Creation of new neutral substituents exhibiting strong pi-electron donating ability and their application to the development of novel organic fluorescent dyes

2022 Fiscal Year Final Research Report

• Project/Area Number: 21K15222
• Research Category: Grant-in-Aid for Early-Career Scientists
• Allocation Type: Multi-year Fund
• Review Section: Basic Section 47010:Pharmaceutical chemistry and drug development sciences-related
• Research Institution: Kanazawa University
• Principal Investigator: Hikaru Fujita 金沢大学, 薬学系, 助教 (40782850)
• Project Period (FY): 2021-04-01 – 2023-03-31
• Keywords: 電子供与基 / π電子密度制御 / 蛍光色素

Outline of Final Research Achievements

The enhancement of π-electron density in conjugated systems based on the resonance effect of π-electron-donating groups plays an important role in controlling the physical properties, chemical reactivity, and optical properties of π-system molecules. In push-pull fluorescent dyes, which are commonly used for fluorescence imaging, π-electron-donating groups are often introduced to enhance absorption and fluorescence and to extend their wavelength. However, the π-electron-donating ability of the conventional substituents is limited, and this has been a limiting factor in the development of π-based functional molecules such as organic fluorescent dyes. In this research project, we succeeded in creating a new ylidic nitrogen substituent that is electrically neutral and exhibits higher π-electron-donating ability than the conventional substituents, and in developing new organic fluorescent dyes using this substituent to confirm its usefulness.

Free Research Field

有機化学

Academic Significance and Societal Importance of the Research Achievements

本研究で開発されたイリド型窒素置換基は学術新規性が高く、これを含む有機蛍光色素の合成及びその光学特性の解明は本研究で初めて達成されたものである。本置換基のイリド部位は構造的多様性に富むため、分子設計上の応用性にも優れている。本研究で利用した蛍光色素骨格は代表的なものにとどまっているものの、今後、このイリド型窒素置換基を導入した様々な新規蛍光色素の開発が進展すれば、生命科学研究に有用な分子ツールが多数見出されると期待される。