Structural Control and Functionalization of Giant Porphyrin Arrays

• Project/Area Number: 20750031
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Organic chemistry
• Research Institution: Kyoto University
• Principal Investigator: ARATANI Naoki Kyoto University, 大学院・理学研究科, 助教 (60372562)
• Project Period (FY): 2008 – 2009
• Project Status: Completed (Fiscal Year 2009)
• Budget Amount: ¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000); Fiscal Year 2009: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000); Fiscal Year 2008: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
• Keywords: 構造有機化学 / 物理有機化学 / ポルフィリン / 励起エネルギー移動 / 機能性有機分子 / 有機合成 / 超分子化学 / 構造・機能 / ナノ材料

Research Abstract

As an effective synthetic protocol, Pd-catalyzed Suzuki-Miyaura reaction between arylbromide and boryl-porphyrin was explored, which has been used for the construction of various functional oligomeric porphyrinoids. The application of such methodologies has proven to be very powerful to create new types of porphyrin arrays, which have their own intriguing structures and properties. On the basis of this strategy, we have prepared bithiophene-porphyrin hybrid nanorings, 2,6-pyridylene-bridged β-to-β porphyrin nanorings, and a series of directly meso-β doubly linked porphyrin rings.

Research Products

• [Journal Article] Porphyrin " LEGO Block" Strategy To Construct Directly meso-βDoubly Linked Porphyrin Rings (2010)
  • Author(s): Jianxin Song, Naoki Aratani, Pyosang Kim, Dongho Kim, Hiroshi Shinokubo, Atsuhiro Osuka
  • Journal Title: Angew. Chem. Int. Ed. 49(印刷中)
  • Peer Reviewed
• [Journal Article] Bithiophene - Porphyrin Hybrid Nanorings (2010)
  • Author(s): Kenta Osawa, Jianxin Song, Ko Furukawa, Hiroshi Shinokubo, Naoki Aratani, Atsuhiro Osuka
  • Journal Title: Chem. Asian J. 5 Pages: 764-767
  • Peer Reviewed
• [Journal Article] Strategic Synthesis of 2, 6-Pyridylene-Bridged β-to-βPorphyrin Nanorings through Cross-Coupling (2010)
  • Author(s): Jianxin Song, Pyosang Kim, Naoki Aratani, Dongho Kim, Hiroshi Shinokubo, Atsuhiro Osuka
  • Journal Title: Chem. Eur. J. 16 Pages: 3009-3012
  • Peer Reviewed
• [Journal Article] (2010)
  • Author(s): Harapriya Rath, Sumito Tokuji, Naoki Aratani, Ko Furukawa, Jong Min Lim, Dongho Kim, Hiroshi Shinokubo, Atsuhiro Osuka
  • Journal Title: Angew. Chem. Int. Ed. 49 Pages: 1489-1491
  • Peer Reviewed
• [Journal Article] Wasielewski (2010)
  • Author(s): Thea M. Wilson, Takaaki Hori, Min-Chul Yoon, Naoki Aratani, Atsuhiro Osuka, Dongho Kim, Michael R.
