Studies on Synthesis and Properties of Chlorophyll Oligomers

• Project/Area Number: 18750124
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Functional materials chemistry
• Research Institution: Nagahama Institute of Bio-Science and Technology (2007-2008); Ritsumeikan University (2006)
• Principal Investigator: SASAKI Shin-ichi Nagahama Institute of Bio-Science and Technology, バイオサイエンス学部, 講師 (50317294)
• Research Collaborator: TAMIAKI Hitoshi 立命館大学, 薬学部, 教授 (00192641)
• Project Period (FY): 2006 – 2008
• Project Status: Completed (Fiscal Year 2008)
• Budget Amount: ¥3,840,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥240,000); Fiscal Year 2008: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000); Fiscal Year 2007: ¥1,100,000 (Direct Cost: ¥1,100,000); Fiscal Year 2006: ¥1,700,000 (Direct Cost: ¥1,700,000)
• Keywords: 超分子 / 光合成 / 分子認識 / クロロフィル / クロリン / 光合成色素 / 超分子化学 / 合成化学

Research Abstract

光合成の光収穫系アンテナ部に見出される秩序だった色素配列を模倣して、数と空間配置をコントロールしたクロロフィル集積体を構築し、その構造と機能の解明を行った。クロリン骨格にアセチレン部位を導入する手法を開発し直鎖状2量体を合成したところ、共役系の拡張に伴う吸収スペクトルの変化が観測された。また、エステル鎖で架橋された環状の2,3,4量体クロリンを合成したところ、4量体が特異的にフラーレンを認識して取り込むことを見出した。

Research Products

• [Journal Article] Synthesis, Modification, and Optical Properties of C3-Ethynylated Chlorophyll Derivatives (2008)
  • Author(s): Shin-ichi Sasaki, Keisuke Mizutani, Michio Kunieda, Hitoshi Tamiaki
  • Journal Title: Tetrahedron Lett. 49 Pages: 4113-4115
  • Peer Reviewed
• [Journal Article] Dependence of Photocurrent and Conversion Efficiency of Titania-Based Solar Cell on the Qy Absorption and One Electron-Oxidation Potential of Pheophorbide Sensitizer (2008)
  • Author(s): Xiao-Feng Wang, Yasushi Koyama, Hiroyoshi Nagae, Yuji Wada, Shin-ichi Sasaki, Hitoshi Tamiaki
  • Journal Title: J. Phys. Chem. C 112 Pages: 4418-4426
  • Peer Reviewed
• [Journal Article] 近赤外領域に吸収をもつ蛍光色素の開発 (2008)
  • Author(s): 佐々木真一
  • Journal Title: 光化学 39 Pages: 43-44
  • NAID: 10021068963
• [Journal Article] Synthesis, Modification, and Optical Properties of C3-Ethynylated Chlorophyll Derivatives (2008)
  • Author(s): Shin-ichi Sasaki, Keisuke Mizutani, Michio Kunieda, Hitoshi Tamiaki
  • Journal Title: Tetrahedron Lett 49 Pages: 4113-4115
  • Peer Reviewed
• [Journal Article] Dependence of Photocurrent and Conversion Efficiency of Titania-Based Solar Cell on the Qy Absorption and One Electron-Oxidation Potential of Pheophorbide Sensitizer (2008)
  • Author(s): Xiao-Feng Wang, Yasushi Koyama, Hiroyoshi Nagae, YujiWada, Shin-ichi Sasaki, Hitoshi Tamiaki
  • Journal Title: J. Phys. Chem. C 112 Pages: 4418-4426
  • Peer Reviewed
• [Journal Article] A Facile Synthetic Method for Conversion of Chlorophyll-a to Bacteriochlorophyll-c (2007)
  • Author(s): Shin-ichi Sasaki, Tadashi Mizoguchi, Hitoshi Tamiaki
  • Journal Title: J. Org. Chem. 72 Pages: 4566-4569
  • Peer Reviewed
• [Journal Article] Facile Synthesis of Self-Aggregative Zinc Bacteriochlorins by Modifying Naturally Occurring Chlorophyll-a (2007)
