Novel Porphyrinoids and Construction of π-Space based on their Assemblies

2012 Fiscal Year Final Research Report

• Project Area: Emergence of highly elaborated pai-space and its function
• Project/Area Number: 20108006
• Research Category: Grant-in-Aid for Scientific Research on Innovative Areas (Research in a proposed research area)
• Allocation Type: Single-year Grants
• Review Section: Science and Engineering
• Research Institution: Kyoto University
• Principal Investigator: OSUKA Atsuhiro 京都大学, 大学院・理学研究科, 教授 (80127886)
• Project Period (FY): 2008 – 2012
• Keywords: ポルフィリン / 2光子吸収 / サブポルフィリン / ポルフィリンテープ

Research Abstract

We've developed a variety of fused porphyrinoids and porphyrin arrays and revealed their structure-TPA property relationships. In addition, novel conjugated porphyrinoids have been synthesized based on expanded porphyrin frameworks.

Research Products

• [Journal Article] A Moebius Antiaromatic Complex as a Kinetically Controlled Product in Phosphorus Insertion to a [32]Heptaphyrin (2012)
  • Author(s): Higashino, T. ; Lee, B. S. ; Lim, J. M. ; Kim, D. ; Osuka, A
  • Journal Title: Angew. Chem. Int. Ed Volume: 51 Pages: 13105-13108
  • DOI: DOI:10.1002/anie.201208147
  • Peer Reviewed
• [Journal Article] Effective meso Fabrications of Subporphyrins (2012)
  • Author(s): Kitano, M.; Hayashi, S.; Tanaka, T.; Yorimitsu, H.; Aratani, N.; Osuka, A
  • Journal Title: Angew. Chem. Int. Ed. Pages: 5593-5597
  • DOI: DOI:10.1002/anie.201201853
  • Peer Reviewed
• [Journal Article] Hexaphyrin Fused to Two Anthracenes (2012)
  • Author(s): Naoda, K. ; Mori, H. ; Aratani, N. ; Lee, B. S. ; Kim, D. Osuka, A
  • Journal Title: Angew. Chem. Int. Ed Volume: 51 Pages: 9856-9859
  • DOI: DOI:10.1002/anie.201204446
  • Peer Reviewed
• [Journal Article] Porphyrin-hexaphyrin hybrid tapes (2012)
  • Author(s): Tanaka, T.; Aratani, N.; Lim, J. M.; Kim, K. S.; Kim, D.; Osuka, A
  • Journal Title: Chem. Sci Volume: 2 Pages: 1414-1418
  • DOI: DOI:10.1039/C1SC00228G
  • Peer Reviewed
• [Journal Article] Planar Subporphyrin Borenium Cations (2011)
  • Author(s): Tsurumaki, E.; Hayashi, S.; Tham, F.S.; Reed, C.A.; Osuka, A
  • Journal Title: J. Am. Chem. Soc Volume: 133 Pages: 11956-11959
  • DOI: DOI:10.1021/ja2056566
  • Peer Reviewed
• [Journal Article] Synthesis and Properties of Boron(III)-Coordinated Subbacteriochlorins (2011)
  • Author(s): Hayashi, S.; Tsurumaki, E.; Inokuma, Y.; Kim, P.; Sung, Y. M.; Kim, D.; Osuka, A
  • Journal Title: J. Am. Chem. Soc Volume: 133 Pages: 4254-4256
  • DOI: DOI:10.1021/ja200669a
  • Peer Reviewed
• [Journal Article] Palladium-Catalyzed β-Selective Direct Arylation of Porphyrins (2011)
  • Author(s): Kawamata, Y.; Tokuji, S.; Yorimitsu, H.; Osuka, A
