Development functional materials by the boron-mediated aromatic ring-forming reactions

2019 Fiscal Year Final Research Report

• Project/Area Number: 17H03020
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Organic chemistry
• Research Institution: Tokyo Institute of Technology
• Principal Investigator: Shoji Yoshiaki 東京工業大学, 科学技術創成研究院, 准教授 (40525573)
• Project Period (FY): 2017-04-01 – 2020-03-31
• Keywords: ホウ素 / π電子系分子 / π共役高分子 / ルイス酸 / アルキン / 固体物性

Outline of Final Research Achievements

In this research, we focused on (1) the elucidation of the mechanism of a new boron-mediated aromatic ring construction reaction and (2) the development of π-conjugated functional materials. Through experimental and theoretical studies, we succeeded in the evaluation of the boron-mediated 1,2-carboboration of alkynes　and the oxidative deborylation/C-C coupling of the resultant borepin derivatives. We also clarified the structural elements of 9-borafluorenes required for the efficient benzannulation of alkyne derivatives. Using the optimized reaction conditions and substrates, we have developed a dynamic propeller molecule with superb chiral sensing capability and a direct transformation reaction of linear π-conjugated polymers into microporous zigzag-shaped polymers. These findings would be useful for the development of new π-conjugated materials with unique structural and dynamic properties.

Free Research Field

有機典型元素化学

Academic Significance and Societal Importance of the Research Achievements

本研究では、独自に見出した、ホウ素化合物による新しいπ電子系骨格構築反応のメカニズムを明らかにするとともに、開発した新反応を用いて、特異な構造特性や動的特性を有するπ電子系機能分子・高分子を開発しました。本研究を通じて、典型元素であるホウ素が織りなす新たな反応化学を開拓することができました。また得られた知見は、有機エレクトロニクスに応用可能な新材料開発にも有用であると期待できます。