Pentagon‐Embedded Cycloarylenes with Cylindrical Shapes

Abstract Cylinder‐shaped graphitic networks in carbon nanotubes have attracted interest from scientists in various disciplines. The chemical synthesis of segments thereof is considered as a challenging and appealing subject in chemistry, and deepens our understanding of curved and conjugated arrays of hexagons. We herein report the synthesis of cylinder‐shaped molecules containing non‐hexagon bridges in their conjugated systems. Multiple pentagon units were embedded in the cylinder‐shaped discrete molecules, and the stereoisomerism originating from their helical carbon arrangements was studied. Structural analysis by NMR, UV/Vis absorption spectroscopy, and single‐crystal X‐ray diffraction provided fundamental experimental information on the curved systems with conjugation across the pentagons. This study provides the first experimental guide for further explorations of anomalous non‐hexagon arrays of graphitic carbon materials with cylindrical shapes.