One-shot K-region-selective annulative π-extension for nanographene synthesis and functionalization

Kyohei Ozaki, Katsuaki Kawasumi, Mari Shibata, Hideto Ito, Kenichiro Itami

Research output: Contribution to journalArticle

85 Citations (Scopus)

Abstract

The optoelectronic nature of two-dimensional sheets of sp2-hydridized carbons (for example, graphenes and nanographenes) can be dramatically altered and tuned by altering the degree of π-extension, shape, width and edge topology. Among various approaches to synthesize nanographenes with atom-by-atom precision, one-shot annulative π-extension (APEX) reactions of polycyclic aromatic hydrocarbons hold significant potential not only to achieve a 'growth from template' synthesis of nanographenes, but also to fine-tune the properties of nanographenes. Here we describe one-shot APEX reactions that occur at the K-region (convex armchair edge) of polycyclic aromatic hydrocarbons by the Pd(CH3CN)4(SbF6)2/ o-chloranil catalytic system with silicon-bridged aromatics as π-extending agents. Density functional theory calculations suggest that the complete K-region selectivity stems from the olefinic (decreased aromatic) character of the K-region. The protocol is applicable to multiple APEX and sequential APEX reactions, to construct various nanographene structures in a rapid and programmable manner.

Original languageEnglish
Article number6251
JournalNature Communications
Volume6
DOIs
Publication statusPublished - Feb 17 2015
Externally publishedYes

Fingerprint

Polycyclic Aromatic Hydrocarbons
shot
polycyclic aromatic hydrocarbons
Atoms
Silicon
synthesis
Optoelectronic devices
Density functional theory
Carbon
Topology
stems
atoms
templates
topology
Growth
selectivity
density functional theory
carbon
silicon
2-chloranil

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)
  • Chemistry(all)
  • Physics and Astronomy(all)

Cite this

One-shot K-region-selective annulative π-extension for nanographene synthesis and functionalization. / Ozaki, Kyohei; Kawasumi, Katsuaki; Shibata, Mari; Ito, Hideto; Itami, Kenichiro.

In: Nature Communications, Vol. 6, 6251, 17.02.2015.

Research output: Contribution to journalArticle

Ozaki, Kyohei ; Kawasumi, Katsuaki ; Shibata, Mari ; Ito, Hideto ; Itami, Kenichiro. / One-shot K-region-selective annulative π-extension for nanographene synthesis and functionalization. In: Nature Communications. 2015 ; Vol. 6.
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