Aromatic architect: design of structures and spaces created by pi-conjugated systems and developments of their functions

2023 Fiscal Year Final Research Report

• Project/Area Number: 20H02721
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Review Section: Basic Section 33010:Structural organic chemistry and physical organic chemistry-related
• Research Institution: Tokyo Institute of Technology
• Principal Investigator: Toyota Shinji 東京工業大学, 理学院, 教授 (80207646)
• Project Period (FY): 2020-04-01 – 2024-03-31
• Keywords: 芳香環 / 構造空間設計 / 大環状分子 / らせん分子 / パイ共役系化合物 / ホストーゲスト / ケージ分子 / キラル光学特性

Outline of Final Research Achievements

We studied macrocyclic and helical-shaped pi-conjugated compounds based on the concept of “aromatic architect,” to created new chemical substances by designing structures and spaces from aromatic units.
For the macrocyclic compounds, ring and cage molecules were synthesized using various anthracene units. We revealed that the cages included fullerene guests more strongly than the rings, and that the guest molecules exhibited rotational behavior in the cages. For the helical compounds, novel expanded helicenes were synthesized by fusing up to five anthracene units, and their structures and properties were investigated. The enantiomers of some derivatives were resolved, and showed characteristic chiroptical properties.

Free Research Field

構造有機化学

Academic Significance and Societal Importance of the Research Achievements

大環状化合物では，芳香族ユニットからなるリングやケージが炭素に結合した水素とパイ電子間の相互作用を推進力としてフラーレンゲストを包接することを明らかにした．らせん化合物では，高度に巻いた拡張ヘリセン誘導体の合成およびエナンチオマーの分割に成功した．これらの成果は構造有機化学や超分子化学の分野において，グラフェン関連の多環式芳香族化合物の構造や物性を理解するために学術的に重要であり，新しい分子設計の指針を示したものとして意義がある．