Exploration of Antiaromatic Stacking and Preparation of Antiaromatic Liquid Crystals

• Project/Area Number: 25620030
• Research Category: Grant-in-Aid for Challenging Exploratory Research
• Allocation Type: Multi-year Fund
• Research Field: Organic chemistry
• Research Institution: Nagoya University
• Principal Investigator: SHINOKUBO Hiroshi 名古屋大学, 工学(系)研究科(研究院), 教授 (50281100)
• Project Period (FY): 2013-04-01 – 2015-03-31
• Project Status: Completed (Fiscal Year 2014)
• Budget Amount: ¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000); Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000); Fiscal Year 2013: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
• Keywords: 反芳香族 / ポルフィリン / ノルコロール / スタッキング / 液晶 / 求核置換反応 / 直接官能基化 / パイ電子 / 二次電池 / リチウム電池

Outline of Final Research Achievements

Norcorrole Ni(II) complex is a strongly antiaromatic porphyrin analogue, which is enough stable to handle in air. In this research, we prepared norcorrole Ni(II) complexes with various substituents and investigated their structures in the solid state.

Research Products

• [Journal Article] Photodynamics of [26]- and [28]Hexaphyrin-Bodipy Hybrids (2014)
  • Author(s): J.-Y. Shin, K. Kim, J. M. Lim, T. Tanaka, D. Kim, K. Kim, H. Shinokubo, and A. Osuka
  • Journal Title: Chem. Eur. J. Volume: 20 Issue: 16 Pages: 4574-4582
  • DOI: 10.1002/chem.201400315
  • Peer Reviewed / Open Access
• [Journal Article] Synthesis of Curved Hexa-peri-hexabenzocoronenes (2014)
  • Author(s): Ryuichi Yamaguchi, Satoru Hiroto, Hiroshi Shinokubo
  • Journal Title: Chemistry Letters Volume: 43 Issue: 10 Pages: 1637-1639
  • DOI: 10.1246/cl.140577
  • NAID: 130004693827
  • Peer Reviewed / Open Access / Acknowledgement Compliant
• [Journal Article] An Antiaromatic Electrode-Active Material Enabling High Capacity and Stable Performance of Rechargeable Batteries (2014)
  • Author(s): J.-Y. Shin, T. Yamada, H. Yoshikawa, K. Awaga, and H. Shinokubo
  • Journal Title: Angew. Chem. Int. Ed Volume: 53 Issue: 12 Pages: 3096-3101
  • DOI: 10.1002/anie.201310374
  • Peer Reviewed / Open Access
• [Journal Article] Near-IR Absorbing Nickel(II) Porphyrinoids Prepared by Regioselective Insertion of Silylenes into Antiaromatic Nickel(II) Norcorrole (2014)
  • Author(s): Takaki Fukuoka, Kenya Uchida, Young Mo Sung, Ji-Young Shin, Shintaro Ishida, Dr. Jong Min Lim, Satoru Hiroto, Ko Furukawa, Dongho Kim, Takeaki Iwamoto, Hiroshi Shinokubo
  • Journal Title: Angewandte Chemie, International Edition Volume: 53 Issue: 6 Pages: 1506-1509
  • DOI: 10.1002/anie.201309921
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Porphyrin Derivatives with Carbon-Metal Bonds (2009)
  • Author(s): H. Shinokubo
  • Journal Title: Journal of Synthetic Organic Chemistry, Japan Volume: 67 Issue: 7 Pages: 688-700
  • DOI: 10.5059/yukigoseikyokaishi.67.688
  • NAID: 10025399184
  • ISSN: 0037-9980, 1883-6526
  • Peer Reviewed
• [Presentation] 反芳香族ノルコロールニッケルの位置選択的な直接官能基化 (2015)
  • Author(s): 野澤 遼，山本 恵太郎，辛 知映，廣戸 聡，忍久保 洋
