Air-Stable Thin Films with High and Anisotropic Electrical Conductivities Composed of a Carbon-Centered Neutral π-Radical

[Image: see text] Air-stable thin films (50–720 nm thickness) composed of a carbon-centered neutral π-radical with high and anisotropic electrical conductivities were fabricated by vapor deposition of 4,8,12-trioxotriangulene (TOT). The thin films were air-stable over 15 months and were the aggregate of TOT microcrystals, in which a one-dimensional π-stacking column was formed through the strong singly occupied molecular orbital (SOMO)–SOMO interaction with two-electron-multicenter bond among the spin-delocalized π-planes. The orientations of the one-dimensional column of TOT were changed depending on the deposition rate and substrates, where face-on-oriented thin films were epitaxially grown on the graphite 0001 surface, and edge-on-oriented thin films were grown on glass, SiO(2), and indium tin oxide substrates under a high-deposition rate condition. The films showed high electrical conductivities of 2.5 × 10(–2) and 5.9 × 10(–5) S cm(–1) along and perpendicular to the π-stacking column, respectively, for an edge-on oriented thin film.