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N-doped nonalternant aromatic belt via a six-fold annulative double N-arylation

The design and synthesis of nitrogen (N)-doped molecular nanocarbons are of importance since N-doped nanocarbons have received significant attention in materials science. Herein, we report the synthesis and X-ray crystal structure of a nitrogen-inserted nonalternant aromatic belt. The palladium-cata...

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Autores principales: Sato, Hiroki, Suizu, Rie, Kato, Tomoki, Yagi, Akiko, Segawa, Yasutomo, Awaga, Kunio, Itami, Kenichiro
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9430306/
https://www.ncbi.nlm.nih.gov/pubmed/36128250
http://dx.doi.org/10.1039/d2sc02647c
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author Sato, Hiroki
Suizu, Rie
Kato, Tomoki
Yagi, Akiko
Segawa, Yasutomo
Awaga, Kunio
Itami, Kenichiro
author_facet Sato, Hiroki
Suizu, Rie
Kato, Tomoki
Yagi, Akiko
Segawa, Yasutomo
Awaga, Kunio
Itami, Kenichiro
author_sort Sato, Hiroki
collection PubMed
description The design and synthesis of nitrogen (N)-doped molecular nanocarbons are of importance since N-doped nanocarbons have received significant attention in materials science. Herein, we report the synthesis and X-ray crystal structure of a nitrogen-inserted nonalternant aromatic belt. The palladium-catalyzed six-fold annulative double N-arylation provided an aromatic belt bearing six nitrogen atoms in one step from cyclo[6]paraphenylene-Z-ethenylene, the precursor of the (6,6)carbon nanobelt. The C(3i)-symmetric structure of the aromatic belt in the solid state was revealed using X-ray crystallography. The multistep (electro)chemical oxidation behavior of the belt, which was facilitated by the six p-methoxyaniline moieties, was studied, and a stable dication species was successfully identified by X-ray crystallography. The present study not only shows the unique structure and properties of the N-doped nonalternant aromatic belt but also expands the scope of accessibility of synthetically difficult belt molecules by the conventional intramolecular contraction pathway.
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spelling pubmed-94303062022-09-19 N-doped nonalternant aromatic belt via a six-fold annulative double N-arylation Sato, Hiroki Suizu, Rie Kato, Tomoki Yagi, Akiko Segawa, Yasutomo Awaga, Kunio Itami, Kenichiro Chem Sci Chemistry The design and synthesis of nitrogen (N)-doped molecular nanocarbons are of importance since N-doped nanocarbons have received significant attention in materials science. Herein, we report the synthesis and X-ray crystal structure of a nitrogen-inserted nonalternant aromatic belt. The palladium-catalyzed six-fold annulative double N-arylation provided an aromatic belt bearing six nitrogen atoms in one step from cyclo[6]paraphenylene-Z-ethenylene, the precursor of the (6,6)carbon nanobelt. The C(3i)-symmetric structure of the aromatic belt in the solid state was revealed using X-ray crystallography. The multistep (electro)chemical oxidation behavior of the belt, which was facilitated by the six p-methoxyaniline moieties, was studied, and a stable dication species was successfully identified by X-ray crystallography. The present study not only shows the unique structure and properties of the N-doped nonalternant aromatic belt but also expands the scope of accessibility of synthetically difficult belt molecules by the conventional intramolecular contraction pathway. The Royal Society of Chemistry 2022-08-09 /pmc/articles/PMC9430306/ /pubmed/36128250 http://dx.doi.org/10.1039/d2sc02647c Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Sato, Hiroki
Suizu, Rie
Kato, Tomoki
Yagi, Akiko
Segawa, Yasutomo
Awaga, Kunio
Itami, Kenichiro
N-doped nonalternant aromatic belt via a six-fold annulative double N-arylation
title N-doped nonalternant aromatic belt via a six-fold annulative double N-arylation
title_full N-doped nonalternant aromatic belt via a six-fold annulative double N-arylation
title_fullStr N-doped nonalternant aromatic belt via a six-fold annulative double N-arylation
title_full_unstemmed N-doped nonalternant aromatic belt via a six-fold annulative double N-arylation
title_short N-doped nonalternant aromatic belt via a six-fold annulative double N-arylation
title_sort n-doped nonalternant aromatic belt via a six-fold annulative double n-arylation
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9430306/
https://www.ncbi.nlm.nih.gov/pubmed/36128250
http://dx.doi.org/10.1039/d2sc02647c
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