A Hybrid of Corannulene and Azacorannulene: Synthesis of a Highly Curved Nitrogen-Containing Buckybowl

Yuki Tokimaru; Shingo Ito; Kyoko Nozaki

doi:10.1002/anie.201805678

A Hybrid of Corannulene and Azacorannulene: Synthesis of a Highly Curved Nitrogen-Containing Buckybowl

Yuki Tokimaru, Shingo Ito^*, Kyoko Nozaki

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

79 Citations (Scopus)

Abstract

A highly curved nitrogen-containing buckybowl, which can be considered as a corannulene/azacorannulene hybrid, was synthesized and characterized. This molecule has a polycyclic aromatic C₄₀N core, corresponding to a partial azafullerene structure C_80−xN_x (x=1,2,3…), and exhibits interesting properties that arise from its large and highly curved π surface and the embedded nitrogen atom, which include association with C₆₀, a lower LUMO level relative to azapentabenzocorannulene, and the formation of a radical cationic species upon oxidation.

Original language	English
Pages (from-to)	9818-9822
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	57
Issue number	31
DOIs	https://doi.org/10.1002/anie.201805678
Publication status	Published - Jul 26 2018
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

ASJC Scopus Subject Areas

Catalysis
General Chemistry

Keywords

1,3-dipolar cycloaddition
azacorannulene
buckybowls
corannulene
polycyclic aromatic hydrocarbons

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10.1002/anie.201805678

Cite this

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title = "A Hybrid of Corannulene and Azacorannulene: Synthesis of a Highly Curved Nitrogen-Containing Buckybowl",

abstract = "A highly curved nitrogen-containing buckybowl, which can be considered as a corannulene/azacorannulene hybrid, was synthesized and characterized. This molecule has a polycyclic aromatic C40N core, corresponding to a partial azafullerene structure C80−xNx (x=1,2,3…), and exhibits interesting properties that arise from its large and highly curved π surface and the embedded nitrogen atom, which include association with C60, a lower LUMO level relative to azapentabenzocorannulene, and the formation of a radical cationic species upon oxidation.",

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doi = "10.1002/anie.201805678",

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AU - Nozaki, Kyoko

PY - 2018/7/26

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AB - A highly curved nitrogen-containing buckybowl, which can be considered as a corannulene/azacorannulene hybrid, was synthesized and characterized. This molecule has a polycyclic aromatic C40N core, corresponding to a partial azafullerene structure C80−xNx (x=1,2,3…), and exhibits interesting properties that arise from its large and highly curved π surface and the embedded nitrogen atom, which include association with C60, a lower LUMO level relative to azapentabenzocorannulene, and the formation of a radical cationic species upon oxidation.

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KW - buckybowls

KW - corannulene

KW - polycyclic aromatic hydrocarbons

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A Hybrid of Corannulene and Azacorannulene: Synthesis of a Highly Curved Nitrogen-Containing Buckybowl

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

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