Synthesis of shape-persistent carbon nanorings or carbon-based macrocycles containing extended conjugated -electron systems has fascinated chemists due to their unique molecular geometry and the associated characteristic properties. The increasing importance of carbon-rich compound as materials has caused this area grow and expand into an interdisciplinary area. Among the synthetic studies of such compounds, the synthesis of p-phenylene compounds with various geometries has attracted attention, as represented by the chemistry of cycloparaphenylene molecules. Recent examples of such compounds with a unique geometry include molecules with motifs including spoked wheels, cages, tri-helicates, lemniscates, Möbius loops, catenane and trefoil knots. We also reported on a p-phenylene molecule with an S-shaped geometry, as demonstrated by the synthesis of the linear [3]spirobifluorenylene 1 consisting of the three spirobifluorene units, where the stereochemistry of 1 is RPR/SMS (Figure ). In the present study, we focused on the structural motif of the woven pattern found in textiles. Figure shows typical examples of triaxial and diaxial weave patterns. The designed chiral carbon nanorings 2- [n] are constructed by the cyclic connection of spirobifluorene with the same chirality, i.e., RRR or SSS (Figure ). The structures also can be viewed as macrocycles with helically arranged p-quaterphenyl rods. The carbon nanorings 2-[3] and 2- [4] have the same geometric arrangements as units of triaxial and diaxial weave patterns, respectively, in which the spirobifluorene corresponds to the crossing in these weaves. The pentagonal molecule 2- [5] represents a geometrical partial unit with a more elaborate weave involving five sets of threads. Although many unique pphenylene molecules have been synthesized to date, those based on a weave-motif has not yet been studied, to the best of our knowledge. Moreover, these types of molecules 2- [n] are expected to possess a unique type of spiroconjugation as well as characteristic chiroptical properties. More specifically, multiple orbital interactions in this system will lead to an electronic configuration that is distinct from that of a simple spirobifluorene (Figure ). Such homoconjugation based on multiple -conjugated units arranged cyclically via spirocarbons has not been investigated. In addition, a three-dimensional π-conjugation based on spiroconjugation is expected to contribute to the development of charge carrier transport materials. Here, we report on the synthesis, structure, spectroscopic properties and spiroconjugation of chiral cyclic [n]