Tridecacyclene Tetraimide: An Easily Reduced Cyclooctatetraene Derivative

Tridecacyclene tetraimide, TCTI, an electron-deficient non-benzenoid nanocarbon with a C56N4 polycyclic framework was obtained in a concise synthesis. TCTI has a non-planar structure and forms pi-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.

Automated summary

Tridecacyclene tetraimide (TCTI), an electron-deficient non-benzenoid nanocarbon, was synthesized with a concise method. TCTI has a non-planar structure and forms pi-stacked dimers in the solid state. In solution, it undergoes eight single-electron reductions, resulting in a range of negatively charged states. The TCTI anions exhibit extended near-infrared absorptions, with a strong band at 1692 nm for the dianion. Computational analysis indicates that the stability of TCTI anions is attributed to the electron-deficient imide groups and the local aromaticity of the reduced acenaphthylene units. TCTI shows potential applications in electrochromic and charge storage fields.