  • Journal Title: Angew. Chem., Int. Ed Volume: 50 Pages: 8867-8870
  • DOI: DOI:10.1002/anie.201102318
  • Peer Reviewed
• [Journal Article] eutral Radical and Singlet Biradical Forms of Meso-Free, -Keto, and -Diketo Hexaphyrins(1.1.1.1.1.1): Effects on Aromaticity and Photophysical Properties (2011)
  • Author(s): Ishida, M.; Shin, J.-Y.; Lim, J.M.; Lee,B.S.; Yoon,M.-C.; Koide,T,; Sessler, J.; Osuka, A.; Kim,D,
  • Journal Title: J. Am. Chem. Soc Volume: 133 Pages: 15533-15544
  • DOI: DOI:10.1021/ja204626t
  • Peer Reviewed
• [Journal Article] A Porphyrin Nanobarrel That Encapsulates C60 (2010)
  • Author(s): Song, J.; Aratani, N.; Shinokubo, H.; Osuka, A
  • Journal Title: J. Am. Chem. Soc Pages: 16356-16357
  • DOI: DOI:10.1021/ja107814s
  • Peer Reviewed
• [Journal Article] A Stable Organic Radical Delocalized on Highly Twisted π System Formed Upon Palladium Metalation of A Moebius Aromatic Hexaphyrin (2010)
  • Author(s): Rath, H.; Tokuji, S.; Aratani, N.; Furukawa, K.; Lim, J. M.; Kim, D.; Shinokubo, H.; Osuka, A
  • Journal Title: Angew. Chem. Int. Ed Volume: 49 Pages: 1489-1491
  • DOI: DOI:10.1002/anie.200906017
  • Peer Reviewed
• [Journal Article] A Stable Non-Kekul Singlet Biradicaloid from meso-Free 5,10,20,25-Tetrakis(Pentafluorophenyl)-Substituted [26]Hexaphyrin(1.1.1.1.1.1) (2010)
  • Author(s): Koide, T.; Furukawa, K.; Shinokubo, H.; Shin, J.-Y.; Kim, K. S.; Kim, D.; Osuka, A
  • Journal Title: J. Am. Chem. Soc Volume: 132 Pages: 7246-7247
  • DOI: DOI:10.1021/ja101040s
  • Peer Reviewed
• [Journal Article] Moebius Antiaromatic Bisphosphorus Complexes of [30]Hexaphyrins (2010)
  • Author(s): Higashino, T.; Lim, J. M.; Miura, T.; Saito, S.; Shin, J.-Y.; Kim, D.; Osuka, A
  • Journal Title: Angew. Chem. Int. Ed Volume: 49 Pages: 4950-4954
  • DOI: DOI:10.1002/anie.201001765
  • Peer Reviewed
• [Journal Article] Metal Complexes of Chiral Moebius Aromatic [28]Hexaphyrin(1.1.1.1.1.1): Enantiomeric Separation, Absolute Stereochemistry, and Asymmetric Synthesis (2010)
  • Author(s): Tanaka, T.; Sugita, T.; Tokuji, S.; Saito, S.; Osuka, A
  • Journal Title: Angew. Chem. Int. Ed Pages: 6619-6621
  • DOI: DOI:10.1002/anie.201002282
  • Peer Reviewed
• [Journal Article] Fully π-Conjugated Helices from Oxidative Cleavage of meso-Aryl-Substituted Expanded Porphyrins (2010)
  • Author(s): Saito, S.; Furukawa, K.; Osuka, A
  • Journal Title: J. Am. Chem. Soc Volume: 132 Pages: 2128-2129
  • DOI: DOI:10.1021/ja909929s
  • Peer Reviewed
• [Journal Article] T-shaped Three-Coordinate Copper(II) Heptaphyrin Complexes (2009)
  • Author(s): Saito, S.; Furukawa, K.; Osuka, A
  • Journal Title: Angew. Chem. Int. Ed Volume: 48 Pages: 8086 -8089
  • DOI: DOI:10.1002/anie.200902901
  • Peer Reviewed
