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

• Project/Area Number: 21750044
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Organic chemistry
• Research Institution: Osaka 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: ¥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

Research Products

• [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
  • 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
  • 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
  • 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
  • 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
  • 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)
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • Peer Reviewed
• [Journal Article] Wavelength Control of Diastereodifferentiating Paterno-Buchi Reaction of Chiral Cyanobenzoates with Diphenylethene through Direct vs Charge-Transfer Excitation (2009)
  • Author(s): Matsumura, K.; Mori, T.; Inoue, Y.
  • Journal Title: Journal of the American Chemical Society 131 Pages: 17076-17077
  • Peer Reviewed
• [Journal Article] Combined Experimental & 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: Journal of Physical Chemistry A 113 Pages: 8754-8764
  • 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: Angewandte Chemie, International Edition 48 Pages: 6675-6677
  • Peer Reviewed
• [Journal Article] Supramolecular complexation of N-alkyl- and 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: Chemistry - A European Journal 15 Pages: 1957-1965
  • Peer Reviewed
• [Journal Article] Supramolecular complexation/enantiodifferentiating photocyclodimerization of 2-anthra-cenecarboxylicacid with 4-aminoprolinol derivatives as chiral H-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: Journal of Organic Chemistry 74 Pages: 7908-7921
  • 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: Journal of Organic Chemistry 74 Pages: 6714-6727
  • Peer Reviewed
• [Presentation] Effects of Irradiation Wave-length on Diastereodifferentiating Paterno-Buchi Reaction of Chiral Cyanobenzoates with Diphenylethene (2010)
  • Author(s): Matsumura, K., Nishiuchi, E., Mori, T., Inoue, Y.
  • Organizer: 5th International Symposium on Macrocyclic and Supramolecular Chemistry
  • Place of Presentation: Nara, Japan.
• [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.
• [Presentation] Solvent and temperature effects on diastereodifferentiating Paterno-Buchi reaction of chiral cyanobenzoates with diphenylethene upon direct and charge-transfer excitations (2010)
  • Author(s): Matsumura, K., Nishiuchi, E., Mori, T., Inoue, Y.
  • Organizer: Pacifichem 2010
  • Place of Presentation: Honolulu, Hawaii, USA.
• [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
• [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
• [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
• [Presentation] Effect of Wavelength and Confinement on the Diastereoselective Photoreaction of 1, 1-Dicyano-2-methyl-4-phenyl-1-pentene (2010)
  • 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
• [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
• [Presentation] Effects of Irradiation Wave- length on Diastereodifferenti- ating Paterno-Buchi Reaction of Chiral Cyanobenzoates with Diphenylethene (2010)
  • Author(s): Matsumura, K.; Nishiuchi, E.; Mori, T.; Inoue, Y.
  • Organizer: 5th International Symposium on Macrocyclic and Supramolecular Chemistry
  • Place of Presentation: Nara, Japan
• [Presentation] Experimental and Theoretical Investigations on the Chiroptical Properties of Donor-Acceptor Binaphthyls.Dynamic Conformer Population Studied by Circular Dichroism (2010)
  • Author(s): Nishizaka, M.; Mori, T.; Inoue, Y.
  • Organizer: 22nd International Symposium on Chirality
  • Place of Presentation: Sapporo, Japan
• [Presentation] Solvent and temperature effects on diastereodifferentiating Paterno-Buchi reaction of chiral cyanobenzoates with diphenylethene upon direct and charge-transfer excitations (2010)
  • Author(s): Matsumura, K.; Nishiuchi, E.; Mori, T.; Inoue, Y.
  • Organizer: Pacifichem 2010
  • Place of Presentation: Honolulu, Hawaii, USA
• [Presentation] Effect of Wavelength and Confinement on the Diastereoselective Photoreaction of Intramolecular Donor-Acceptor Molecules (2009)
  • Author(s): Mori, T.
  • Organizer: Gordon Research Conference of Photochemistry
  • Place of Presentation: Bryant University/Smithfield, RI, USA.
• [Presentation] Effect of Wavelength and Confinement on the Diastereoselective Photoreaction of Intramolecular Donor-Acceptor Molecules (2009)
  • Author(s): Mori, T.
  • Organizer: Gordon Research Conference of Photochemistry
  • Place of Presentation: BryantUniv./Smithfield, RI, USA
• [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
• [Remarks] ホームページ
  • URL: http://www.chem.eng.osaka-u.ac.jp/~inoken/index.php?id=article&lang=ja
• [Remarks]
  • URL: http://www.chem.eng.osaka-u.ac.jp/~inoken/index.php?id=article&lang=ja
• [Remarks]
  • URL: http://www.chem.eng.osaka-u.ac.jp/~inoken/index.php?id=article&lang=ja