Development and exploration of expanded porphyrins bearing intramolecular conjugation bridges

• Project/Area Number: 22750031
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Organic chemistry
• Research Institution: Chiba University
• Principal Investigator: SUZUKI Masaaki 千葉大学, 大学院・薬学研究院, 助教 (90506891)
• Project Period (FY): 2010 – 2011
• Project Status: Completed (Fiscal Year 2011)
• Budget Amount: ¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000); Fiscal Year 2011: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000); Fiscal Year 2010: ¥2,860,000 (Direct Cost: ¥2,200,000、Indirect Cost: ¥660,000)
• Keywords: ポルフィリノイド / 環拡張ポルフィリン / ヘキサフィリン / ペンタフィリン / 金属錯体 / 芳香族性 / アヌレノアヌレン

Research Abstract

Introduction of intramolecular bridging structures to expanded porphyrins was investigated for accomplishment of [4n]annuleno[4n']annulene frameworks and study on their aromaticity. A brominated product of N-fused pentaphyrin provided a newly formed π-plane consisting of a conjugated bridging skeleton after complicated ring-opening, -closing reactions and its proton NMR spectrum exhibited a ring current effect indicating an aromatic natur of the entire molecules.

Research Products

• [Journal Article] 「Synthesis, Structure, and Aromaticity of the Nickel(II) Complex of Pyricorrole, a Molecular Hybrid of Porphyrin and Corrole (2012)
  • Author(s): Saburo Neya, Masaaki Suzuki, Takashi Matsugae, Tyuji Hoshino
  • Journal Title: 『Inorganic Chemistry 』American Chemical Society Volume: 51巻 Pages: 3891-3895
  • Peer Reviewed
• [Journal Article] Synthesis, Structure, and Aromaticity of the Nickel (II) Complex of Pyricorrole, a Molecular Hybrid of Porphyrin and Corrole (2012)
  • Author(s): Saburo Neya, Masaaki Suzuki, Takashi Matsugae, Tyuji Hoshino
  • Journal Title: Inorganic Chemistry Volume: 51 Issue: 6 Pages: 3891-3895
  • DOI: 10.1021/ic3001043
  • Peer Reviewed
• [Journal Article] Fabrications of potentialimaging probes based on a β -alkylsubstituted porphyrin with aterpyridine external coordinationsite (2011)
  • Author(s): Masaaki Suzuki, Tomoya Uehara, Yasushi Arano, Tyuji Hoshino, Saburo Neya
  • Journal Title: 『Tetrahedron Letters』, Elsevier Volume: 52巻 Pages: 7164-7167
  • Peer Reviewed
• [Journal Article] Conformation dynamics of non-,singly- and doubly-N-fused[28]hexaphyrins revealed byphotophysical studies (2011)
  • Author(s): Jong Min Lim, Mitsunori Inoue, Young Mo Sung, Masaaki Suzuki, Tomohiro Higashino, Atsuhiro Osuka, Dongho Kim
  • Journal Title: 『Chemical Communications 』, Royal Society of Chemistry Volume: 47巻 Pages: 3960-3962
  • Peer Reviewed
• [Journal Article] Fabrications of Potential Imaging Probes Based on a β-Alkyl Substituted Porphyrin With a Terpyridine External Coordination Site (2011)
  • Author(s): Masaaki Suzuki, Tomoya Uehara, Yasushi Arano, Tyuji Hoshino, Saburo Neya
