Highly Deformed o-Carborane Functionalised Non-linear Polycyclic Aromatics with Exceptionally Long C−C Bonds

Adam V. Marsh, Mark Little, Nathan J. Cheetham, Matthew J. Dyson, Matthew Bidwell, Andrew J.P. White, Colin N. Warriner, Anthony C. Swain, Iain McCulloch, Paul N. Stavrinou (Corresponding author), Martin Heeney (Corresponding author)

Research output: Contribution to journalArticleAcademicpeer-review

Abstract

The effect of substituting o-carborane into the most sterically hindered positions of phenanthrene and benzo(k)tetraphene is reported. Synthesised via a Bull–Hutchings–Quayle benzannulation, the crystal structures of these non-linear acenes exhibited the highest aromatic deformation parameters observed for any reported carborane compound to date, and among the largest carboranyl C−C bond length of all organo-substituted o-carboranes. Photoluminescence studies of these compounds demonstrated efficient intramolecular charge-transfer, leading to aggregation induced emission properties. Additionally, an unusual low-energy excimer was observed for the phenanthryl compound. These are two new members of the family of carborane-functionalised non-linear acenes, notable for their peculiar structures and multi-luminescent properties.

Original languageEnglish
Pages (from-to)1970-1975
Number of pages6
JournalChemistry - A European Journal
Volume27
Issue number6
DOIs
Publication statusPublished - 26 Jan 2021

Keywords

  • AIE
  • carboranes
  • charge transfer
  • fluorescence
  • polycyclic aromatic hydrocarbons

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