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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...

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Autores principales: Reger, David, Schöll, Kilian, Hampel, Frank, Maid, Harald, Jux, Norbert
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
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.
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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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