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

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 describ...

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Bibliographic Details
Main Authors: Nakamura, Kimihiro, Li, Qiang-Qiang, Krejčí, Ondřej, Foster, Adam S., Sun, Kewei, Kawai, Shigeki, Ito, Shingo
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2021
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Online Access:https://hdl.handle.net/10356/151906
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Institution: Nanyang Technological University
Language: English
Description
Summary: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.