In summary, we realized the solution-phase synthesis and isolation of the Clar's goblet derivative cg-2 with bulky substituents. The precise construction of its topologically frustrated sp 2 -C network was achieved through an intermolecular radical-radical coupling approach. The synthetic scalability and kinetical inertness of cg-2 allow us to experimentally elucidate the long-standing doubt about the interaction between the two spins in Clar's goblet. Magnetic studies reveal that the two spins are spatially segregated in Clar's goblet with an average distance of 8.7 Å, and are AFM coupled in the ground state. The singlet ground state can be thermally excited to a triplet state with an ∆ES-T of -0.29 kcal/mol. Furthermore, the spatial segregation of spin/charge can be directly observed through EPR splitting in the radical cation state of cg-2. This spin pairing discovered in Clar's goblet not only suggests a spin entanglement phenomenon at the molecular scale, but also may enable practical logic operations in spin-based quantum computation. Finally, we hope this study could inspire and motivate further efforts to uncover the fundamental mechanism of this spin entanglement and push the application of tailor-made molecular spins in quantum information technologies.