  • Journal Title: J. Am. Chem. Soc. 132 Pages: 1383-1388
  • Peer Reviewed
• [Journal Article] Bithiophene-Porphyrin Hybrid Nanorings (2010)
  • Author(s): K.Osawa, J.Song, K.Furukawa, H.Shinokubo, N.Aratani, A.Osuka
  • Journal Title: Chem.Asian J. 5 Pages: 764-767
  • Peer Reviewed
• [Journal Article] Porphyrin LEGO Block Strategy to Construct Directly meso-β Doubly Linked Porphyrin Rings (2010)
  • Author(s): J.Song, N.Aratani, P.Kim, D.Kim, H.Shinokubo, A.Osuka
  • Journal Title: Angew.Chem.Int.Ed. 49(掲載決定)
  • Peer Reviewed
• [Journal Article] Palladium-Catalyzed Dimerization of meso- Bromoporphyrins: Highly Regioselective meso -βCoupling through Unprecedented Remote C-H Bond Cleavage (2009)
  • Author(s): Sumito Tokuji, Taiga Yurino, Naoki Aratani, Hiroshi Shinokubo, Atsuhiro Osuka
  • Journal Title: Chem. Eur. J. 15 Pages: 12208-12211
  • Peer Reviewed
• [Journal Article] Structural Dependence on Excitation Energy Migration Processes in Artificial Light Harvesting Cyclic Zinc(II) Porphyrin Arrays (2009)
  • Author(s): Min-Chul Yoon, Sung Cho, Pyosang Kim, Takaaki Hori, Naoki Aratani, Atsuhiro Osuka, Dongho Kim
  • Journal Title: J. Phys. Chem. B 113 Pages: 15074-15082
  • Peer Reviewed
• [Journal Article] Selective Formation of a Single Atropisomer of meso - meso-Linked ZnII Diporphyrin through Supramolecular Self-Assembly (2009)
  • Author(s): Chihiro Maeda, Taisuke Kamada, Naoki Aratani, Takahiro Sasamori, Norihiro Tokitoh, Atsuhiro Osuka
  • Journal Title: Chem. Eur. J. 15 Pages: 9681-9684
  • Peer Reviewed
• [Journal Article] Synthesis of Extremelyπ-Extended Porphyrin Tapes from Hybrid meso-meso Linked Porphyrin Arrays: An Approach Towards the Conjugation Length (2009)
  • Author(s): Toshiaki Ikeda, Naoki Aratani, Atsuhiro Osuka
  • Journal Title: Chem. Asian J. 4 Pages: 1248-1256
  • Peer Reviewed
• [Journal Article] Structural Factors Determining Photophysical Properties of Directly Linked Zinc(II) Porphyrin Dimers: Linking Position, Dihedral Angle, and Linkage Length (2009)
  • Author(s): Sung Cho, Min-Chul Yoon, Jong Min Lim, Pyosang Kim, Naoki Aratani, Yasuyuki Nakamura, Toshiaki Ikeda, Atsuhiro Osuka, Dongho Kim
  • Journal Title: J. Phys. Chem. B 113 Pages: 10619-10627
  • Peer Reviewed
• [Journal Article] Meso-βDoubly Linked Zn(II) Porphyrin Trimers: Distinct anti-versus-syn Effects on Their Photophysical Properties (2009)
  • Author(s): Toshiaki Ikeda, Naoki Aratani, Shanmugam Easwaramoorthi, Dongho Kim, Atsuhiro Osuka
  • Journal Title: Org. Lett. 11 Pages: 3080-3083
  • Peer Reviewed
• [Journal Article] Post- Modification of meso - meso-Linked Porphyrin Arrays by Iridium and Rhodium Catalyses for Tuning of Energy Gap (2009)
  • Author(s): Jinping Chen, Naoki Aratani, Hiroshi Shinokubo, Atsuhiro Osuka
  • Journal Title: Chem. Asian J. 4 Pages: 1126-1133
  • Peer Reviewed
• [Journal Article] Bis-rhodium hexaphyrins: metalation of [28]hexaphyrin and a smooth Huckel aromatic - antiaromatic interconversion (2009)
  • Author(s): Harapriya Rath, Naoki Aratani, Jong Min Lim, Jae Seok Lee, Dongho Kim, Hiroshi Shinokubo, Atsuhiro Osuka
  • Journal Title: Chem. Commun. Pages: 3762-3764
  • Peer Reviewed
• [Journal Article] Determination of the Superradiance Coherence Length of Directly Linked Linear Porphyrin Arrays at the Single-Molecule Level (2009)
  • Author(s): Jaesung Yang, Hyejin Yoo, Naoki Aratani, Atsuhiro Osuka, Dongho Kim
