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Excited Charge Transfer Complex : Effect of Irradiation Wavelength on Asymmetric Photochemistry

Research Project

Project/Area Number 21750044
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Organic chemistry
Research InstitutionOsaka University

Principal Investigator

MORI Tadashi  Osaka University, 工学研究科, 准教授 (70311769)

Project Period (FY) 2009 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Fiscal Year 2010: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Fiscal Year 2009: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Keywords励起波長効果 / エキシプレックス / 温度効果 / 不斉光反応 / 励起CT錯体 / Paterno-Buchi反応 / エントロピー・エンタルピー
Research Abstract

Effect of excitation wavelength on the asymmetric photoreaction of some donor-acceptor complexes has been studied. The diastereoselectivitives observed upon selective excitation at the charge transfer (CT) band are different from those obtained with direct excitation of donor or acceptor molecule. It turned out that both the ground and excited states' interactions are crucial for controlling stereochemical outcomes

Report

(3 results)
  • 2010 Annual Research Report   Final Research Report ( PDF )
  • 2009 Annual Research Report
  • Research Products

    (47 results)

All 2011 2010 2009 Other

All Journal Article (30 results) (of which Peer Reviewed: 30 results) Presentation (13 results) Book (1 results) Remarks (3 results)

  • [Journal Article] Diastereodifferentiating the [2+2] Photocycloaddition of Ethylene to Aryl- menthyl Cyclohexenonecarboxylates : Stacking-Driven Enhancement of the Product Diastereoselectivity That Is Correlated with the Reactant Ellipticity.2010

    • Author(s)
      Tsutsumi, K., Yanagisawa, Y., Furutani, A., Morimoto, T., Kakiuchi, K., Wada, T., Mori, T., Inoue, Y.
    • Journal Title

      Chem.Eur.J. 16(25)

      Pages: 7448-7455

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Conformation Elucidation of Tethered Donor-Acceptor Binaphthyls from the Anisotropy Factor of a Charge-Transfer Band.2010

    • Author(s)
      Nishizaka, M., Mori, T., Inoue, Y.
    • Journal Title

      J.Phys.Chem.Lett. 1(15)

      Pages: 2402-2405

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Experimental and Theoretical Studies on the Chiroptical Properties of Donor-Acceptor Binaphthyls. Effects of Dynamic Conformer Population on Circular Dichroism.2010

    • Author(s)
      Nishizaka, M., Mori, T., Inoue, Y.
    • Journal Title

      J.Phys.Chem.Lett. 1(12)

      Pages: 1809-1812

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Solvent and Temperature Effects on Diastereodifferentiating Paterno-Buchi Reaction of Chiral Alkyl Cyanobenzoates with Diphenylethene upon Direct versus Charge-Transfer Excitation.2010

    • Author(s)
      Matsumura, K., Mori, T., Inoue, Y.
    • Journal Title

      J.Org.Chem. 75(16)

      Pages: 5461-5469

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Critical stereocontrol by inter-amino distance of supramolecular photocyclodimerization of 2-anthracenecarboxylate mediated by 6-(ω-aminoalkylamino)-γ-cyclodextrins.2010

    • Author(s)
      Ke, C., Yang, C., Liang, W., Mori, T., Liu, Y., Inoue, Y.
    • Journal Title

      New J.Chem. 234(7)

      Pages: 1323-1329

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Circular dichroism of donor-acceptor cyclophanes : (4Rp;12Rp)- and (4Sp;12Rp)-12, 15-dimethoxy [2.2] paracyclophane-4, 7-dicarb oxylic acid derivatives.2010

    • Author(s)
      Furo, T., Mori, T., Inoue, Y.
    • Journal Title

      Chirality 22(1E)

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Dual Chiral, Dual Supramolecular Diastereodifferentiating Photocyclodimerization of 2-Anthracenecarboxylate Tethered to Amylose Scaffold.2010

    • Author(s)
      Fukuhara, G., Nakamura, T., Yang, C., Mori, T., Inoue, Y.
    • Journal Title

