The key feature of instability of small non-IPR closed-shell fullerenes: three isomers of C40

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Pentagon-Embedded Cycloarylenes with Cylindrical Shapes

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.     

Strain Release of Fused Pentagons in Fullerene Cages by Chemical Functionalization

According to the isolated pentagon rule (IPR), for stable fullerenes, the 12 pentagons should be isolated from one another by hexagons, otherwise the fused pentagons will result in an increase in the local steric strain of the fullerene cage. However, the successful isolation of more than 100 endohedral and exohedral fullerenes containing fused pentagons over the past 20 years has shown that strain release of fused pentagons in fullerene cages is feasible. Herein, we present a general overview on fused‐pentagon‐containing (i.e. non‐IPR) fullerenes through an exhaustive review of all the types of fused‐pentagon‐containing fullerenes reported to date. We clarify how the strain of fused pentagons can be released in different manners, and provide an in‐depth understanding of the role of fused pentagons in the stability, electronic properties, and chemical reactivity of fullerene cages.