Pentagon-Embedded Cycloarylenes with Cylindrical Shapes

Shunpei Hitosugi, Sota Sato, Taisuke Matsuno, Takashi Koretsune, Ryotaro Arita, Hiroyuki Isobe

Research output: Contribution to journalArticlepeer-review

35 Citations (Scopus)


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.

Original languageEnglish
Pages (from-to)9106-9110
Number of pages5
JournalAngewandte Chemie - International Edition
Issue number31
Publication statusPublished - 2017 Jul 24


  • conjugation
  • macrocycles
  • nanostructures
  • nanotubes
  • pentagons


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