      Org.Lett. 12(15)

      Pages: 3510-3513

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Diastereodifferentiating Photocyclodimerization of 2-Anthracenecarboxylate Tethered to Cellulose Scaffold.2010

    • Author(s)
      Fukuhara, G., Nakamura, T., Yang, C., Mori, T., Inoue, Y.
    • Journal Title

      J.Org.Chem. 75(12)

      Pages: 4307-4310

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Bio-supramolecular photochirogenesis with molecular chaperone : enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate mediated by prefoldin.2010

    • Author(s)
      Bando, K., Zako, T., Sakono, M., Maeda, M., Wada, T., Nishijima, M., Fukuhara, G., Yang, C., Mori, T., Pace, T.C.S., Bohne, C., Inoue, Y.
    • Journal Title

      Photochem. Photobiol. Sci. 9(5)

      Pages: 655-660

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Solvent and Temperature Effects on Diastereodifferentiating Paterno-Buchi Reaction of Chiral Alkyl Cyanobenzoates with Diphenylethene upon Direct versus Charge-Transfer Excitation.2010

    • Author(s)
      Matsumura, K.; Mori, T.; Inoue, Y.
    • Journal Title

      Journal of Organic Chemistry [Featured Article]

      Volume: 75 Pages: 5461-5469

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Conformation Elucidation of Tethered Donor-Acceptor Binaphthyls from the Anisotropy Factor of a Charge-Transfer Band.2010

    • Author(s)
      Nishizaka, M.; Mori, T.; Inoue, Y.
    • Journal Title

      Journal of Physical Chemistry Letters

      Volume: 1 Pages: 2402-2405

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Experimental and Theoretical Studies on the Chiroptical Properties of Donor-Acceptor Binaphthyls.Effects of Dynamic Conformer Population on Circular Dichroism.2010

    • Author(s)
      Nishizaka, M.; Mori, T.; Inoue, Y.
    • Journal Title

      Journal of Physical Chemistry Letters

      Volume: 1 Pages: 1809-1812

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Diastereodifferentiating the [2+2] Photocycloaddition of Ethylene to Arylmenthyl Cyclohexenonecarboxylates : Stacking-Driven Enhancement of the Product Diaster eoselectivity That Is Correlated with the Reactant Ellipticity.2010

    • Author(s)
      Tsutsumi, K.; Yanagisawa, Y.; Furutani, A.; Morimoto, T.; Kakiuchi, K.; Wada, T.; Mori, T.; Inoue, Y.
    • Journal Title

      Chemistry-A European Journal

      Volume: 16 Pages: 7448-7455

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Critical stereocontrol by inter-amino distance of supramolecular photocyclodime rization of 2-anthracenecarboxylate mediated by 6-(ω-aminoalkylamino)-γ-cyclo dextrins.2010

    • Author(s)
      Ke, C.; Yang, C.; Liang, W.; Mori, T.; Liu, Y.; Inoue, Y.
    • Journal Title

      New Journal of Chemistry

      Volume: 34 Pages: 1323-1329

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Circular dichroism of donor-acceptor cyclophanes : (4Rp;12Rp)- and (4Sp;12Rp)-12,15-dimethoxy[2.2]paracyclophane-4,7-dicarboxylic acid derivatives.2010

    • Author(s)
      Furo, T.; Mori, T.; Inoue, Y.
    • Journal Title

      Chirality

      Volume: 22

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Dual Chiral, Dual Supramolecular Diastereodifferentiating Photocyclodimerization of 2-Anthracenecarboxylate Tethered to Amylose Scaffold.2010

    • Author(s)
      Fukuhara, G.; Nakamura, T.; Yang, C.; Mori, T.; Inoue, Y.
    • Journal Title

      Organic Letters

      Volume: 12 Pages: 3510-3513

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Diastereodifferentiating Photocyclodimerization of 2-Anthracenecarboxylate Tethered to Cellulose Scaffold.2010

