Synthesis, Properties, and Packing Structures of Corannulene-Based π-Systems Containing Heptagons

Kenta Kato, Yasutomo Segawa, Lawrence T. Scott, Kenichiro Itami

Research output: Contribution to journalArticlepeer-review

36 Citations (Scopus)

Abstract

Introduction of heptagons into hexagonal carbon lattices can generate negatively curved polycyclic aromatic hydrocarbons, which are of significant interest in the field of exotic molecular nanocarbons. We have successfully synthesized and characterized corannulene-based π-systems containing heptagons (4 and 5) as new negatively curved polycyclic aromatic hydrocarbons as well as possible intermediates in the synthesis of warped nanographene 1. The formation of 4 and 5 represents the first example for which a heptagon is formed under Scholl reaction conditions before all hexagons are formed. Even more interestingly, we discovered that the mode and degree of solid-phase intermolecular π-π interaction can be altered significantly by the degree of ring closure.

Original languageEnglish
Pages (from-to)1635-1639
Number of pages5
JournalChemistry - An Asian Journal
Volume10
Issue number8
DOIs
Publication statusPublished - 2015 Aug 1
Externally publishedYes

Keywords

  • Scholl reaction
  • fused ring systems
  • negative curvature
  • polycyclic aromatic hydrocarbons
  • warped nanographene

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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