より
• [Presentation] A Mechanist (2006)
  • Author(s): Ikeda, H., Namai, H., Kato, N., Mizuno, K. (Invited Lecture)
  • Organizer: A Mechanistic Connection between Photoinduced Electron-transfer Reactions and Thermoluminescence of Methylenecyclopropanes
  • Place of Presentation: Soul, Korea
  • Year and Date: 20061103-20061105
  • Description: 「研究成果報告書概要(欧文)」より
• [Presentation] Mechanistic Connection of Photoinduced Electron-transfer Reaction and Thennoluminescence of Methylenecyclopropanes (2006)
  • Author(s): Ikeda, H., Namai, H., Kato, N.
  • Organizer: XXI IUPAC Symposium on Photochemistry
  • Place of Presentation: 京都・京都
  • Year and Date: 20060402-20060407
  • Description: 「研究成果報告書概要(和文)」より
• [Presentation] Mechanistic Connection of Photoinduced Electron-transfer Reaction and Thermoluminescence of Methylenecyclopropanes (2006)
  • Author(s): Ikeda, H., Namai, H., Kato, N.
  • Organizer: XXI IUPAC Symposium on Photochemistry
  • Place of Presentation: Kyoto, Kyoto
  • Year and Date: 20060402-20060407
  • Description: 「研究成果報告書概要(欧文)」より
• [Presentation] An OLED-oriented Study on Thermoluminescence of Arylated Methylenecyclopropane (2006)
  • Author(s): Ikeda, H., Namai, H., Kato, N., Mizuno, K. (Invited Lecture)
  • Organizer: International Workshop of Molecular Function in Kansai
  • Place of Presentation: 大阪・大阪
  • Year and Date: 2006-11-13
  • Description: 「研究成果報告書概要(和文)」より
• [Presentation] An OLED-oriented Study on Thermoluminescence of Arylated Methylenecyclopropane (2006)
  • Author(s): Ikeda, H., Namai, H., Kato, N., Mizuno, K. (Invited Lecture)
  • Organizer: International Workshop of Molecular Function in Kansai
  • Place of Presentation: Osaka, Japan
  • Year and Date: 2006-11-13
  • Description: 「研究成果報告書概要(欧文)」より
• [Presentation] Electron-transfer Reactions of Methylenecyclopropanes. Basics and Applications (2005)
  • Author(s): Ikeda, H., Namai, H., Hoshi, Y, Kato, N., Morishita, Y. (Invited, Plenary Lecture)
  • Organizer: 2005 International Chemical Congress of Pacific Basin Societies
  • Place of Presentation: 米国・ホノルル
  • Year and Date: 20051216-20051221
  • Description: 「研究成果報告書概要(和文)」より
• [Presentation] Electron-transfer Reactions of Methylenecyclopropanes. Basics and Applications (2005)
  • Author(s): Ikeda, H., Namai, H., Hoshi, Y., Kato, N., Morishita, Y. (Invited and Plenary Lecture)
  • Organizer: 2005 International Chemical Congress of Pacific Basin Societies
  • Place of Presentation: Honolulu, USA
  • Year and Date: 20051216-20051221
  • Description: 「研究成果報告書概要(欧文)」より
• [Presentation] Regioselective Bond Cleavage of Methylenecyclopropanes upon Electron-Transfer in Solution and Incorporation into a Zeolite (2005)
  • Author(s): Ikeda, H., Nomura, T., Oshima, M., Ueda, M., Miyashi, T., Akiyama, K., Tero-Kubota, S., Roth, H. D. (Invited Lecture)
  • Organizer: Chemistry, Biology, and Material Science towards Creating New Science and Industry based on Inter-Nanoscience
  • Place of Presentation: 大阪・大阪
  • Year and Date: 20050222-20050223
  • Description: 「研究成果報告書概要(和文)」より
• [Presentation] Regioselective Bond Cleavage of Methylenecyclopropanes upon Electron-Transfer in Solution and Incorporation intoa Zeolite (2005)
  • Author(s): Ikeda, H., Nomura, T., Oshima, M., Ueda, M., Miyashi, T., Akiyama, K., Tero-Kubota, S., Roth, H. D. (Invited Lecture)
  • Organizer: Chemistry, Biology, and Material Science towards Creating New Science and Industry based on Inter-Nanoscience
  • Place of Presentation: Osaka, Osaka, Japan
  • Year and Date: 20050222-20050223
  • Description: 「研究成果報告書概要(欧文)」より
• [Presentation] Divergent Reactions of Methylenecyclopropanes upon Electron-Transfer in Solution and Incorporation into 1 Zeolite : Distal vs. Proximal Bond Cleavage (2004)
  • Author(s): Ikeda, H., Nomura, T., Oshima, M., Ueda, M., Miyashi, T., Akiyama, K., Tero-Kubota, S., Roth, H. D. (Invited Lecture)
  • Organizer: 2004 Korea-Japan Symposium on Frontier Photoscience
  • Place of Presentation: 韓国・太田
  • Year and Date: 20041120-20041123
  • Description: 「研究成果報告書概要(和文)」より
• [Presentation] Divergent Reactions of Methylenecyclopropanes upon Electron-Transfer in Solution and Incorporation into a Zeolite : Distal vs. Proximal Bond Cleavage (2004)
  • Author(s): Ikeda, H., Nomura, T., Oshima, M., Ueda, M., Miyashi, T., Akiyama, K., Tero-Kubota, S., Roth, H. D. (Invited Lecture)
  • Organizer: 2004 Korea-Japan Symposium on Frontier Photoscience
  • Place of Presentation: Daeieon, Korea
  • Year and Date: 20041120-20041123
  • Description: 「研究成果報告書概要(欧文)」より
• [Presentation] Contrasting Electron-Transfer Reactions of Methylenecyclopropanes using a Photosensitizer and a Zeolite (2004)
  • Author(s): Ikeda, H., Nomura, T., Miyashi, T., Akiyama, K., Tero-Kubota, S., Roth, H. D.
