A novel amphiphilic TTF hexamer 1 with a flexible disk-like structure and strong self-aggregation properties has been synthesized. Nanowires fabricated from both 1 and its cation radical 1(center dot+) in CHCl3/hexane solutions have a hexagonal columnar structure. In contrast, drop-cast films of 1 and 1(center dot+) exhibit an edge-to-edge close-packed arrangement stacking vertical to the drop-cast surface, indicating stronger dictating effect of surface area for the nanostructure fabrication. The electric conductivity of the wire of1(center dot+) is 2 orders of magnitude higher than that of the film of 1(center dot+), reflecting the nanostructured, one-dimensional morphology.