Preparation and properties of 2D honeycomb carbon materials

• Project/Area Number: 16K14064
• Research Category: Grant-in-Aid for Challenging Exploratory Research
• Allocation Type: Multi-year Fund
• Research Field: Organic and hybrid materials
• Research Institution: Osaka University
• Principal Investigator: KUBO Takashi 大阪大学, 理学研究科, 教授 (60324745)
• Project Period (FY): 2016-04-01 – 2018-03-31
• Project Status: Completed (Fiscal Year 2017)
• Budget Amount: ¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000); Fiscal Year 2017: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000); Fiscal Year 2016: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
• Keywords: トリナフトプロペラン / ハニカム二次元炭素物質 / 一次元鎖 / 原子間力顕微鏡 / 電子移動反応 / 二次元ポリマー / 炭素材料 / ハニカム構造 / 二次元物質 / 三回対称 / 芳香族化合物

Outline of Final Research Achievements

In this study we prepared a hexabromo derivative (1) of a propeller-shaped polycyclic aromatic hydrocarbon as a component of honeycomb two-dimensional carbon materials, and also attempted to prepare honeycomb carbon materials on metal surfaces. Firstly, we succeeded in the improvement of synthetic yield of the hexabromo derivative from 20% to 40%. Subsequently, when the polymerization reaction of 1 was carried out on a metal substrate, it was found that 1 was adsorbed in a form as if standing on the substrate, furthermore, it was found that the polymerization reaction proceeded further, giving a one-dimensional chain. In addition, we succeeded in π expansion of 1 , and also determined the rate of electron hopping between the blades of the propeller-shaped molecule and directly observed hydrogen atoms by atomic force microscopy measurements.

Research Products

• [Journal Article] Direct Quantitative Measurement of the C=O・・・H-C Bond by Atomic Force Microscopy (2017)
  • Author(s): Kawai, Shigeki; Nishiuchi, Tomohiko; Kodama, Takuya; Spijker, Peter; Pawlak, Remy; Meier, Tobias; Tracey, John; Kubo, Takashi; Meyer, Ernst; Foster, Adam S.
  • Journal Title: Sci. Adv. Volume: 3 Issue: 5
  • DOI: 10.1126/sciadv.1603258
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Elucidation of Intramolecular Through‐Space Electronic Communication in Propeller‐Shaped Molecule (2017)
  • Author(s): Takuya Kodama, Yasukazu Hirao, Tomohiko Nishiuch, Takashi Kubo
  • Journal Title: ChemPlusChem Volume: 印刷中 Issue: 7 Pages: 1006-1009
  • DOI: 10.1002/cplu.201700045
  • Peer Reviewed
• [Presentation] Elucidation of the Through-Space Spin Delocalization Mode of Phenalenyl-Fused [3.3.3]Propellane (2017)
  • Author(s): Takuya KODAMA, Yasukazu HIRAO, Tomohiko, NISHIUCHI, Takashi KUBO
  • Organizer: 日本化学会 第97春季年会
  • Place of Presentation: 慶應義塾大学
  • Year and Date: 2017-03-16
• [Presentation] Spin Distribution of Multi-Phenalenyl Radicals (2017)
  • Author(s): Takashi Kubo
  • Organizer: International Symposium on Reactive Intermediates and Unusual Molecules (ISRIUM)
  • Int'l Joint Research / Invited
• [Presentation] Spin-Spin Interaction of Multi-Phenalenyl Radicals (2017)
  • Author(s): Takuya Kodama and Takashi Kubo
  • Organizer: 8th Pacific Symposium on Radical Chemistry
  • Int'l Joint Research / Invited
• [Presentation] Spin Distribution of Multi-Phenalenyl Radicals (2017)
  • Author(s): Takashi Kubo
  • Organizer: 17th International Symposium on Novel Aromatic Compounds
  • Int'l Joint Research / Invited
• [Presentation] Synthesis and Properties of Phenalenyl Based Propellar Shaped Hydrocarbon Radical (2016)
  • Author(s): Takuya KODAMA, Yasukazu HIRAO, Tomohiko, NISHIUCHI, Takashi KUBO
  • Organizer: The 15th International Conference on Molecule-Based Magnets (ICMM2016)
  • Place of Presentation: 仙台国際センター
  • Year and Date: 2016-09-04
• [Presentation] Synthesis and Properties of Through-Space Conjugated Phenalenyl Radical (2016)
  • Author(s): Takuya KODAMA, Yasukazu HIRAO, Tomohiko, NISHIUCHI, Takashi KUBO
  • Organizer: Workshop on New π-Electronic Systems: Theory and Experiments
  • Place of Presentation: 大阪大学