  • Organizer: XX IUPAC Symposium on Photochemisfry
  • Place of Presentation: スペイン・グラナダ
  • Year and Date: 20040717-20040722
  • Description: 「研究成果報告書概要(和文)」より
• [Presentation] Contrasting Electron-Transfer Reactions of Methylenecyclopropanes using a Photosensitizer and a Zeolite (2004)
  • Author(s): Ikeda, H., Nomura, T., Ueda, M., Miyashi, T., Akiyama, K., Tero-Kubota, S., Roth, H. D. (Invited Lecture)
  • Organizer: CREST International Symposium on Radical Ion Reactivity
  • Place of Presentation: Hyogo, Japan
  • Year and Date: 20040620-20060624
  • Description: 「研究成果報告書概要(欧文)」より
• [Presentation] Contrasting Electron-Transfer Reactions of Methylenecyclopropanesusing a Photosensitizer and a Zeolite (2004)
  • Author(s): Ikeda, H., Nomura, T., Ueda, M., Miyashi, T., Akiyama, K., Tero-Kubota, S., Roth, H. D. (Invited Lecture)
  • Organizer: CREST International Symposium on Radical Ion Reactivity
  • Place of Presentation: 兵庫・淡路
  • Year and Date: 20040620-20040624
  • Description: 「研究成果報告書概要(和文)」より
• [Presentation] Contrasting Electron-Transfer Reactions of Methylenecyclopropanes using a Photosensitizer and a Zeolite (2004)
  • Author(s): Ikeda, H., Nomura, T., Miyashi, T., Akiyama. K., Tero-Kubota, S., Roth, H. D
  • Organizer: XX IUPAC Symposium on Photochemistry
  • Place of Presentation: Granada, Spain
  • Year and Date: 20040617-20040622
  • Description: 「研究成果報告書概要(欧文)」より
• [Presentation] Electron-Transfer Reactions of 1,4-Diarylbicyclo[2.2.0]hexane Derivatives (2004)
  • Author(s): Ikeda, H. (Invited Lecture)
  • Organizer: Organic Seminar at Universidad Politcnica de Valencia
  • Place of Presentation: スペイン・バレンシア
  • Year and Date: 2004-07-24
  • Description: 「研究成果報告書概要(和文)」より
• [Presentation] Electron-Transfer Reactions of 1,4-Diarylbicyclo[2.2.0]hexane Derivatives (2004)
  • Author(s): Ikeda, H. (Invited Lecture)
  • Organizer: Organic Seminar at Universidad Politcnica de Valencia
  • Place of Presentation: Valencia, Spain
  • Year and Date: 2004-07-24
  • Description: 「研究成果報告書概要(欧文)」より
• [Book] 光化学(ビラジカルを経由する光誘起電子移動反応, 熱発光, そして有機EL) (2008)
  • Author(s): 池田 浩(分担執筆)
  • Total Pages: 5
  • Publisher: 光化学協会
  • Description: 「研究成果報告書概要(和文)」より
• [Book] 化学工業(光およびゼオライト誘起による対照的な有機電子移動反応-ゼオライト表面の新しい有機修飾のための基礎研究-) (2007)
  • Author(s): 池田 浩
  • Total Pages: 5
  • Publisher: 化学工業社
  • Description: 「研究成果報告書概要(和文)」より
• [Book] 光応用技術・材料事典(第1章, 第一節) (2006)
  • Author(s): 池田 浩(分担執筆)
  • Total Pages: 3
  • Publisher: (株)産業技術サービスセンター
  • Description: 「研究成果報告書概要(和文)」より
• [Patent(Industrial Property Rights)] 化学構造が変化する発光単位を有するポリマー, 及びこれを用いた有機エレクトロルミネセンス素子 (2005)
  • Inventor(s): 池田浩, 他6人.
  • Industrial Property Rights Holder: 日立化成工業株式会社
  • Industrial Property Number: 特許権特願2005-67216特開2006-249229
  • Filing Date: 2005-03-10
  • Description: 「研究成果報告書概要(和文)」より
• [Patent(Industrial Property Rights)] 発光システム, 発光方法及び発光用化学物質 (2004)
  • Inventor(s): 池田浩, 他6人.
  • Industrial Property Rights Holder: 日立化成工業株式会社
  • Industrial Property Number: 特許権PCT/JP2004/019252W02005/062677(PCT出願)
  • Filing Date: 20041222-20031222
  • Description: 「研究成果報告書概要(和文)」より