Synthesis and functionalization of Y-shaped polycyclic aromatic hydrocarbon

2023 Fiscal Year Final Research Report

• Project/Area Number: 20K15262
• 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: Fukuoka University
• Principal Investigator: MIYAZAKI Takaaki 福岡大学, 理学部, 助教 (70788504)
• Project Period (FY): 2020-04-01 – 2024-03-31
• Keywords: 多環芳香族炭化水素 / 蛍光ソルバトクロミズム / 構造有機化学

Outline of Final Research Achievements

As Y-shaped polycyclic aromatic hydrocarbons, 2,3-naphthalimide fused with two benzothiophene or benzofuran rings (1 and 2, respectively) were designed to realize new functional compounds. 1 and 2 have a push-pull structure due to the imide group and benzothiophene or benzofuran rings. 1 and 2 were successfully synthesized in three steps. The absorption and fluorescence spectra were measured in several different solvents to reveal the electronic structures and optical properties of 1 and 2. As a result, 1 and 2 showed fluorosoluvatochromic behaviors: different fluorescent colors are observed depending on solvents. For instance, the fluorescent color of 1 was blue in cyclohexane and yellow in methanol. In addition, the fluorosolvatochromic behaviors were estimated by ET(30) and Lippert-Mataga plots, indicating that solvent polarity is an important factor in fluorosolvatochromism.

Free Research Field

構造有機化学

Academic Significance and Societal Importance of the Research Achievements

本研究によって、push-pull型のY字型多環芳香族炭化水素は容易に合成可能であり、さらにそのように合成された化合物が蛍光ソルバトクロミズム特性を示すことを明らかとすることができた。これは多環芳香族炭化水素に機能性を付与するにあたり、ひとつの分子設計の指針となることが期待できる。また、今回見出された蛍光ソルバトクロミズム特性は蛍光イメージング等に応用可能なものであることから、本成果を基盤とすることでさらなる優れた有機機能性材料の開発に貢献するものと期待できる。