  • Journal Title: Tetrahedron Letters Volume: 52 Issue: 52 Pages: 7164-7167
  • DOI: 10.1016/j.tetlet.2011.10.132
  • Peer Reviewed
• [Journal Article] Conformation dynamics of non-, singly- and doubly-N-fused[28]hexaphyrins revealed by photophysical studies (2011)
  • Author(s): J.M.Lim, M.Inoue, Y.M.Sung, M.Suzuki, T.Higashino, A.Osuka, D.Kim
  • Journal Title: Chemical Communications Volume: 47 Pages: 3960-3962
  • Peer Reviewed
• [Journal Article] Molecular Insight of Intrinsic Heme Distortion to the Ligand Binding in Hemoprotein (2010)
  • Author(s): Saburo Neya, Masaaki Suzuki, Teruaki Komatsu, Mikio Nakamura, Hideki Kandori
  • Journal Title: 『Biochemistry』, American Chemical Society Volume: 49巻 Pages: 5642-5650
  • Peer Reviewed
• [Journal Article] Water-soluble doubly N-confused hexaphyr in : A near-IR fluorescent Zn(II) ion sensor in water (2010)
  • Author(s): Yoshiya Ikawa, Mari Takeda, Masaaki Suzuki, Atsuhiro Osuka, Hiroyuki Furuta
  • Journal Title: 『Chemical Communications 』,Royal Society of Chemistry Volume: 46巻 Pages: 5689-5691
  • Peer Reviewed
• [Journal Article] Water-soluble doubly N-confused hexaphyrin : A near-IR fluore scent Zn(II) ion sensor in water (2010)
  • Author(s): Y.Ikawa, M.Takeda, M.Suzuki, A.Osuka
  • Journal Title: Chemical Communications Volume: 46 Pages: 5689-5691
  • Peer Reviewed
• [Journal Article] Molecular Insight of Intrinsic Heme Distortion to the Ligand Binding in Hemoprotein (2010)
  • Author(s): Neya, S., Suzuki, M., Hoshino, T., Ode, H., Imai, K., Komatsu, T., Ikezaki, A., Nakamura, M., Furutani, Y., Kandori, H.
  • Journal Title: Biochemistry Volume: 49 Pages: 5642-5650
  • Peer Reviewed
• [Presentation] インフルエンザエンドヌレアーゼ活性部位の計算機解析と阻害化合物の探索 (2012)
  • Author(s): 不動聡志, 石井和彦, 小川博史, 松浦崇晃, 柳田浩, 額賀路嘉, 山本典生, 鈴木優章, 根矢三郎, 星野忠次
  • Organizer: 日本薬学会第132年会
  • Place of Presentation: 北海道大学(北海道)
  • Year and Date: 2012-03-30
• [Presentation] ポルフィリンをベースにした腫瘍選択的SPECTプローブの開発 (2012)
  • Author(s): 鈴木優章, 根矢三郎, 星野忠次, 上原知也, 荒野泰
  • Organizer: 日本薬学会第132年会
  • Place of Presentation: 北海道大学(北海道)
  • Year and Date: 2012-03-30
• [Presentation] 人工酸素運搬体のための非平面ヘムの開発と応用 (2012)
  • Author(s): 根矢三郎, 鈴木優章, 星野忠次
  • Organizer: 日本薬学会第132年会
  • Place of Presentation: 北海道大学(北海道)
  • Year and Date: 2012-03-30
• [Presentation] ポルフィリンをベースにした腫瘍選択的SPECTプローブの開発 (2012)
  • Author(s): 鈴木優章, 根矢三郎, 星野忠次, 上原知也, 荒野泰
  • Organizer: 日本化学会第92春季年会
  • Place of Presentation: 慶応大学(神奈川県)
  • Year and Date: 2012-03-26
• [Presentation] 新規ポルフィリン異性体ピリコロールの合成 (2012)
  • Author(s): 鈴木優章, 松ヶ枝隆, 星野忠次, 根矢三郎
  • Organizer: 第59回応用物理学関係連合講演会
  • Place of Presentation: 早稲田大学(東京都)
  • Year and Date: 2012-03-17
• [Presentation] 新規ポルフィリン異性体"ピリコロール"の合成 (2012)
  • Author(s): 鈴木優章, 松ヶ枝隆, 星野忠次, 根矢三郎
  • Organizer: 第59回応用物理学関係連合講演会
  • Place of Presentation: 早稲田大学(東京都)
