Development of unique pai-conjugated smart materials based on the catalytic and regioselective functionalization of azulenes

2019 Fiscal Year Final Research Report

• Project/Area Number: 16K05778
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Synthetic chemistry
• Research Institution: Okayama University
• Principal Investigator: Murai Masahito 岡山大学, 自然科学研究科, 助教 (40647070)
• Project Period (FY): 2016-04-01 – 2020-03-31
• Keywords: アズレン / 多環芳香族炭化水素 / 双極子 / フェナセン / アリール化

Outline of Final Research Achievements

Uniquely polarized hydrocarbon, azulene, possesses unusual photophysical and electrochemical properties that are unique for small molecules without any hetero atoms. The main purpose of the present study is development of a regioselective functionalization methods to further extend and disclose its potential new functions. As a result of investigation, (1) regioselective direct arylation of the carbon-hydrogen bond of azulene, (2) method for incorporation of azulene rings into phenacene and acene skeletons, and (3) regioselective arene homologation through deoxygenative aromatization were developed, and the performance of the resulting products as components for organic field-effect transistors was evaluated.

Free Research Field

有機合成化学

Academic Significance and Societal Importance of the Research Achievements

本研究で得られた縮環芳香族炭化水素は、アズレン骨格に由来した狭いHOMO-LUMOギャップを有し、凝集状態において、双極子に沿ってその会合構造を制御可能な新規分子デバイス素子として期待できる。本研究で確立したアズレンの効率的な官能基化法を駆使することで、様々な新しい類縁体の物性を明らかにでき、電子材料を設計する上での新たな指針を得ることができた。