Juggling Optoelectronics and Catalysis: The Dual Talents of Bench Stable 1,4‐Azaborinines

• Published in: Chemistry : a European journal Vol. 30; no. 8; pp. e202301944 - n/a
• Main Authors: Beek, Chloe M., Swarbrook, Amelia M., Creissen, Charles E., Hawes, Chris S., Gazis, Theodore A., Matthews, Peter D.
• Format: Journal Article
• Language: English
• Published: Germany Wiley Subscription Services, Inc 07-02-2024; John Wiley and Sons Inc
• Subjects: Anthracene; azaborinine; Boron; boron heterocycles; Carbonyl compounds; Carbonyls; Catalysis; Catalysts; hydroboration; Imines; Nitrogen; optoelectronic properties; Optoelectronics; Polycyclic aromatic hydrocarbons; catalysis; optoelectronic properties; hydroboration; polycyclic aromatic hydrocarbons; azaborinine; boron heterocycles
• ISSN: 0947-6539; 1521-3765; 1521-3765
• DOI: 10.1002/chem.202301944

Boron‐ and nitrogen‐doped polycyclic aromatic hydrocarbons (B‐PAHs) have established a strong foothold in the realm of organic electronics. However, their catalytic potential remains largely untapped. In this study, we synthesise and characterise two bench stable B,N‐doped PAH derivatives based on a 1,4‐azaborinine motif. Most importantly, the anthracene derived structure is an efficient catalyst in the reduction of various carbonyls and imines. These results underscore the potential of B,N‐PAHs in catalytic transformations, setting the stage for deeper exploration in this chemical space.
Bench stable 1,4‐azaborinine PAHs with an anthracene or ladder‐type pentacene scaffold have been prepared, characterised and proven to be efficient catalysts for hydroboration of carbonyls and imines.