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

Author

Listed:
  • Kyohei Ozaki

    (Institute of Transformative Bio-Molecules (WPI-ITbM) and Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan)

  • Katsuaki Kawasumi

    (Institute of Transformative Bio-Molecules (WPI-ITbM) and Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan)

  • Mari Shibata

    (Institute of Transformative Bio-Molecules (WPI-ITbM) and Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan)

  • Hideto Ito

    (Institute of Transformative Bio-Molecules (WPI-ITbM) and Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan)

  • Kenichiro Itami

    (Institute of Transformative Bio-Molecules (WPI-ITbM) and Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan
    JST-ERATO, Itami Molecular Nanocarbon Project, Nagoya University, Chikusa, Nagoya 464-8602, Japan)

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.

Suggested Citation

  • Kyohei Ozaki & Katsuaki Kawasumi & Mari Shibata & Hideto Ito & Kenichiro Itami, 2015. "One-shot K-region-selective annulative π-extension for nanographene synthesis and functionalization," Nature Communications, Nature, vol. 6(1), pages 1-8, May.
    • Handle: RePEc:nat:natcom:v:6:y:2015:i:1:d:10.1038_ncomms7251
    DOI: 10.1038/ncomms7251
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    Cited by:

    1. Jae Bin Lee & Gun Ha Kim & Ji Hwan Jeon & Seo Yeong Jeong & Soochan Lee & Jaehyun Park & Doyoung Lee & Youngkook Kwon & Jeong Kon Seo & Joong-Hyun Chun & Seok Ju Kang & Wonyoung Choe & Jan-Uwe Rohde &, 2022. "Rapid access to polycyclic N-heteroarenes from unactivated, simple azines via a base-promoted Minisci-type annulation," Nature Communications, Nature, vol. 13(1), pages 1-9, December.

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