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Synthesis and Properties of NitroHPHAC: The First Example of Substitution Reaction on HPHAC
Hexapyrrolohexaazacoronene (HPHAC) is one of the N-containing polycyclic aromatic hydrocarbons in which six pyrroles are fused circularly around a benzene. Despite the recent development of HPHAC analogues, there is no report on direct introduction of functional groups into the HPHAC skeleton. This...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7321187/ https://www.ncbi.nlm.nih.gov/pubmed/32471200 http://dx.doi.org/10.3390/molecules25112486 |
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author | Sasaki, Yoshiki Takase, Masayoshi Mori, Shigeki Uno, Hidemitsu |
author_facet | Sasaki, Yoshiki Takase, Masayoshi Mori, Shigeki Uno, Hidemitsu |
author_sort | Sasaki, Yoshiki |
collection | PubMed |
description | Hexapyrrolohexaazacoronene (HPHAC) is one of the N-containing polycyclic aromatic hydrocarbons in which six pyrroles are fused circularly around a benzene. Despite the recent development of HPHAC analogues, there is no report on direct introduction of functional groups into the HPHAC skeleton. This work reports the first example of nitration reaction of decaethylHPHAC. The structures of nitrodecaethylHPHAC including neutral and two oxidized species (radical cation and dication), intramolecular charge transfer (ICT) character, and global aromaticity of the dication are discussed. |
format | Online Article Text |
id | pubmed-7321187 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-73211872020-07-06 Synthesis and Properties of NitroHPHAC: The First Example of Substitution Reaction on HPHAC Sasaki, Yoshiki Takase, Masayoshi Mori, Shigeki Uno, Hidemitsu Molecules Communication Hexapyrrolohexaazacoronene (HPHAC) is one of the N-containing polycyclic aromatic hydrocarbons in which six pyrroles are fused circularly around a benzene. Despite the recent development of HPHAC analogues, there is no report on direct introduction of functional groups into the HPHAC skeleton. This work reports the first example of nitration reaction of decaethylHPHAC. The structures of nitrodecaethylHPHAC including neutral and two oxidized species (radical cation and dication), intramolecular charge transfer (ICT) character, and global aromaticity of the dication are discussed. MDPI 2020-05-27 /pmc/articles/PMC7321187/ /pubmed/32471200 http://dx.doi.org/10.3390/molecules25112486 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Communication Sasaki, Yoshiki Takase, Masayoshi Mori, Shigeki Uno, Hidemitsu Synthesis and Properties of NitroHPHAC: The First Example of Substitution Reaction on HPHAC |
title | Synthesis and Properties of NitroHPHAC: The First Example of Substitution Reaction on HPHAC |
title_full | Synthesis and Properties of NitroHPHAC: The First Example of Substitution Reaction on HPHAC |
title_fullStr | Synthesis and Properties of NitroHPHAC: The First Example of Substitution Reaction on HPHAC |
title_full_unstemmed | Synthesis and Properties of NitroHPHAC: The First Example of Substitution Reaction on HPHAC |
title_short | Synthesis and Properties of NitroHPHAC: The First Example of Substitution Reaction on HPHAC |
title_sort | synthesis and properties of nitrohphac: the first example of substitution reaction on hphac |
topic | Communication |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7321187/ https://www.ncbi.nlm.nih.gov/pubmed/32471200 http://dx.doi.org/10.3390/molecules25112486 |
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