Development of nitrogen-based redox system with multi-functionalities

2021 Fiscal Year Final Research Report

• Project/Area Number: 19K15536
• 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: Shizuoka University
• Principal Investigator: Fujimoto Keisuke 静岡大学, 工学部, 助教 (10824542)
• Project Period (FY): 2019-04-01 – 2022-03-31
• Keywords: 多環芳香族化合物 / 機能性色素 / 酸化還元活性 / 発光材料 / 有機半導体 / 近赤外吸収 / ビタミンB2

Outline of Final Research Achievements

We succeeded in developing a series of polycyclic heteroaromatic compounds (PHAs) which possesses nitrogen-based redox functionality. As a redox-active substructure, 1,4-diazabutadiene linkage was employed, mimicking the functionality of natural coenzyme of flavin adenine dinucleotide. As a unique reactivity, the compounds underwent reversible redox interconversion between amine-type structure and imine-type structure with dramatically switching their electronic and chromophoric properties. Moreover, we investigated the structure-property relationship of the redox active PHAs by changing π-electronic network or attaching the electron-withdrawing substituent.

Free Research Field

有機化学

Academic Significance and Societal Importance of the Research Achievements

本研究では、新しいコンセプトに従ったπ電子系化合物の開発と物性評価を達成しており、有機材料の構造-物性相関に関する知見を深めるうえで学術的意義がある。また、本研究で得られた化合物は窒素原子中心の酸化還元に基づいた独自の反応性を示すため、独自の有機機能性材料開発につながることが期待される。例えば、有機n型半導体、環境応答性発光材料および酸化触媒としての応用展開が予測される。