• [Journal Article] 2,5-Thionylene-Bridged Triangular and Linear Porphyrin Trimers (2008)
  • Author(s): Song, J.; Jang, S. Y.; Yamaguchi, S.; Sankar, J.; Hiroto, S.; Aratani, N.; Shin, J.-Y.; Easwaramoorthi, S.; Kim, K. S.; Kim, D.; Shinokubo, H.; Osuka, A
  • Journal Title: Angew. Chem. Int. Ed Volume: 47 Pages: 6004-6007
  • DOI: DOI:10.1002/anie.200802026
  • Peer Reviewed
• [Journal Article] Protonation-Triggered Conformational Changes to Moebius Aromatic [32] Heptaphyrins(1.1.1.1.1.1.1) (2008)
  • Author(s): Saito, S.; Shin, J.-Y.; Lim, J. M.; Kim, K. S.; Kim, D.; Osuka, A
  • Journal Title: Angew. Chem., Int. Ed Volume: 47 Pages: 9657-9660
  • DOI: DOI:10.1002/anie.200804457
  • Peer Reviewed
• [Journal Article] Two-Dimensionally Extended Porphyrin Tapes: Synthesis and Shape-Dependent Two-Photon Absorption Properties (2008)
  • Author(s): Nakamura, Y.; Jang, S. Y.; Tanaka, T.; Aratani, N.; Lim, J. M.; Kim, K. S.; Kim, D.; Osuka, A
  • Journal Title: Chem. Eur. J Volume: 14 Pages: 8279-8289
  • DOI: DOI:10.1002/chem.200800776
  • Peer Reviewed
• [Presentation] Catalytic Selective Direct Arylation of Porphyrin Periphery (2012)
  • Author(s): Hideki Yorimitsu, Atsuhiro Osuka
  • Organizer: 7th International Conference on Porphyrins and Phthalocyanines
  • Place of Presentation: 韓国 済州島
  • Year and Date: 20120701-06
• [Presentation] パラジウム(II)錯化によるヘプタフィリンのN-混乱ポルフィリン骨格を有する錯体への転位反応 (2011)
  • Author(s): 米田友貴・斎藤尚平・依光英樹・大須賀篤弘
  • Organizer: 第22回 基礎有機化学討論会
  • Place of Presentation: つくば国際会議場
  • Year and Date: 20110921-23
• [Presentation] Mobius Aromaticity in Expanded Porphyrins (2010)
  • Author(s): Atsuhiro Osuka
  • Organizer: Pacifichem 2010
  • Place of Presentation: Honolulu, Hawaii
  • Year and Date: 20101215-20
• [Presentation] 新しいポルフィリノイドの化学をめざして (2010)
  • Author(s): 大須賀篤弘
  • Organizer: 第21回基礎有機化学討論会
  • Place of Presentation: 名古屋大学
  • Year and Date: 20100909-11
• [Presentation] Synthesis of Novel Subporphyrins and Related Molecules (2010)
  • Author(s): Atsuhiro Osuka
  • Organizer: Sixth International Conference on Porphyrins and Phthalocyanines (ICPP-6)
  • Place of Presentation: New Mexico, USA
  • Year and Date: 20100704-09
• [Presentation] Porphyrinoids with Large Two-Photon Absorption Cross-Section (2010)
  • Author(s): Atsuhiro Osuka
  • Organizer: International Symposium on Supramolecular Chemistry Kangwon
  • Place of Presentation: Korea
  • Year and Date: 2010-10-06
• [Presentation] Exploration of Novel Porphyrinoids with Large Two-Photon Absorption Cross Sections (2010)
  • Author(s): Atsuhiro Osuka
  • Organizer: Organic Materials Chemistry and Molecular Design and Synthesis Meeting
  • Place of Presentation: Wasignton, USA
  • Year and Date: 2010-09-21
• [Remarks]
  • URL: http://kuchem.kyoto-u.ac.jp/shuyu