  • Journal Title: Angew. Chem. Int. Ed. 48 Pages: 4323-4327
  • Peer Reviewed
• [Journal Article] Facile synthesis and photophysical properties of 1, 2- phenylene-bridged porphyrin dimers (2009)
  • Author(s): Kenta Osawa, Naoki Aratani, Atsuhiro Osuka
  • Journal Title: Tetrahedron Lett. 50 Pages: 3333-3337
  • Peer Reviewed
• [Journal Article] Zwitterionic Corroles: Regioselective Nucleophilic Pyridination of a Doubly Linked Biscorrole (2009)
  • Author(s): Satoru Hiroto, Naoki Aratani, Naoki Shibata, Yoshiki Higuchi, Takahiro Sasamori, Norihiro Tokitoh, Hiroshi Shinokubo, Atsuhiro Osuka
  • Journal Title: Angew. Chem. Int. Ed. 48 Pages: 2388-2390
  • Peer Reviewed
• [Journal Article] Fluorescence Dynamics of Directly Meso-Meso Linked Porphyrin Rings Probed by Single Molecule Spectroscopy (2009)
  • Author(s): Hyejin Yoo, Jaesung Yang, Yasuyuki Nakamura, Naoki Aratani, Atsuhiro Osuka, Dongho Kim
  • Journal Title: J. Am. Chem. Soc. 131 Pages: 1488-1494
  • Peer Reviewed
• [Journal Article] Meso-beta Doubly Linked Zn(II) Porphyrin Trimers : Distinct anti-versus-syn Effects on Their Photophysical Properties (2009)
  • Author(s): T.Ikeda, N.Aratani, S.Easwaramoorthi, D.Kim, A.Osuka
  • Journal Title: Org.Lett. 11 Pages: 3080-3083
  • Peer Reviewed
• [Journal Article] Synthesis of Extremely p-Extended Porphyrin Tapes from Hybrid meso-meso Linked Porphyrin Arrays : An Approach Towards the Conjugation Length (2009)
  • Author(s): T.Ikeda, N.Aratani, A.Osuka
  • Journal Title: Chem.Asian J. 4 Pages: 1248-1256
  • Peer Reviewed
• [Journal Article] π-Conjugation Enlargement Toward the Creation of Multi-porphyrinic Systems with Large Two-photon Absorption Properties (2009)
  • Author(s): N. Aratani, D. Kim, A. Osuka
  • Journal Title: Chem. Asian J. 4
  • Peer Reviewed
• [Journal Article] Bis-rhodium hexaphyrins : metalation of [28]hexaphyrin and a smooth Huckel aromatic-antiaromatic interconversion (2009)
  • Author(s): H. Rath, N. Aratani, J. M. Lim, J. S. Lee, D. Kim, H. Shinokubo, A. Osuka
  • Journal Title: Chem. Commun
  • Peer Reviewed
• [Journal Article] Synthesis and characterizations of free base and Cu(II) complex of a porphyrin sheet (2008)
  • Author(s): Yasuyuki Nakamura, Naoki Aratani, Ko Furukawa, Atsuhiro Osuka
  • Journal Title: Tetrahedron 64 Pages: 11433-11439
  • Peer Reviewed
• [Journal Article] Regioselective [3+4] Cycloaddition of an Azomethine Ylide to Meso-meSo, β-β, β'-β'Triply Linked Diporphyrins (2008)
  • Author(s): T. Tanaka, Y. Nakamura, N.Aratani, and A. Osuka
  • Journal Title: Tetrahedron Letters 49 Pages: 3308-3311
  • Peer Reviewed
• [Journal Article] 2, 5-Thionylene-Bridged Triangular and Linear Porphytin Trimers (2008)
  • Author(s): J. Song, S. Y. Jang, S. Yamaguchi J. Sankar, S.. Hiroto, N. Aratani, J.-Y. Shin, S. Easwaramoorthi, K. S. Kim, D. Kim, H. Shinokubo, and A. Osuka
  • Journal Title: Angew. Chem. Int. Ed. 47 Pages: 6004-6007
  • Peer Reviewed
• [Journal Article] A meso-meso Directly Linked Octameric Porphyrin Square (2008)
  • Author(s): N. Aratani and A. Osuka
  • Journal Title: Chem. Commun Pages: 4067-4069
  • Peer Reviewed
• [Presentation] Development of large photofunctionalπ-conjugated systems (2010)
  • Author(s): Naoki Aratani
  • Organizer: International Symposium on Chemical Conversion of Light Energy
  • Place of Presentation: 近畿大学(大阪)
