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Carborane-arene fused boracyclic analogues of polycyclic aromatic hydrocarbons accessed by intramolecular borylation. | LitMetric

AI Article Synopsis

  • Arenes are flat 2D aromatic compounds, while dicarbadodecaborane clusters are considered 3D aromatic molecules.
  • This research focuses on creating new compounds that combine both 2D and 3D aromatic features, specifically boron-doped versions of polycyclic aromatic hydrocarbons.
  • The study shows that the -carborane group helps facilitate the bonding of boron to the arene, leading to the formation of boracycles, with computational modeling suggesting a simultaneous reaction approach and high efficiency in light-absorbing capabilities for the six-membered structures.

Article Abstract

Arenes are 2D aromatics while dicarbadodecaborane clusters are branded as 3D aromatic molecules. In this work we prepare molecules that feature fused 2D/3D aromatic systems that represent boron-doped analogues of polycyclic aromatic hydrocarbons. The electron withdrawing nature of the -carborane substituent enables swift arene borylation on boron bromide or hydride precursors to furnish five- and six-membered boracycles in conjugation with the arene. The mechanism was modeled by DFT computations implying a concerted transition state and analyzing the photophysical properties revealed high quantum yields in the six-membered systems.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC11110167PMC
http://dx.doi.org/10.1039/d4sc00990hDOI Listing

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