  • Organizer: 日本化学会第95春季年会
  • Place of Presentation: 船橋
  • Year and Date: 2015-03-26
• [Presentation] 有機反応化学とポルフィリン化学の接点を求めて (2014)
  • Author(s): 忍久保 洋
  • Organizer: 有機合成化学協会東海支部総合講演会
  • Place of Presentation: 静岡
  • Year and Date: 2014-12-13
  • Invited
• [Presentation] Synthesis, Property, and Reactivity of Norcorrole Ni(II) Complex (2014)
  • Author(s): 忍久保 洋
  • Organizer: Michinoku International Symposium on Porphyrins, Phthalocyanines and Functional π Molecules
  • Place of Presentation: 蔵王
  • Year and Date: 2014-10-13
• [Presentation] 有機反応化学とポルフィリン化学の接点を求めて (2014)
  • Author(s): 忍久保 洋
  • Organizer: 愛媛大学大学院理工学研究科講演会
  • Place of Presentation: 松山
  • Year and Date: 2014-09-26
  • Invited
• [Presentation] ノルコロールの反応性に関する研究 (2014)
  • Author(s): 野澤 遼，山本 恵太郎，福岡 嵩規，辛 知映，廣戸 聡，忍久保 洋
  • Organizer: 第２５回基礎有機化学討論会
  • Place of Presentation: 仙台
  • Year and Date: 2014-09-08
• [Presentation] ジピリン金属錯体を用いた[32]オクタフィリン金属錯体の合成および物性 (2014)
  • Author(s): 木戸 裕允，辛 知映，忍久保 洋
  • Organizer: 第２５回基礎有機化学討論会
  • Place of Presentation: 仙台
  • Year and Date: 2014-09-08
• [Presentation] ノルコロールの反応性に関する研究 (2014)
  • Author(s): 野澤 遼，山本 恵太郎，福岡 嵩規，辛 知映，廣戸 聡，忍久保 洋
  • Organizer: 第４６回構造有機若手の会
  • Place of Presentation: 池田
  • Year and Date: 2014-08-08
• [Presentation] 有機反応化学とポルフィリン化学の接点を求めて (2014)
  • Author(s): 忍久保 洋
  • Organizer: 岡山大学大学院理学研究科講演会
  • Place of Presentation: 岡山
  • Year and Date: 2014-07-31
  • Invited
• [Presentation] Synthesis, Property, Reactivity, and Assembly of Norcorrole Ni(II) Complexes (2014)
  • Author(s): 忍久保 洋
  • Organizer: 8th International Conference on Porphyrins and Phthalocyanines (ICPP-8)
  • Place of Presentation: Istanbul
  • Year and Date: 2014-06-27
  • Invited
• [Presentation] ジピリンからポルフィリンへ： ポルフィリン類縁体の新合成法の開発 (2014)
  • Author(s): 忍久保 洋
  • Organizer: 九州大学先導物質化学研究所講演会
  • Place of Presentation: 福岡
  • Invited
• [Presentation] 反芳香族性ノルコールニッケル錯体の還元反応に関する研究 (2014)
  • Author(s): 山本 恵太郎
  • Organizer: 第９４回 日本化学会春季年会
  • Place of Presentation: 名古屋
• [Presentation] 有機金属化学的手法による新規ポルフィリン類縁体の合成 (2013)
  • Author(s): 忍久保 洋
  • Organizer: 第103回有機合成シンポジウム
  • Place of Presentation: 東京
  • Invited
• [Presentation] Organometallic Route to Novel Porphyrins (2013)
  • Author(s): H. Shinokubo
  • Organizer: Lecture at National University of Singapore
  • Place of Presentation: Singapore
  • Invited
• [Presentation] Synthesis and Properties of a Stable Antiaromatic Porphyrinoid "Norcorrole" (2013)
  • Author(s): H. Shinokubo
  • Organizer: 15th Asian Chemical Congress (15ACC)
  • Place of Presentation: Singapore
  • Invited
• [Presentation] meso置換反芳香族性ノルコロールの合成と物性 (2013)
  • Author(s): 木戸 裕允
  • Organizer: 第28回基礎有機化学討論会
  • Place of Presentation: 東京
• [Presentation] 反芳香族性ノルコロールとカルベンの反応 (2013)
  • Author(s): 福岡嵩規
  • Organizer: 第24回基礎有機化学討論会
  • Place of Presentation: 東京
• [Remarks] 忍久保研究室ホームページ
  • URL: http://www.apchem.nagoya-u.ac.jp/hshino/top.html
• [Remarks] 名古屋大学プレスリリース
  • URL: http://www.nagoya-u.ac.jp/about-nu/public-relations/researchinfo/upload_images/20140220_eng.pdf