  • Author(s): Michio Kunieda, Kohei Yamamoto, Shin-ichi Sasaki, Hitoshi Tamiaki
  • Journal Title: Chem. Lett. 36 Pages: 936-937
  • NAID: 10019745864
  • Peer Reviewed
• [Journal Article] A Dye-Sensitized Solar Cell Using Pheophytin-Carotenoid Adduct : Enhancement of Photocurrent by Electron and Single-Energy Transfer and by Suppression of Singlet-Triplet Annihilation due to the Presence of the Carotenoid Moiety (2007)
  • Author(s): Xiao-Feng Wang, Yasushi Koyama, Yuji Wada, Shin-ichi Sasaki, Hitoshi Tamiaki
  • Journal Title: Chem. Phys. Lett. 439 Pages: 115-120
  • Peer Reviewed
• [Journal Article] A Dye-Sensitized Solar Cell Using Pheophytin-Carotenoid Adduct: Enhancement of Photocurrent by Electron and Singlet-Energy Transfer and by Suppression of Singlet-Triplet Annibilation due to the Presence of the Carotenoid Moiety (2007)
  • Author(s): Xiao-Feng Wang, Yasushi Koyama, Yuji Wada, Shin-ichi Sasaki, Hitoshi Tamiaki
  • Journal Title: Chem. Phys. Lett. 439 Pages: 115-120
  • Peer Reviewed
• [Journal Article] Facile Synthesis of Self-Aggregative Zinc Bacteriochlorins by Modifying Naturally Occurring Chlorophyll-a (2007)
  • Author(s): Michio Kunieda, Kohei Yamamoto, Shin-ichi Sasaki. Hitoshi Tamiaki
  • Journal Title: Chem. Lett. 36 Pages: 936-937
  • NAID: 10019745864
  • Peer Reviewed
• [Journal Article] Synthesis of Cyclic Chlorophyll Oligomers (2006)
  • Author(s): Shin-ichi Sasaki and Hitoshi Tamiaki
  • Journal Title: Tetrahedron Lett. 47 Pages: 4965-4968
  • Peer Reviewed
• [Journal Article] Effects of Plant Carotenoid Spacers on the Performance of a Dye-Sensitized Solar Cell Using a Chlorophyll Derivative: Enhancement of Photocurrent Determined by One Electron-Oxidation Potential of Each Carotenoid (2006)
  • Author(s): Xiao-Feng Wang, Arihiro Matsuda, Yasushi Koyama, Hiroyoshi Nagae, Shin-ichi Sasaki, Hitoshi Tamiaki, and Yuji Wada
  • Journal Title: Chem. Phys. Lett. 423 Pages: 470-475
  • Peer Reviewed
• [Journal Article] Trifluoroacetyl-Chlorin as a New Chemosensor for Ratiometric Amine Determination (2006)
  • Author(s): Shin-ichi Sasaki, Yuki Kotegawa, and Hitoshi Tamiaki
  • Journal Title: Tetrahedron Lett. 47 Pages: 4849-4852
  • Peer Reviewed
• [Journal Article] Synthesis and Optical Properties of Bacteriochlorophyll-a Derivatives Having Various C3-Substituents on the Bacteriochlorin π-System (2006)
  • Author(s): Shin-ichi Sasaki and Hitoshi Tamiaki
  • Journal Title: J. Org. Chem. 71 Pages: 2648-2654
  • Peer Reviewed
• [Journal Article] Gallium (III) Complexes of Methyl Pyropheophorbide-a as Synthetic Models for Investigation of Diastereomerically Controlled Axial Ligation Towards Chlorophylls (2006)
  • Author(s): Shin-ichi Sasaki, Tadashi Mizoguchi, and Hitoshi Tamiaki
  • Journal Title: Bioorg. Med. Chem. Lett. 16 Pages: 1168-1171
  • Peer Reviewed
