Triplet ground state derivative of aza-m-xylylene diradical with large singlet-triplet energy gap.

Organic molecules with a strong preference for triplet ground states, in which the triplet state is below the lowest singlet state by ≥10 kcal/mol, are typically short-lived and mostly detected as reactive intermediates. We now report a triplet ground state derivative of aza-m-xylylene diradical with a large singlet-triplet energy gap (ΔE(ST)) of ∼10 kcal/mol, which is comparable to ΔE(ST) for the well-known reactive intermediate m-xylylene diradical. The aminyl diradical persists in solution at room temperature on the time scale of minutes.