Synthesis of a hydrogenated zigzag carbon nanobelt

Abstract

Zigzag carbon nanobelts are a long-sought-after yet unrealized target for organic synthesis. Herein, we report a study toward the synthesis of tetrabenzo [10]cyclacene, an undocumented zigzag carbon nanobelt. The synthetic precursor of tetrabenzo [10]cyclacene is its box-shaped tetraepoxy derivative, which is synthesized through iterative Diels–Alder reactions utilizing a “C”-shaped building block. Attempted aromatization of this tetraepoxy nanobox toward the formation of a fully conjugated nanobelt results in an octahydro derivative of tetrabenzo[10]cyclacene. The structures of the tetraepoxy nanobox and octahydrotetrabenzo[10]cyclacene were both unambiguously identified with single-crystal X-ray crystallography.