Stereoisomerism, crystal structures, and dynamics of belt-shaped cyclonaphthylenes

Zhe Sun, Takuya Suenaga, Parantap Sarkar, Sota Sato, Motoko Kotani, Hiroyuki Isobe

Research output: Contribution to journalArticlepeer-review

38 Citations (Scopus)

Abstract

The chemistry of a belt-shaped cyclic array of aromatic panels, a socalled "nanohoop," has increasingly attracted much interest, partly because it serves as a segmental model of single-wall carbon nanotubes with curved sp2-carbon networks. Although the unique molecular structure of nanohoops is expected to deepen our understanding in curved π-systems, its structural chemistry is still in its infancy despite structural variants rapidly accumulated over the past several years. For instance, structural characteristics that endow the belt shapes with rigidity, an important structural feature relevant to carbon nanotubes, have not been clarified to date. We herein report the synthesis and structures of a series of belt-shaped cyclonaphthylenes. Random synthesis methods using three precursor units with different numbers of naphthylene panels allowed us to prepare 6 congeners consisting of 6 to 11 naphthylene panels, and relationships between the rigidity and the panel numbers, i.e., molecular structures, were investigated. Fundamental yet complicated stereoisomerism in the belt-shaped structures was disclosed by mathematical methods, and dynamics in the panel rotation was revealed by dynamic NMR studies with the aid of theoretical calculations.

Original languageEnglish
Pages (from-to)8109-8114
Number of pages6
JournalProceedings of the National Academy of Sciences of the United States of America
Volume113
Issue number29
DOIs
Publication statusPublished - 2016 Jul 19

Keywords

  • Carbon nanotubes
  • Crystal structures
  • Dynamic structures
  • Macrocycles
  • Stereoisomerism

ASJC Scopus subject areas

  • General

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