• [Journal Article] Gallium (III) Complexes of Methyl Pyropheophorbide-a as Synthetic Models for Investigation of Diastereomerically Controlled Axial Ligation Towards Chlorophylls (2006)
  • Author(s): Shin-ichi Sasaki, Tadashi Mizoguchi, Hitoshi Tamiaki
  • Journal Title: Bioorg.Med.Chem.Lett. 16 Pages: 1168-1171
• [Journal Article] Synthesis and Optical Properties of Bacteriochlorophyll-a Derivatives Having Various C3-Substituents on the Bacteriochlorin π-System (2006)
  • Author(s): Shin-ichi Sasaki, Hitoshi Tamiaki
  • Journal Title: J.Org.Chem. 71 Pages: 2648-2654
• [Journal Article] Trifluoroacetyl-Chlorin as a New Chemosensor for Ratiometric Amine Determination (2006)
  • Author(s): Shin-ichi Sasaki, Yuki Kotegawa, Hitoshi Tamiaki
  • Journal Title: Tetrahedron Lett. 47 Pages: 4849-4852
• [Journal Article] Effects of Plant Carotenoid Spacers on the Performance of a Dye-Sensitized Solar Cell Using a Chlorophyll Derivative : Enhancement of Photocurrent Determined by One Electron-Oxidation Potential of Each Carotenoid (2006)
  • Author(s): Xiao-Feng Wang, Arihiro Matsuda, Yasushi Koyama, Hiroyoshi Nagae, Shin-ichi Sasaki, Hitoshi Tamiaki, Yuji Wada
  • Journal Title: Chem.Phys.Lett. 423 Pages: 470-475
• [Journal Article] Synthesis of Cyclic Chlorophyll Oligomers (2006)
  • Author(s): Shin-ichi Sasaki, Hitosh Tamiaki
  • Journal Title: Tetrahedron Lett. 47 Pages: 4965-4968
• [Presentation] アミン応答性クロロフィル誘導体の合成と色調コントロール (2008)
  • Author(s): 高野宏輔、佐々木真一、Daniel Citterio、小手川雄樹、東希実子、國枝道雄、民秋均、鈴木孝治
  • Organizer: 2008年光化学討論会
  • Place of Presentation: 大阪
• [Presentation] トリフルオロアセチルクロリンを用いたアルコールオプトードの開発 (2008)
  • Author(s): 高野宏輔、佐々木真一、Daniel Citterio、小手川雄樹、東希実子、國枝道雄、民秋均、鈴木孝治
  • Organizer: 日本分析化学会第57年会
  • Place of Presentation: 福岡
• [Presentation] Chlorophyll-Derived Thermochromic Sensor Based on Intramolecular Hemiaminal Formation (2008)
  • Author(s): Shin-ichi Sasaki, Yuki Kotegawa, Kimiko Azuma, Michio Kunieda, Hitoshi Tamiaki
  • Organizer: XXIInd IUPAC symposium on Photochemistry
  • Place of Presentation: Gothenburg, Sweden
• [Presentation] Cooperative C3/C13-Substituent Effects on Optical Properties of Chlorophyll Derivatives (2008)
  • Author(s): Hitoshi Tamiaki, Mari Yoshizato, Michio Kunieda, Shin-ichi Sasaki
  • Organizer: XXIInd IUPAC Symposium on Photochemistry
  • Place of Presentation: Gothenburg, Sweden
• [Presentation] Synthesis and Optical Property of 3-Ethynylated Chlorophyll Derivative (2008)
  • Author(s): Hitoshi Tamiaki, Keisuke Mizutani, Michio Kunieda, Shin-ichi Sasaki
  • Organizer: International Conference on Porphyrins and Phthalocyanines
  • Place of Presentation: Moscow, Russia
• [Presentation] Synthesis of C3-Substituted Chlorophyll Derivatives by Modification of Ethynyl Group at the 3-Position (2008)
  • Author(s): Hitoshi Tamiaki, Keisuke Mizutani, Michio Kunieda, Shin-ichi Sasaki
  • Organizer: International Conference on Porphyrins and Phthalocyanines
  • Place of Presentation: Moscow, Russia
