Development of Azahelicene-Based Chiroptical Materials

2023 Fiscal Year Final Research Report

• Project/Area Number: 21K05039
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Review Section: Basic Section 33010:Structural organic chemistry and physical organic chemistry-related
• Research Institution: Okayama University
• Principal Investigator: Maeda Chihiro 岡山大学, 環境生命自然科学学域, 助教 (80581371)
• Project Period (FY): 2021-04-01 – 2024-03-31
• Keywords: ヘリセン / カルバゾール / 円偏光発光 / ホストゲスト

Outline of Final Research Achievements

Helicenes, ortho-fused polycyclic aromatic hydrocarbons, have been recognized as promising CPL dyes. However, the synthetic difficulty and tediousness have often been problems, and only small amounts of optically pure helicenes have been obtained by using chiral HPLC in most cases. Herein, aza[7]helicenes with (1R)-menthyl substituents were synthesized via the intramolecular Scholl reaction, and the diastereomeric pairs were separated by silica gel column chromatography. The optically pure helicenes were further transformed into the corresponding cyclic dimers, which showed the high CPL brightness and selective recognition of a fluoride ion.

Free Research Field

構造有機化学

Academic Significance and Societal Importance of the Research Achievements

我々はジアステレオマー法を用いて光学活性なアザヘリセンの合成を行った。このアザヘリセンはキラルなカルバゾールであり、今後様々なキラル光学材料への貢献が期待される。またキラルなマクロサイクルを用いた選択的なフッ化物イオン認識は色調の大きな変化を伴い、キラルセンサーとしての機能を有する。本研究で見出した新しい知見は、我々だけでなく他の研究者の今後の研究の推進にも貢献すると期待される。