Self-assembly of semiconducting polymers has been widely investigated due to intriguing optoelectronic properties for the application. Among the various multidimensional nanostructures, 2D materials have received the most attention due to their intriguing electronic performances but introducing an anisotropic orientation remains challenging. Here, we demonstrate a new direct formation of various large-area 2D nanosheets resembling leaves, rectangles, and rafts by the living cyclopolymerization of a 1,6-heptadiyne monomer containing a fluorene moiety. Based on high-resolution transmission electron microscopy and X-ray diffraction analysis, we suggest that orthorhombic crystalline packing of the resulting conjugated polymer is the basis of 2D sheet formation. Furthermore, this unique interdigitating slip-stack packing model enables the synthesis of super-rigid 1D nanoribbon through a block copolymer. The fluorescence of both structures enable the super-resolution fluorescent imaging, thereby allowing for the real-time monitoring of the individual nanostructures in solution.