Enhancing Dual-State Emission in Maleimide Fluorophores through Fluorocarbon Functionalisation

Maria Pervez, Amanda K. Pearce, Jonathan T. Husband, Louise Male, Miquel Torrent-Sucarrat, Rachel K. O'Reilly

Research output: Contribution to journalArticlepeer-review

1 Citation (SciVal)


Herein, a library of trifluoroethyl substituted aminomaleimide derivatives are reported with small size and enhanced emissions in both solution and solid-state. A diCH2CF3 substituted aminochloromaleimide exhibits the most efficient dual-state emission (Φf >50 % in solution and solid-state), with reduced quenching from protic solvents. This is attributed to the reduction of electron density on the maleimide ring and suppressed π-π stacking in the solid-state. This mechanism was explored in-depth by crystallographic analysis, and modelling of the electronic distribution of HOMO-LUMO isosurfaces and NCI plots. Hence, these dual-state dyes overcome the limitations of single-state luminescence and will serve as an important step forward for this rapidly developing nascent field.

Original languageEnglish
Article numbere202201877
JournalChemistry - A European Journal
Issue number58
Early online date20 Jul 2022
Publication statusPublished - 18 Oct 2022


  • aminochloromaleimide
  • dual-state emission
  • fluorocarbons
  • maleimide fluorophores
  • monoaminomaleimide

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry


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