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Synfacts 2018; 14(10): 1029
DOI: 10.1055/s-0037-1610939
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Lucky Seven-Membered Rings in N-Doped Nonplanar Nanographenes

Contributor(s):
Timothy M. Swager
,
Kosuke Yoshinaga
Oki K, Takase M. * Mori S, Shiotari A, Sugimoto Y, Ohara K, Okujima T, Uno H. * Ehime University, Matsuyama and The University of Tokyo, Kashiwa, Japan
Synthesis, Structures, and Properties of Core-Expanded Azacoronene Analogue: A Twisted π-System with Two N-Doped Heptagons.

J. Am. Chem. Soc. 2018;
140: 10430-10434
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Publication History

Publication Date:
17 September 2018 (online)

 
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Key words

azaaromatics - electronic materials - oxidation

Significance

Nanographenes containing hepta­gonal rings have received attention because of their unique electronic properties arising from their nonplanarity. Introducing heteroatoms into nano­graphenes is also known to affect their electronic nature without modifying the structure. However, heteroatom doping in nonplanar nanographenes containing heptagonal rings are not well known. Here, Takase, Uno and co-workers report a rapid two-step synthesis of a core-expanded azacoronene analogue, which possesses two heptagonal rings and eight inner nitrogen atoms.


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Comment

This electron-rich azacoronene analogue showed four reversible oxidation peaks. Single crystals of the neutral state and dicationic state could be obtained. From the bond-length alternation, nucleus-independent chemical shift and anisotropy of the induced current density calculations, the authors conclude overall Hückel aromaticity through 30π conjugation in the dicationic state, despite being nonplanar.


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