    • Author(s)
      Fukuhara, G.; Nakamura, T.; Yang, C.; Mori, T.; Inoue, Y.
    • Journal Title

      Journal of Organic Chemistry

      Volume: 75 Pages: 4307-4310

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Bio-supramolecular photochirogenesis with molecular chaperone : enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate mediated by prefoldin.2010

    • Author(s)
      Bando, K.; Zako, T.; Sakono, M.; Maeda, M.; Wada, T.; Nishijima, M.; Fukuhara, G.; Yang, C.; Mori, T.; Pace, T.C.S.; Bohne, C.; Inoue, Y
    • Journal Title

      Photochemical & Photobiological Sciences

      Volume: 9 Pages: 655-660

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Combined Experimental and Quantum Chemical Investigation of Chiroptical Properties of Nicotinamide Derivatives with and without Intramolecular Cation-pi Interactions.2009

    • Author(s)
      Shimizu, A., Mori, T., Inoue, Y., Yamada, S.
    • Journal Title

      J.Phys.Chem.A 113(30)

      Pages: 8754-8764

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Supramolecular complexation of N-alkyland N, N'-dialkylpiperazines with cucurbit [6] uril in aqueous solution and in the solid state.2009

    • Author(s)
      Rekharsky, M.V., Yamamura, H., Mori, T., Sato, A., Shiro, M., Lindeman, S.V., Rathore, R., Shiba, K., Ko, Y.H., Selvapalam, N., Kim, K., Inoue, Y.
    • Journal Title

      Chem.Eur.J. 15(8)

      Pages: 1957-1965

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Wavelength Control of Diastereodifferentiating Paterno-Buchi Reaction of Chiral Cyanobenzoates with Diphenylethene through Direct versus Charge-Transfer Excitation.2009

    • Author(s)
      Matsumura, K., Mori, T., Inoue, Y.
    • Journal Title

      J.Am.Chem.Soc. 131(47)

      Pages: 17076-17077

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Enantiodifferentiating Photocyclodimerization of 2-Anthracenecarboxylic Acid Mediated by a Non-Sensitizing Chiral Metallosupramolecular Host.2009

    • Author(s)
      Ke, C., Yang, C., Mori, T., Wada, T., Liu, Y., Inoue, Y.
    • Journal Title

      Angew.Chem., Int.Ed. 48(36)

      Pages: 6675-6677

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Supramolecular complexation and enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid with 4-aminoprolinol derivatives as chiral hydrogen-bonding templates.2009

    • Author(s)
      Kawanami, Y., Pace, T. C. S., Mizoguchi, J.-i., Yanagi, T., Nishijima, M., Mori, T., Wada, T., Bohne, C., Inoue, Y.
    • Journal Title

      J.Org.Chem. 74(20)

      Pages: 7908-7921

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Competitive Enantiodifferentiating Anti-Markovnikov Photoaddition of Water and Methanol to 1, 1-Diphenylpropene Using A Sensitizing Cyclodextrin Host.2009

    • Author(s)
      Fukuhara, G., Mori, T., Inoue, Y.
    • Journal Title

      J.Org.Chem. 74(17)

      Pages: 6714-6727

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Wavelength Control of Diastereodifferentiating Paterno-Buchi Reaction of Chiral Cyanobenzoates with Diphenylethene through Direct vs Charge-Transfer Excitation2009

    • Author(s)
      Matsumura, K.; Mori, T.; Inoue, Y.
    • Journal Title

      Journal of the American Chemical Society 131

      Pages: 17076-17077

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Combined Experimental & Quantum Chemical Investigation of Chiroptical Properties of Nicotinamide Derivatives with and without Intramolecular Cation-pi Interactions2009

    • Author(s)
      Shimizu, A.; Mori, T.; Inoue, Y.; Yamada, S.
    • Journal Title

      Journal of Physical Chemistry A 113

      Pages: 8754-8764

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Enantiodifferentiating Photocyclodimerization of 2-Anthracenecarboxylic Acid Mediated by a Non-Sensitizing Chiral Metallosupramolecular Host2009

