Enhancing dual-state emission in maleimide fluorophores through fluorocarbon functionalisation

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

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

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Abstract

Herein, a library of trifluoroethyl substituted aminomaleimide derivatives are reported with small size and enhanced emissions in both solution and solid-state. A di-CH 2 CF 3 substituted aminochloromaleimide exhibits the most efficient dual state emission ( Φ f > 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
Number of pages7
JournalChemistry: A European Journal
Volume28
Issue number58
Early online date20 Jul 2022
DOIs
Publication statusE-pub ahead of print - 20 Jul 2022

Bibliographical note

Publisher Copyright:
© 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.

Keywords

  • Research Article
  • Research Articles
  • aminochloromaleimide
  • dual-state emission
  • fluorocarbons
  • maleimide fluorophores
  • monoaminomaleimide

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