Synthesis and fluorescent properties of quinoxaline derived ionic liquids

Ionic liquids (ILs) have attracted increasing attention since last few decades due to their high molecular design abilities and wide applications in different fields. In this study, four novel fluorescent isoquinolino [2,1-a]quinoxalin-5-ium ILs were designed and synthesized via a two-step process including a simple dual Schiff's base formation and a subsequent [RhCp*Cl-2](2)-catalyzed oxidative C-H activation/annulation reaction. The as-synthesized ILs were extensively characterized using FT-IR, H-1-NMR, C-13-NMR, F-19-NMR, HSQC-NMR, HMBC-NMR and HR-MS. Their photophysical properties were determined by steady-state fluorescence spectroscopy. The results demonstrate that all these ILs showed dual or triple emissions, large stokes shift (90 nm) and mechanochromic behaviors. Basing on solvatochromism and titration experiments, it is thought that the emission bands of the ILs are raised from their local excited states, charge transfer states or excited state proton transfer of cations, while the substitute effect of these quinoxaline derived ILs on their stokes shifts is negligible. (C) 2021 Institute of Process Engineering, Chinese Academy of Sciences. Publishing services by Elsevier B.V. on behalf of KeAi Communi-cations Co., Ltd.

Automated summary

This study presents the design and synthesis of four novel fluorescent ionic liquids through a simple reaction process. The synthesized ionic liquids were extensively characterized and their photophysical properties were determined. The results reveal that these ionic liquids exhibit dual or triple emissions, large stokes shift, and mechanochromic behaviors.