  • Year and Date: 2010-03-29
• [Presentation] 構造の明確な巨大ポルフィリンアレイの構築 (2010)
  • Author(s): 荒谷直樹
  • Organizer: 日本化学会第90春季年会
  • Place of Presentation: 近畿大学 (大阪)
  • Year and Date: 2010-03-28
• [Presentation] Development of large photofunctional π-conjugated systems (2010)
  • Author(s): Naoki Aratani
  • Organizer: International Symposium on Chemical Conversion of Light Energy
  • Place of Presentation: 近畿大学 (大阪)
  • Year and Date: 2010-03-28
• [Presentation] Electronically Interactive Giant Porphyrin Arrays (2010)
  • Author(s): Naoki Aratani
  • Organizer: Kyushu University Global COE Program The 10th International Workshop "Science for Future Molecular Systems "招待講演
  • Place of Presentation: Kyushu University(福岡)
  • Year and Date: 2010-02-19
• [Presentation] Electronically Interactive Giant Porphyrin Arrays (2010)
  • Author(s): Naoki Aratani
  • Organizer: Kyushu University Global COE Program The 10th International Workshop "Science for Future Molecular Systems"
  • Place of Presentation: Kyushu University (福岡)
  • Year and Date: 2010-02-19
• [Presentation] 構造の明確な巨大ポルフィリンアレイの構築 (2010)
  • Author(s): 荒谷直樹
  • Organizer: (若い世代の特別講演)日本化学会第90春季年会
  • Place of Presentation: 近畿大学(大阪)
• [Presentation] 巨大分子の有機合成 (2009)
  • Author(s): 荒谷直樹
  • Organizer: 第5回有機元素化学セミナー
  • Place of Presentation: 京都大学宇治キャンパス木質ホール
  • Year and Date: 2009-02-19
• [Presentation] Electronically Interactive Giant Porphyrin Arrays (2009)
  • Author(s): Naoki Aratani
  • Organizer: JSPS Asian CORE Program China - Japan Joint Symposium招待講演
  • Place of Presentation: Sapporo
• [Presentation] Synthesis of Large Oligoacenequinones (2009)
  • Author(s): Naoki Aratani, Ryotaro Aso, Atsuhiro Osuka
  • Organizer: 13th International Symposium on Novel Aromatic Compounds
  • Place of Presentation: Luxembourg
• [Presentation] ノナセンキノンの合成・物性とその反応性(1) (2009)
  • Author(s): 麻生亮太郎・荒谷直樹・大須賀篤弘
  • Organizer: 第89日本化学会春季年会
  • Place of Presentation: 日大理工学部船橋キャンパス
• [Presentation] ノナセンキノンの合成・物性とその反応性(2) (2009)
  • Author(s): 荒谷直樹・麻生亮太郎・大須賀篤弘
  • Organizer: 第89日本化学会春季年会
  • Place of Presentation: 日大理工学部船橋キャンパス
• [Presentation] 巨大分子の有機合成 (2009)
  • Author(s): 荒谷直樹
  • Organizer: 第五回有機元素化学シンポジウム(招待講演)
  • Place of Presentation: 京都大学大学宇治キャンパス木質ホール
• [Presentation] ノナセンキノンの合成・物性とその反応性(2) (2009)
  • Author(s): 荒谷直樹、麻生亮太郎、大須賀篤弘
  • Organizer: 日本化学会第89春季年会
  • Place of Presentation: 日本大学理工学部船橋キャンパス
• [Presentation] 構造の明確な巨大分子を創る (2008)
  • Author(s): 荒谷直樹
  • Organizer: グローバルCOE有機若手ワークショップ(招待講演)
  • Place of Presentation: 京都大学大学院理学研究科2号館120号室
• [Presentation] Synthesis of phenylene-linked porphyrin arrays by Pd-catalyzed coupling reaction (2008)
  • Author(s): Naoki Aratani, Atsuhiro Osuka
  • Organizer: International Symposium on Porphyrins and Phthalocyanines
  • Place of Presentation: Moscow, Russia
• [Presentation] Synthesis of phenylene-linked porphyrin arrays by Pdcatalyzed coupling reaction (2008)
  • Author(s): N. Aratani and A. Osuka
  • Organizer: Fifth International Conference on Porphyrifis and Phthalocyanines (ICPP-5)
  • Place of Presentation: Moscow, Russia
• [Presentation] 構造の明確な巨大分子を創る (2008)
  • Author(s): 荒谷直樹
  • Organizer: 京都大学グローバルCOEプログラム「物質科学の新基盤構築と次世代育成国際拠点」グローバルCOE有機若手ワークショップ
  • Place of Presentation: 京都大学理学部
• [Book] 配位空間の化学・第IV編第3章・自己識別会合(北川進監修) (2009)
  • Author(s): 荒谷直樹・大須賀篤弘
  • Publisher: CMC出版
• [Remarks]
  • URL: http://kuchem.kyoto-u.ac.jp/shuyu/j/aratani.html