• [Presentation] Optical Properties of Synthetic Chlorophyll Derivatives Possessing Various Substituents at the C3 and C13 Positions (2008)
  • Author(s): Hitoshi Tamiaki, Mari Yoshizato, Michio Kunieda, Shin-ichi Sasaki
  • Organizer: Fifth International Workshop on Supramolecular Nanoscience of Chemically Programmed Pigments
  • Place of Presentation: Kusatsu, Shiga, Japan
• [Presentation] Synthesis and Optical Property of Ethynylated Chlorophyll Derivatives at the C3 Position (2008)
  • Author(s): Hitoshi Tamiaki, Keisuke Mizutani, Michio Kunieda, Shin-ichi Sasaki
  • Organizer: Fifth International Workshop on Supramolecular Nanoscience of Chemically Programmed Pigments
  • Place of Presentation: Kusatsu, Shiga, Japan
• [Presentation] 硫黄含有クロロフィル類の合成と物性 (2008)
  • Author(s): 民秋均、吉里麻里、國枝道雄、佐々木真一
  • Organizer: 日本化学会第88春季年会
  • Place of Presentation: 東京
• [Presentation] 3位にエチニル基を有するクロロフィル類の合成と物性 (2008)
  • Author(s): 民秋均、水谷佳祐、國枝道雄、佐々木真一
  • Organizer: 日本化学会第88春季年会
  • Place of Presentation: 東京
• [Presentation] 分子内にスイッチ機能を有するクロロフィル温度センサーの合成と物性 (2008)
  • Author(s): 小手川雄樹、佐々木真一、民秋均
  • Organizer: 日本化学会第88春季年会
  • Place of Presentation: 東京
• [Presentation] Synthesis and Optical Property of Ethynylated Chlorophyll Derivatives at the C3 Position (2008)
  • Author(s): Hitoshi Tamiaki, Keisuke Mizutani, Michio Kunieda, Shin-ichi Sasaki
  • Organizer: Fifth International Workshop on Supramolecular Nanoscience of Chemically Programmed Pigments
  • Place of Presentation: Ritsumeikan University, Kusatsu, Shiga, Japan
• [Presentation] Optical Properties of Synthetic Chlorophyll Derivatives Possessing Various Substituents at the C3 and C13 Positions (2008)
  • Author(s): Hitoshi Tamiaki, Mari Yoshizato, Michio Kunieda, Shin-ichi Sasaki
  • Organizer: Fifth International Workshop on Supramolecular Nanoscience of Chemically Programmed Pigments
  • Place of Presentation: Ritsumeikan University, Kusatsu, Shiga, Japan
• [Presentation] Synthesis of C3-Substituted Chlorophyll Derivatives by Modification of Ethynyl Group at the 3-Position (2008)
  • Author(s): Hitoshi Tamiaki, Keisuke Mizutani, Michio Kunieda, Shin-ichi Sasaki
  • Organizer: International Conference on Porphyrins am Phthalocvanines
  • Place of Presentation: Moscow, Russia
• [Presentation] Chlorophyll-Derived Thermochromic Sensor Based on Intramolecular Hemiaminal Formation (2008)
  • Author(s): Shin-ichi Sasaki, Yuki Kotegawa, Kimiko Azuma, Michio Kunieda, Hitoshi Tamiaki
  • Organizer: XXII^<nd> IUPAC Symposium on Photochemistry
  • Place of Presentation: Gothenburg, Sweden
• [Presentation] トリフルオロアセチルクロリンを用いたアルコールオプトードの開発 (2008)
  • Author(s): 高野宏輔、佐々木真一、DanielCitterio、小手川雄樹、東希実子、國枝道雄、民秋均、鈴木孝治
  • Organizer: 日本分析化学会第57年会
  • Place of Presentation: 福岡大学(福岡県)
• [Presentation] アミン応答性クロロフィル誘導体の合成と色調コントロール (2008)
  • Author(s): 高野宏輔、佐々木真一、Danielcitterio、小手川雄樹、東希実子、國枝道雄、民秋均、鈴木孝治
  • Organizer: 2008年光化学討論会
  • Place of Presentation: 大阪府立大学(大阪府)
• [Presentation] Chlorophyll-Derived Chemosensor for Visual Amine Detection (2007)
