Tridecacyclene Tetraimide: An Easily Reduced Cyclooctatetraene Derivative

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