On-Surface Synthesis of a π-Extended Diaza[8]circulene

Kimihiro Nakamura, Qiang Qiang Li, Ondřej Krejčí, Adam S. Foster*, Kewei Sun, Shigeki Kawai, Shingo Ito

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

4 Citations (Scopus)

Abstract

Heterocyclic [8]circulenes are an important class of polycyclic aromatic hydrocarbon molecules because of their unique structural properties and promising applications. However, the synthesis of heterocyclic [8]circulenes is still limited and thus is an important synthetic challenge. Here we describe the first example of a π-extended diaza[8]circulene surrounded by and fused with six hexagons and two pentagons, which was successfully synthesized only by a combined in-solution and on-surface synthetic strategy. State-of-the-art scanning tunneling microscopy with a CO-functionalized tip and density functional theory calculations revealed its planar conformation and unique electronic structure.

Original languageEnglish
Pages (from-to)11363–11369
JournalJournal of the American Chemical Society
Volume142
Issue number26
Early online date1 Jan 2020
DOIs
Publication statusPublished - 15 May 2020
MoE publication typeA1 Journal article-refereed

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