C-H Bond transformations for n-type semiconductors of functional fullerenes and fullerene segments(Fostering Joint International Research)

2018 Fiscal Year Final Research Report

• Project/Area Number: 15KK0180
• Research Category: Fund for the Promotion of Joint International Research (Fostering Joint International Research)
• Allocation Type: Multi-year Fund
• Research Field: Synthetic chemistry
• Research Institution: Tohoku University
• Principal Investigator: JIN Tienan 東北大学, 理学研究科, 准教授 (80431493)
• Research Collaborator: Bao Ming 大連理工大学, 精細化工国家重点実験室, 教授
• Project Period (FY): 2016 – 2018
• Keywords: π拡張縮環骨格 / 官能基化フラーレン / 一電子酸化反応 / C-H結合変換 / フラーレン部分骨格

Outline of Final Research Achievements

The selective monocyclization of Cationic Lithium Endohedral Fullerene with dibromide in the presence of manganese powder has been studied. The selective cyclotrimerization of 5-bromothiazole through sequential C-H bond functionalization has been developed in the presence of Pd(II) catalyst toward synthesis of novel star-shaped π-extended benzotristhiazoles. The biphenyl-tethered ortho-alkynylanilines undergo the tandem cyclization through Pd(II)-catalyzed C-N/ortho-C-H bond cleavage to give the corresponding dibenzo[a,c]carbazoles effectively. A novel FeCl3-mediated oxidative spirocyclization for construction of a new class of dispirolinked π-conjugated molecules, dispiro[fluorene-9,5'-indeno[2,1-a]indene-10',9''fluorene]s (DSFIIFs), has been developed. A highly efficient single electron oxidative spirocyclization and 1,2-aryl migration tandem synthetic method for the construction of extended polyaromatic hydrocarbons (PAHs) has been developed.

Free Research Field

有機合成化学

Academic Significance and Societal Importance of the Research Achievements

本研究は、新規フラーレンの官能基化およびフラーレン部分骨格の構築に関する基礎研究と物質応用研究との連係による相乗効果を発揮させ、研究活動の実績を積み上げるとともに、国際的な緊密な研究交流を通じて信頼関係を築くことと、日本の高い学術的国際性を世界に示すところに意義がある。また、共同研究交流を通して、高いレベルの論文の研究成果を産出し、日本と中国の将来を担う若手研究者の交流を促進し、相手国の人材養成や基礎研究の振興に貢献するところに社会的意義がある。