Development of the novel organic fluorophore-based on the non-pi-conjugated small skeleton

2023 Fiscal Year Final Research Report

• Project/Area Number: 21K05025
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Review Section: Basic Section 33010:Structural organic chemistry and physical organic chemistry-related
• Research Institution: Keio University
• Principal Investigator: Miura Youhei 慶應義塾大学, 理工学部(矢上), 講師 (30708532)
• Project Period (FY): 2021-04-01 – 2024-03-31
• Keywords: 有機蛍光体 / イミダゾール / 有機結晶

Outline of Final Research Achievements

The aim of this study was to develop a non-π-extended small molecule with stimuli-responsive fluorescent properties by using imidazole, a small, neutral, and minimal aromatic ring, as the main framework. Compounds of the imidazole derivative with arylethynyl and benzoyl groups and organoboron complexes derived from them were newly developed and their fluorescent properties were investigated. Both compounds exhibited repeatable mechanofluorochromism. The boron complexes showed versatile fluorescence properties such as large Stokes shift above 100 nm in the solution and thermofluorochromism. These results indicate that a new fluorescent molecular system based on imidazole has been successfully developed.

Free Research Field

構造有機化学

Academic Significance and Societal Importance of the Research Achievements

多くの有機蛍光分子ではπ拡張を行うことで蛍光特性の制御を行うことがほとんどであった。本研究では小分子骨格としてイミダゾールを主骨格とした蛍光分子を開発に成功し、新しい蛍光分子の設計指針を示す事が出来た。
また、新規有機ホウ素錯体は固体、溶液で高い蛍光特性を示すとともに、熱や摩砕などに応答する刺激応答性を示した。この有機ホウ素錯体はBODIPYと同等の新しい蛍光分子骨格として、センサーやプローブ等様々な材料への応用が期待される。