A Stable Triplet-Ground-State Conjugated Diradical Based on a Diindenopyrazine Skeleton.

High-spin conjugated radicals have great potential in magnetic materials and organic spintronics. However, to obtain high-spin conjugated radicals is still quite challenging due to their poor stability. We report the successful synthesis and isolation of a stable triplet conjugated diradical, 10,12-diaryldiindeno[1,2-b:2',1'-e]pyrazine (m-DIP). With the m-xylylene analogue skeleton containing electron-deficient sp2 -nitrogen atoms, m-DIP displays significant aromatic character within its pyrazine ring and its spin density mainly delocalizes on the meta-pyrazine unit, making it a triplet ground state conjugated diradical. Our work provides an effective "spin density tuning" strategy for stable high-spin conjugated radicals.