Synthesis of boron-containing buckybowl

2021 Fiscal Year Final Research Report

• Project/Area Number: 19K22184
• Research Category: Grant-in-Aid for Challenging Research (Exploratory)
• Allocation Type: Multi-year Fund
• Review Section: Medium-sized Section 33:Organic chemistry and related fields
• Research Institution: Kyoto University
• Principal Investigator: Hiroto Satoru 京都大学, 人間・環境学研究科, 准教授 (30547427)
• Project Period (FY): 2019-06-28 – 2022-03-31
• Keywords: アザバッキーボウル / 曲面π共役分子 / ホウ素

Outline of Final Research Achievements

π-conjugated molecules usually have a planar structure. We have reported the synthesis of a new π-conjugated molecule, azabuckybowl, which has a curved structure and contains a hetero atom inside. Based on the knowledge obtained from its synthesis, we attempted to synthesize a borabuckybowl, which has been considered to be the most difficult to synthesize. In the process, they succeeded in synthesizing azabuckybowl-PBI complexes that exhibit intramolecular charge transfer, and found results suggesting the construction of an unusual stacking structure in which curved surfaces and planes are stacked on top of each other. Furthermore, a novel synthetic method for terphenyl derivatives, which are precursors for borabuckybowl synthesis, was successfully developed.

Free Research Field

構造有機化学

Academic Significance and Societal Importance of the Research Achievements

曲面構造をもつπ共役分子は古くから合成が行われているが、多くは炭素または水素原子のみで構成されており、ヘテロ元素を含むものはほとんどない。合成において、ヘテロ元素が脱離しやすい、空気酸化や水分の影響を受けて壊れてしまう点が問題であった。今回、その中で最難関のホウ素を含む曲面分子の合成に挑んだ。その結果、有用な前駆体の合成に成功した。さらに、目的化合物の機能発現のモデルとなる分子を合成し、有機エレクトロニクスデバイスに応用可能な新規な知見を得ることに成功した。これらの成果はこれまで応用が不明瞭であった曲面分子の可能性を広げるものであり、新たな有機材料の創出につながる重要な成果である。