  • Year and Date: 2012-03-17
• [Presentation] ポルフィリンをベースにした腫瘍選択的SPECTプローブの開発 (2011)
  • Author(s): 鈴木優章, 根矢三郎, 星野忠次, 上原知也, 荒野泰
  • Organizer: 第21回基礎有機化学討論会
  • Place of Presentation: つくば国際会議場(茨城県)
  • Year and Date: 2011-09-21
• [Presentation] ポルフィリンとコロールの分子ハイブリッドをつくる (2011)
  • Author(s): 根矢三郎, 鈴木優章, 星野忠次
  • Organizer: 第61回錯体化学討論会
  • Place of Presentation: 岡山理科大学(岡山県)
  • Year and Date: 2011-09-18
• [Presentation] 人工酸素運搬物質開発のための非平面性ポルフィリンの合成と性質 (2011)
  • Author(s): 根矢三郎, 鈴木優章, 星野忠次
  • Organizer: 日本薬学会第131年会
  • Place of Presentation: ツインメッセ静岡(静岡県)
  • Year and Date: 2011-03-29
• [Presentation] βアルキル置換ヘキサフィリンの合成 (2011)
  • Author(s): 鈴木優章, 星野忠次, 根矢三郎
  • Organizer: 日本薬学会第131年会
  • Place of Presentation: ツインメッセ静岡(静岡県)
  • Year and Date: 2011-03-29
• [Presentation] βアルキル置換ヘキサフィリン(1.1.1.1.1.1)の合成 (2011)
  • Author(s): 鈴木優章
  • Organizer: 日本薬学会第131年会
  • Place of Presentation: ツインメッセ静岡(静岡県)
  • Year and Date: 2011-03-29
• [Presentation] βアルキル置換ヘキサフィリンの合成 (2011)
  • Author(s): 鈴木優章, 星野忠次, 根矢三郎
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 神奈川大学(神奈川県)
  • Year and Date: 2011-03-26
• [Presentation] βアルキル置換ヘキサフィリン(1.1.1.1.1.1)の合成 (2011)
  • Author(s): 鈴木優章
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 神奈川大学(神奈川県)
  • Year and Date: 2011-03-26
• [Presentation] 新規ポルフィリン異性体"ピリコロール"の合成 (2011)
  • Author(s): 鈴木優章, 松ヶ枝隆, 星野忠次, 根矢三郎
  • Organizer: 第58回応用物理学関係連合講演会
  • Place of Presentation: 神奈川工科大学(神奈川県)
  • Year and Date: 2011-03-25
• [Presentation] 新規ポルフィリン異性体"ピリコロール"の合成 (2011)
  • Author(s): 鈴木優章
  • Organizer: 第58回 応用物理学関係連合講演会
  • Place of Presentation: 神奈川工科大学(神奈川県)
  • Year and Date: 2011-03-25
• [Presentation] Synthesis and Characterization of β .Alkyl Substituted Hexaphyrin (2010)
  • Author(s): Masaaki Suzuki, Tyuji Hoshino, Saburo Neya
  • Organizer: The International Chemical Congress of Pacific Basin Societies 2010
  • Place of Presentation: Hawaii Convention Center (USA)
  • Year and Date: 2010-12-17
• [Presentation] Synthesis and Characterization of β-Alkyl Substituted Hexaphyrin(1.1.1.1.1.1) (2010)
  • Author(s): Masaaki Suzuki
  • Organizer: The International Chemical Congress of Pacific Basin Societies 2010
  • Place of Presentation: Hawaii Convention Center
  • Year and Date: 2010-12-17
• [Presentation] Functional Anomaly of Hemoprote in Induced by Nonplanar Deformation of Heme (2010)
  • Author(s): Saburo Neya, Masaaki Suzuki, Tyuji Hoshino
  • Organizer: 第60回錯体化学討論会
  • Place of Presentation: 大阪大学(大阪府)
  • Year and Date: 2010-09-28
• [Presentation] Functional Anomaly of Hemoprotein Induced by Nonplanar Deformation of Heme (2010)
  • Author(s): Saburo Neya
  • Organizer: 第60回錯体化学討論会
  • Place of Presentation: 大阪大学(大阪府)
  • Year and Date: 2010-09-28
• [Presentation] 新規ポルフィリン異性体ピリコロールの合成 (2010)
  • Author(s): 根矢三郎, 松ヶ枝隆, 鈴木優章, 星野忠次
  • Organizer: 第21回基礎有機化学討論会
