Synthesis and Fluorescence Properties of Pyrimidine Based Bisboron Complexes Having D–π–A Structure

Yasuhiro Kubota,  Kazumasa Funabiki,  Masaki Matsui
Gifu University


Abstract

Organoboron complexes are one of the most important fluorescent dyes and have been applied to various fields including optoelectronics and biomedical applications. Since the fluorescent properties are strongly depended on the type of the ligand, the development of novel or improved boron complexes have been actively carried out. Recently, near-infrared (NIR) emitting organic compounds have become the focus of attention due to potential applications in NIR light-emitting diodes, telecommunications, and bio-imaging. Some boron complexes exhibiting NIR fluorescence in solution including BODIPY dye have been reported so far. However, due to aggregation-cased quenching (ACQ), little has been reported on organoboron complexes showing fluorescence beyond 700 nm in the solid state. To the best of our knowledge, only one type of boron complex, which is the boron complex of 2’-hydoroxychalcone, has been reported as such complex. In this light, binuclear boron complexation is an effective strategy for bathochromic shift of absorption and fluorescence wavelength. There have been some reports about bisboron complexes showing NIR fluorescence in solution. Additionally, donor–π–acceptor structure leads to intramolecular charge transfer (ICT), consequently causes a bathochromic spectral shift. Previously, we have reported that boron complexes having β-iminoenolate ligand can be easily synthesized and showed interesting fluorescence properties such as solid-state fluorescence, aggregation-induced emission enhancement (AIEE), solvatochromic fluorescence, and dual fluorescence. In this conference, we will report the synthesis and fluorescence properties of pyrimidine based bisboron complexes with β-iminoenolate ligands having D–π–A structure which show solid-state fluorescence in long wavelength region.