Tridecacyclene Tetraimide: An Easily Reduced Cyclooctatetraene Derivative

Tridecacyclene tetraimide, TCTI, an electron‐deficient non‐benzenoid nanocarbon with a C(56)N(4) polycyclic framework was obtained in a concise synthesis. TCTI has a non‐planar structure and forms π‐stacked dimers in the solid state. In solution, it undergoes eight single‐electron reductions, yielding a range of negatively charged states up to an octaanion. Except for the latter species, which has a remarkably large electronic gap, the anions feature extended near‐infrared absorptions, with a particularly strong band at 1692 nm observed for the dianion. A computational analysis of the TCTI anions shows that their stability originates from the combined effects of electron‐deficient imide groups and the local aromaticity of reduced acenaphthylene units. The properties of TCTI make it potentially useful in electrochromic and charge storage applications.