Functionalizations of Nitrogen-doped Polycyclic Aromatic Compounds

2019 Fiscal Year Final Research Report

• Project/Area Number: 18K14199
• Research Category: Grant-in-Aid for Early-Career Scientists
• Allocation Type: Multi-year Fund
• Review Section: Basic Section 33010:Structural organic chemistry and physical organic chemistry-related
• Research Institution: Kyoto University
• Principal Investigator: Tanaka Takayuki 京都大学, 理学研究科, 助教 (20705446)
• Project Period (FY): 2018-04-01 – 2020-03-31
• Keywords: サーキュレン / 求核置換反応 / 蛍光 / 非平面構造 / 溶解性 / ラジカルカチオン / コロール / 反芳香族性

Outline of Final Research Achievements

I have explored novel polycyclic aromatic hydrocarbons containing nitrogen atoms in the core. Particular focus has been provided to their distorted structures induced by peripheral functionalization, and molecular assembly. For this purpose, I developed new reactions such as nucleophilic aromatic substitution reaction to form diazadithia[8]circulene and palladium-catalyzed amination reaction on corannulene. The structures of new products were revealed by X-ray diffraction analysis. Studies on their solubility in organic solvents and photophysical properties have been also conducted.

Free Research Field

有機化学

Academic Significance and Societal Importance of the Research Achievements

湾曲した構造をもつ分子の合成は一般に難しく、自らが開発したオリジナル分子を非平面構造に展開した意義は大きい。さらに、そうした非平面構造の含窒素多環芳香族炭化水素化合物に特有の物性の解明にも挑み、ラジカルカチオンの安定化や溶解性の高さなど、有機電子材料や有機磁性材料として有用な性質を見出した。