Solution-phase synthesis of Clar's goblet and elucidation of its spin properties.

In the traditional view, spin pairing occurs between two electrons in a chemical bond where the bonding interaction compensates for the penalty of electrostatic repulsion. It is a mystery whether spin pairing can occur between two non-bonded electrons within a molecular entity. Unveiling this type of spin entanglement (that is, pairing between two spatially segregated spins) at the molecular scale is a long-standing challenge. Clar's goblet, proposed by Erich Clar in 1972, provides an ideal platform to verify this unusual property. Here we report the solution-phase synthesis of Clar's goblet and experimental elucidation of its spin properties. Magnetic studies reveal that the two spins are spatially segregated with an average distance of 8.7 Å and antiferromagnetically coupled in the ground state with an ΔE of -0.29 kcal mol. Our results provide insight into the spin entanglement in Clar's goblet and may inspire the design of correlated molecular spins for quantum information technologies.