  • Place of Presentation: 名古屋大学(愛知県)
  • Year and Date: 2010-09-09
• [Presentation] 新規ポルフィリン異性体"ピリコロール"の合成 (2010)
  • Author(s): 鈴木優章
  • Organizer: 第21回基礎有機化学討論会
  • Place of Presentation: 名古屋大学(愛知県)
  • Year and Date: 2010-09-09
• [Presentation] Fusion reactions in[26]Hexaphyrins to exhibit distinct Mobius aromaticity (2010)
  • Author(s): Mitsunori Inoue, Kil Suk Kim, Dongho Kim, Jong Min Lim, Atsuhiro Osuka, Jae-Yoon Shin, Masaaki Suzuki, Sumito Tokuji
  • Organizer: 6th International Conference on Porphyrins and Phthalocyanines
  • Place of Presentation: Hyatt Regency Tamaya Resort & Spa Slideshow(USA)
  • Year and Date: 2010-07-08
• [Presentation] Fusion reactions in [26]Hexaphyrins to exhibit distinct Mobius aromaticity (2010)
  • Author(s): Mitsunori Inoue
  • Organizer: 6th International Conference on Porphyrins and Phthalocyanines
  • Place of Presentation: Hyatt Regency Tamaya Resort & Spa Slideshow (USA)
  • Year and Date: 2010-07-08
• [Presentation] Molecular Insight of Heme Deformation to the Ligand Binding to Hemoprotein (2010)
  • Author(s): Saburo Neya, Tyuji Hoshino, Masaaki Suzuki
  • Organizer: 6th International Conference on Porphyrins and Phthalocyanines
  • Place of Presentation: Hyatt Regency Tamaya Resort & Spa Slideshow (USA)
  • Year and Date: 2010-07-07
• [Presentation] Novel structural factor that regulates theoxygen binding properties of myoglobin (2010)
  • Author(s): 鈴木優章, 星野忠次, 根矢三郎
  • Organizer: 第20回金属の関与する生体関連反応シンポジウム
  • Place of Presentation: 徳島文理大学(徳島県)
  • Year and Date: 2010-06-26
• [Presentation] Novel structural factor that regulates the oxygen binding properties of myoglobin (2010)
  • Author(s): Saburo Neya
  • Organizer: 第20回金属の関与する生体関連反応シンポジウム
  • Place of Presentation: 徳島文理大学(徳島県)
  • Year and Date: 2010-06-26
• [Presentation] Synthesis and Characterization ofβ Alkyl Substituted Hexaphyrin (2010)
  • Author(s): 鈴木優章, 星野忠次, 根矢三郎
  • Organizer: 第20回金属の関与する生体関連反応シンポジウム
  • Place of Presentation: 徳島文理大学(徳島県)
  • Year and Date: 2010-06-25
• [Presentation] Synthesis and Characterization of β-Alkyl Substituted Hexaphyrin(1.1.1.1.1.1) (2010)
  • Author(s): Masaaki Suzuki
  • Organizer: 第20回金属の関与する生体関連反応シンポジウム
  • Place of Presentation: 徳島文理大学(徳島県)
  • Year and Date: 2010-06-25
• [Presentation] Synthesis and Characterization of β-Alkyl Substituted Hexaphyrin (2010)
  • Author(s): Masaaki Suzuki, Tyuji Hoshino, Saburo Neya
  • Organizer: 5th International Symposium on Macrocyclic and Supramolecular Chemistry
  • Place of Presentation: 奈良県新公会堂(奈良県)
  • Year and Date: 2010-06-07
• [Presentation] Synthesis and Characterization of β-Alkyl Substituted Hexaphyrin(1.1.1.1.1.1) (2010)
  • Author(s): Masaaki Suzuki
  • Organizer: 5th International Symposium on Macrocyclic and Supramolecular Chemistry
  • Place of Presentation: 奈良県新公会堂(奈良県)
  • Year and Date: 2010-06-07