Quinoidal Azaacenes: 99 % Diradical Character

Angew Chem Int Ed Engl. 2020 Jul 20;59(30):12396-12401. doi: 10.1002/anie.201915977. Epub 2020 Apr 28.

Abstract

Quinoidal azaacenes with almost pure diradical character (y=0.95 to y=0.99) were synthesized. All compounds exhibit paramagnetic behavior investigated by EPR and NMR spectroscopy, and SQUID measurements, revealing thermally populated triplet states with an extremely low-energy gap ΔEST' of 0.58 to 1.0 kcal mol-1 . The species are persistent in solution (half-life≈14-21 h) and in the solid state they are stable for weeks.

Keywords: acenes; heteroaromatics; radicals; structure elucidation; synthetic methods.