    • Author(s)
      Ke, C.; Yang, C.; Mori, T.; Wada, T.; Liu, Y.; Inoue, Y.
    • Journal Title

      Angewandte Chemie, International Edition 48

      Pages: 6675-6677

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Supramolecular complexation of N-alkyl- and N,N'-dialkylpiperazines with cucurbit[6]uril in aqueous solution and in the solid state2009

    • Author(s)
      Rekharsky, M.V.; Yamamura, H.; Mori, T.; Sato, A.; Shiro, M.; Lindeman, S.V.; Rathore, R.; Shiba, K.; Ko, Y.H.; Selvapalam, N.; Kim, K.; Inoue, Y.
    • Journal Title

      Chemistry - A European Journal 15

      Pages: 1957-1965

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Supramolecular complexation/enantiodifferentiating photocyclodimerization of 2-anthra-cenecarboxylicacid with 4-aminoprolinol derivatives as chiral H-bonding templates2009

    • Author(s)
      Kawanami, Y.; Pace, T.C.S.; Mizoguchi, J.-i.; Yanagi, T.; Nishijima, M.; Mori, T.; Wada, T.; Bohne, C.; Inoue, Y.
    • Journal Title

      Journal of Organic Chemistry 74

      Pages: 7908-7921

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Competitive Enantiodifferentiating Anti-Markovnikov Photoaddition of Water and Methanol to 1,1-Diphenylpropene Using A Sensitizing Cyclodextrin Host2009

    • Author(s)
      Fukuhara, G.; Mori, T.; Inoue, Y.
    • Journal Title

      Journal of Organic Chemistry 74

      Pages: 6714-6727

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Presentation] Effects of Irradiation Wave-length on Diastereodifferentiating Paterno-Buchi Reaction of Chiral Cyanobenzoates with Diphenylethene2010

    • Author(s)
      Matsumura, K., Nishiuchi, E., Mori, T., Inoue, Y.
    • Organizer
      5th International Symposium on Macrocyclic and Supramolecular Chemistry
    • Place of Presentation
      Nara, Japan.
    • Related Report
      2010 Final Research Report
  • [Presentation] Experimental and Theoretical Investigations on the Chiroptical Properties of Donor-Acceptor Binaphthyls.2010

    • Author(s)
      Matsumura, K., Nishiuchi, E., Mori, T., Inoue, Y.
    • Organizer
      Dynamic Conformer Population Studied by Circular Dichroism, 22nd International Symposium on Chirality
    • Place of Presentation
      Sapporo, Japan.
    • Related Report
      2010 Final Research Report
  • [Presentation] Solvent and temperature effects on diastereodifferentiating Paterno-Buchi reaction of chiral cyanobenzoates with diphenylethene upon direct and charge-transfer excitations2010

    • Author(s)
      Matsumura, K., Nishiuchi, E., Mori, T., Inoue, Y.
    • Organizer
      Pacifichem 2010
    • Place of Presentation
      Honolulu, Hawaii, USA.
    • Related Report
      2010 Final Research Report
  • [Presentation] 電荷移動錯体の選択的光励起を利用した不斉光反応の制御2010

    • Author(s)
      森直
    • Organizer
      先端有機化学シンポジウム2010
    • Place of Presentation
      立山国際ホテル
    • Related Report
      2010 Final Research Report
  • [Presentation] キラルシクロペンタノン骨格に基づくn-π* 遷移の異方性因子の理論的検討2010

    • Author(s)
      森直・井上佳久
    • Organizer
      第21回基礎有機化学討論会
    • Place of Presentation
      名古屋大学東山キャンパス
    • Related Report
      2010 Final Research Report
  • [Presentation] ドナー・アクセプター型ビナフチル類のキロプティカル特性の実験的・理論的研究2010

