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Pyridinic Nanographenes by Novel Precursor Design
In this work we present the solution‐synthesis of pyridine analogues to hexa‐peri‐hexabenzocoronene (HBC)—which might be called superpyridines—via a novel precursor design. The key step in our strategy was the pre‐formation of the C−C bonds between the 3/3’ positions of the pyridine and the adjacent...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7898602/ https://www.ncbi.nlm.nih.gov/pubmed/33225488 http://dx.doi.org/10.1002/chem.202004983 |
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author | Reger, David Schöll, Kilian Hampel, Frank Maid, Harald Jux, Norbert |
author_facet | Reger, David Schöll, Kilian Hampel, Frank Maid, Harald Jux, Norbert |
author_sort | Reger, David |
collection | PubMed |
description | In this work we present the solution‐synthesis of pyridine analogues to hexa‐peri‐hexabenzocoronene (HBC)—which might be called superpyridines—via a novel precursor design. The key step in our strategy was the pre‐formation of the C−C bonds between the 3/3’ positions of the pyridine and the adjacent phenyl rings—bonds that are otherwise unreactive and difficult to close under Scholl‐conditions. Apart from the synthesis of the parent compound we show that classical pyridine chemistry, namely oxidation, N‐alkylation and metal‐coordination is applicable to the π‐extended analogue. Furthermore, we present basic physical chemical characterizations of the newly synthesized molecules. With this novel synthetic strategy, we hope to unlock the pyridine chemistry of nanographenes. |
format | Online Article Text |
id | pubmed-7898602 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-78986022021-03-03 Pyridinic Nanographenes by Novel Precursor Design Reger, David Schöll, Kilian Hampel, Frank Maid, Harald Jux, Norbert Chemistry Communications In this work we present the solution‐synthesis of pyridine analogues to hexa‐peri‐hexabenzocoronene (HBC)—which might be called superpyridines—via a novel precursor design. The key step in our strategy was the pre‐formation of the C−C bonds between the 3/3’ positions of the pyridine and the adjacent phenyl rings—bonds that are otherwise unreactive and difficult to close under Scholl‐conditions. Apart from the synthesis of the parent compound we show that classical pyridine chemistry, namely oxidation, N‐alkylation and metal‐coordination is applicable to the π‐extended analogue. Furthermore, we present basic physical chemical characterizations of the newly synthesized molecules. With this novel synthetic strategy, we hope to unlock the pyridine chemistry of nanographenes. John Wiley and Sons Inc. 2021-01-12 2021-01-26 /pmc/articles/PMC7898602/ /pubmed/33225488 http://dx.doi.org/10.1002/chem.202004983 Text en © 2020 The Authors. Published by Wiley-VCH GmbH This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Communications Reger, David Schöll, Kilian Hampel, Frank Maid, Harald Jux, Norbert Pyridinic Nanographenes by Novel Precursor Design |
title | Pyridinic Nanographenes by Novel Precursor Design |
title_full | Pyridinic Nanographenes by Novel Precursor Design |
title_fullStr | Pyridinic Nanographenes by Novel Precursor Design |
title_full_unstemmed | Pyridinic Nanographenes by Novel Precursor Design |
title_short | Pyridinic Nanographenes by Novel Precursor Design |
title_sort | pyridinic nanographenes by novel precursor design |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7898602/ https://www.ncbi.nlm.nih.gov/pubmed/33225488 http://dx.doi.org/10.1002/chem.202004983 |
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