Chemistry of sumanene.

Sumanene (C21 H12 ) is a bowl-shaped π-conjugated molecule with C3v symmetry, consisting of alternating benzene rings and cyclopentadiene rings around the central benzene ring. The structure corresponds to the smallest C3v-symmetric fragment for the structural motifs of fullerenes or end-caps of carbon nanotubes. The presence of three sp(3)-hybridized benzylic sites is one of the most characteristic structural features in sumanene, which allows the different chemistry from that of corannulene. Since our first synthesis in 2003, we have engaged in the study of sumanene. This article summarizes our continuous study, including the synthesis, structure, dynamics, derivatization, complexation with transition metals, charge carrier mobility, and conversion to nitrogen-doped graphitic carbon, of sumanene.