Borazatruxenes Synthesized

  • Author:
  • Published: 02 September 2019
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
  • Source / Publisher: Chemical Science/Royal Society of Chemistry
  • Associated Societies: Royal Society of Chemistry (RSC), UK
thumbnail image: Borazatruxenes Synthesized

Polycyclic aromatic hydrocarbons (PAHs) can be useful, e.g., in organic electronic components. One compound of this type is truxene, a heptacyclic structure with threefold rotational symmetry. Truxenes have a central benzene core.

Dan Pantoş and colleagues, University of Bath, UK, have synthesized a series of substituted arene-borazine hybrids called borazatruxenes (pictured). In these compounds, the central benzene ring of truxene is replaced with a borazine ring (B3N3). This changes the electronic structure of the compounds significantly, while the structure remains very similar to the parent truxene.

The team started their synthesis from meta- and para-substituted 2-formylbenzeneboronic acids or 2-cyanobenzeneboronic esters, which were subjected to a ring-closing reaction to give amine-borane products (BN analogs of indane). Three equivalents of these bicyclic systems were combined under microwave irradiation to form the central borazine ring and give the desired products.

Usually, borazine-modified PAHs are moisture-sensitive, but the borazatruxenes are air- and moisture-stable. According to the researchers, the compounds could be useful in molecular electronic devices.



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