  • Author(s): Shin-ichi Sasaki, Yuki Kotegawa, Hitoshi Tamiaki
  • Organizer: ISNA-12, The 12th International Symposium on Novel Aromatic Compounds
  • Place of Presentation: Awajishima-Hyougo, Japan
• [Presentation] 3位にカルボニル基を有するクロロフィル誘導体の合成と物性 (2007)
  • Author(s): 民秋均、小手川雄樹、佐々木真一
  • Organizer: 光化学討論会
  • Place of Presentation: 長野
• [Presentation] Chlorophyll-Derived Chemosensor for Visual Amine Detection (2007)
  • Author(s): Shin-ichi Sasaki, Yuki Kotegawa, Hitoshi Tamiaki
  • Organizer: ISNA-12, The 12th International Symposium on Novel Aromatic Compounds
  • Place of Presentation: Awaijshima-Hyougo, Japan
• [Presentation] Synthesis of Bacteriochlorophyll-c Derivatives by Palladium-Catalyzed Cross-Coupling Methylation of the Corresponding 20-Bromo-Chlorin (2006)
  • Author(s): Shin-ichi Sasaki, Hitoshi Tamiaki
  • Organizer: IKCOC-10, The Tenth International Kyoto Conference on New Aspects of Organic Chemistry
  • Place of Presentation: Kyoto, Japan
• [Presentation] Chlorophyll-Derived Chemosensor for Ratiometric Amine Determination (2006)
  • Author(s): Shin-ichi Sasaki, Yuki Kotegawa, Hitoshi Tamiaki
  • Organizer: Third International Workshop on Supramolecular Nanoscience of Chemically Programmed Pigments
  • Place of Presentation: Shiga, Japan
• [Presentation] Guest-Induced Conformational Control of Cyclic Chlorophyll Oligomers (2006)
  • Author(s): Shin-ichi Sasaki, Hitoshi Tamiaki
  • Organizer: Third International Workshop on Supramolecular Nanoscience of Chemically Programmed Pigments
  • Place of Presentation: Shiga, Japan
• [Presentation] Immobilization of Chlorophyll Derivatives Possessing a Disulfide Moiety on a Gold Nanoparticle (2006)
  • Author(s): Hitoshi Tamiaki, Hiromaru Yamamoto, Yoshitaka Saga, Shin-ichi Sasaki
  • Organizer: XXIst IUPAC Symposium on Photochemistry
  • Place of Presentation: Kyoto, Japan
• [Presentation] Synthesis of Trifluoromethylated Chlorophyll Derivatives and Their Optical Properties (2006)
  • Author(s): Hitoshi Tamiaki, Yuki Kotegawa, Shin-ichi Sasaki
  • Organizer: XXIst IUPAC Symposium on Photochemistry
  • Place of Presentation: Kyoto, Japan
• [Presentation] Synthesis and Optical Properties of Covalently Linked Chlorophyll Dimers (2006)
  • Author(s): Hitoshi Tamiaki, Sai Fujii, Shin-ichi Sasaki
  • Organizer: XXIst IUPAC Symposium on Photochemistry
  • Place of Presentation: Kyoto, Japan
• [Presentation] Asymmetric Fifth Axial Ligation for Ga(III) Chlorophylls (2006)
  • Author(s): Hitoshi Tamiaki, Tadashi Mizoguchi, Shin-ichi Sasaki
  • Organizer: XXIst IUPAC Symposium on Photochemistry
  • Place of Presentation: Kyoto, Japan
• [Presentation] トリフルオロメチル基を有するクロロフィル誘導体の合成と会合挙動 (2006)
  • Author(s): 小手川雄樹、佐々木真一、民秋均
  • Organizer: 第19回配位化合物の光化学討論会
  • Place of Presentation: 茨城
• [Presentation] オリゴメチレン架橋鎖を有するクロロフィル誘導体の合成 (2006)
  • Author(s): 民秋均、武部洋、佐々木真一
  • Organizer: 日本化学会第86春季年会
  • Place of Presentation: 東京