An Obtuse-angled Corner Unit for Fluctuating Carbon Nanohoops

Zhe Sun, Naoya Miyamoto, Sota Sato, Hidetoshi Tokuyama, Hiroyuki Isobe

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)

Abstract

The invention of corner units was the key factor that allowed the synthesis of cyclo-para-phenylenes with strained curved π-systems. Despite only a few scarce instances of the development of corner units to date, a variety of structural congeners have been synthesized. These preceding corner units commonly possessed directing angles of ≤90°, which enabled the macrocyclization of multiple units, up to six. In this study, we introduce an obtuse-angled corner unit for the synthesis of cyclo-para-phenylene congeners. The corner unit with oxanorbornadiene possessed a directing angle of 126° and thus allowed for the macrocyclization of larger structures with up to seven units. Reductive aromatization was applicable to complete the cyclo-para-phenylene structures and afforded the congeners with multiple anthracenylene panels. Structural studies with experimental and theoretical methods revealed a fluctuating structure with an intrinsic non-belt shape.

Original languageEnglish
Pages (from-to)271-275
Number of pages5
JournalChemistry - An Asian Journal
Volume12
Issue number2
DOIs
Publication statusPublished - 2017 Jan 17

Keywords

  • anthracenylene
  • carbon nanohoop
  • macrocycles
  • oxanorbornadiene
  • structure elucidation

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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