Issue 20, 2024

Carborane–arene fused boracyclic analogues of polycyclic aromatic hydrocarbons accessed by intramolecular borylation

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 ortho-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.

Graphical abstract: Carborane–arene fused boracyclic analogues of polycyclic aromatic hydrocarbons accessed by intramolecular borylation

Supplementary files

Article information

Article type
Edge Article
Submitted
10 feb 2024
Accepted
13 apr 2024
First published
16 apr 2024
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2024,15, 7568-7575

Carborane–arene fused boracyclic analogues of polycyclic aromatic hydrocarbons accessed by intramolecular borylation

Y. Li, M. Tamizmani, M. O. Akram and C. D. Martin, Chem. Sci., 2024, 15, 7568 DOI: 10.1039/D4SC00990H

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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