    • Author(s)
      西坂政輝・森直・井上佳久
    • Organizer
      円二色性に及ぼす動的コンフォマー分布の影響,2010年光化学討論会
    • Place of Presentation
      千葉大学西千葉キャンパス
    • Related Report
      2010 Final Research Report
  • [Presentation] Effect of Wavelength and Confinement on the Diastereoselective Photoreaction of 1, 1-Dicyano-2-methyl-4-phenyl-1-pentene2010

    • Author(s)
      Mori, T., Nishiuchi, E., Matsumura, K., Saito, H., Inoue, Y.
    • Organizer
      第5回分子情報ダイナミクス研究会
    • Place of Presentation
      大阪大学銀杏会館
    • Related Report
      2010 Final Research Report
  • [Presentation] 絶対不斉合成を志向した理論計算によるシクロペンタノンの異方性因子の予測2010

    • Author(s)
      森直・井上佳久
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学本部キャンパス
    • Related Report
      2010 Final Research Report
  • [Presentation] Effects of Irradiation Wave- length on Diastereodifferenti- ating Paterno-Buchi Reaction of Chiral Cyanobenzoates with Diphenylethene2010

    • Author(s)
      Matsumura, K.; Nishiuchi, E.; Mori, T.; Inoue, Y.
    • Organizer
      5th International Symposium on Macrocyclic and Supramolecular Chemistry
    • Place of Presentation
      Nara, Japan
    • Related Report
      2010 Annual Research Report
  • [Presentation] Experimental and Theoretical Investigations on the Chiroptical Properties of Donor-Acceptor Binaphthyls.Dynamic Conformer Population Studied by Circular Dichroism2010

    • Author(s)
      Nishizaka, M.; Mori, T.; Inoue, Y.
    • Organizer
      22nd International Symposium on Chirality
    • Place of Presentation
      Sapporo, Japan
    • Related Report
      2010 Annual Research Report
  • [Presentation] Solvent and temperature effects on diastereodifferentiating Paterno-Buchi reaction of chiral cyanobenzoates with diphenylethene upon direct and charge-transfer excitations2010

    • Author(s)
      Matsumura, K.; Nishiuchi, E.; Mori, T.; Inoue, Y.
    • Organizer
      Pacifichem 2010
    • Place of Presentation
      Honolulu, Hawaii, USA
    • Related Report
      2010 Annual Research Report
  • [Presentation] Effect of Wavelength and Confinement on the Diastereoselective Photoreaction of Intramolecular Donor-Acceptor Molecules2009

    • Author(s)
      Mori, T.
    • Organizer
      Gordon Research Conference of Photochemistry
    • Place of Presentation
      Bryant University/Smithfield, RI, USA.
    • Related Report
      2010 Final Research Report
  • [Presentation] Effect of Wavelength and Confinement on the Diastereoselective Photoreaction of Intramolecular Donor-Acceptor Molecules2009

    • Author(s)
      Mori, T.
    • Organizer
      Gordon Research Conference of Photochemistry
    • Place of Presentation
      BryantUniv./Smithfield, RI, USA
    • Related Report
      2009 Annual Research Report
  • [Book] Electronic and Magnetic Properties of Chiral Molecules and Supramolecular Architectures : Recent theoretical and experimental advances in the electronic circular dichroisms of planar chiral cyclophanes.2011

    • Author(s)
      Mori, T., Y.Inoue
    • Total Pages
      30
    • Publisher
      Springer
    • Related Report
      2010 Annual Research Report
  • [Remarks] ホームページ

    • URL

      http://www.chem.eng.osaka-u.ac.jp/~inoken/index.php?id=article&lang=ja

    • Related Report
      2010 Final Research Report
  • [Remarks]

    • URL

      http://www.chem.eng.osaka-u.ac.jp/~inoken/index.php?id=article&lang=ja

    • Related Report
      2010 Annual Research Report
  • [Remarks]

    • URL

      http://www.chem.eng.osaka-u.ac.jp/~inoken/index.php?id=article&lang=ja

    • Related Report
      2009 Annual Research Report

URL: 

Published: 2009-04-01   Modified: 2016-04-21  

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