Carborane-induced excimer emission of severely twisted bis-o-carboranyl chrysene

Adam V. Marsh, Nathan J. Cheetham, Mark Little, Matthew Dyson, Andrew J.P. White, Peter Beavis, Colin N. Warriner, Anthony C. Swain, Paul N. Stavrinou, Martin Heeney

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Abstract

The synthesis of a highly twisted chrysene derivative incorporating two electron deficient o-carboranyl groups is reported. The molecule exhibits a complex, excitation-dependent photoluminescence, including aggregation-induced emission (AIE) with good quantum efficiency and an exceptionally long singlet excited state lifetime. Through a combination of detailed optical studies and theoretical calculations, the excited state species are identified, including an unusual excimer induced by the presence of o-carborane. This is the first time that o-carborane has been shown to induce excimer formation ab initio, as well as the first observation of excimer emission by a chrysene-based small molecule in solution. Bis-o-carboranyl chrysene is thus an initial member of a new family of o-carboranyl phenacenes exhibiting a novel architecture for highly-efficient multi-luminescent fluorophores.

Original languageEnglish
Pages (from-to)10640-10645
Number of pages6
JournalAngewandte Chemie - International Edition
Volume57
Issue number33
DOIs
Publication statusPublished - 13 Aug 2018

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Keywords

  • Aggregation-induced emission
  • Carboranes
  • Chrysene
  • Excimers
  • Intramolecular charge transfer
  • intramolecular charge transfer
  • chrysene
  • carboranes
  • aggregation-induced emission
  • excimers

Cite this

Marsh, A. V., Cheetham, N. J., Little, M., Dyson, M., White, A. J. P., Beavis, P., ... Heeney, M. (2018). Carborane-induced excimer emission of severely twisted bis-o-carboranyl chrysene. Angewandte Chemie - International Edition, 57(33), 10640-10645. https://doi.org/10.1002/anie.201805967