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Helical Bilayer Nonbenzenoid Nanographene Bearing a [10]Helicene with Two Embedded Heptagons
The precision synthesis of helical bilayer nanographenes (NGs) with new topology is of substantial interest because of their exotic physicochemical properties. However, helical bilayer NGs bearing non‐hexagonal rings remain synthetically challenging. Here we present the efficient synthesis of the fi...
Autores principales: | , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10107200/ https://www.ncbi.nlm.nih.gov/pubmed/36413379 http://dx.doi.org/10.1002/anie.202216193 |
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author | Yang, Lin Ju, Yang‐Yang Medel, Miguel A. Fu, Yubin Komber, Hartmut Dmitrieva, Evgenia Zhang, Jin‐Jiang Obermann, Sebastian Campaña, Araceli G. Ma, Ji Feng, Xinliang |
author_facet | Yang, Lin Ju, Yang‐Yang Medel, Miguel A. Fu, Yubin Komber, Hartmut Dmitrieva, Evgenia Zhang, Jin‐Jiang Obermann, Sebastian Campaña, Araceli G. Ma, Ji Feng, Xinliang |
author_sort | Yang, Lin |
collection | PubMed |
description | The precision synthesis of helical bilayer nanographenes (NGs) with new topology is of substantial interest because of their exotic physicochemical properties. However, helical bilayer NGs bearing non‐hexagonal rings remain synthetically challenging. Here we present the efficient synthesis of the first helical bilayer nonbenzenoid nanographene (HBNG1) from a tailor‐made azulene‐embedded precursor, which contains a novel [10]helicene backbone with two embedded heptagons. Single‐crystal X‐ray analysis reveals its highly twisted bilayer geometry with a record small interlayer distance of 3.2 Å among the reported helical bilayer NGs. Notably, the close interlayer distance between the two layers offers intramolecular through‐space conjugation as revealed by in situ spectroelectrochemistry studies together with DFT simulations. Furthermore, the chiroptical properties of the P/M enantiomers of HBNG1 are also evaluated by circular dichroism and circularly polarized luminescence. |
format | Online Article Text |
id | pubmed-10107200 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-101072002023-04-18 Helical Bilayer Nonbenzenoid Nanographene Bearing a [10]Helicene with Two Embedded Heptagons Yang, Lin Ju, Yang‐Yang Medel, Miguel A. Fu, Yubin Komber, Hartmut Dmitrieva, Evgenia Zhang, Jin‐Jiang Obermann, Sebastian Campaña, Araceli G. Ma, Ji Feng, Xinliang Angew Chem Int Ed Engl Communications The precision synthesis of helical bilayer nanographenes (NGs) with new topology is of substantial interest because of their exotic physicochemical properties. However, helical bilayer NGs bearing non‐hexagonal rings remain synthetically challenging. Here we present the efficient synthesis of the first helical bilayer nonbenzenoid nanographene (HBNG1) from a tailor‐made azulene‐embedded precursor, which contains a novel [10]helicene backbone with two embedded heptagons. Single‐crystal X‐ray analysis reveals its highly twisted bilayer geometry with a record small interlayer distance of 3.2 Å among the reported helical bilayer NGs. Notably, the close interlayer distance between the two layers offers intramolecular through‐space conjugation as revealed by in situ spectroelectrochemistry studies together with DFT simulations. Furthermore, the chiroptical properties of the P/M enantiomers of HBNG1 are also evaluated by circular dichroism and circularly polarized luminescence. John Wiley and Sons Inc. 2022-12-20 2023-01-23 /pmc/articles/PMC10107200/ /pubmed/36413379 http://dx.doi.org/10.1002/anie.202216193 Text en © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://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 Yang, Lin Ju, Yang‐Yang Medel, Miguel A. Fu, Yubin Komber, Hartmut Dmitrieva, Evgenia Zhang, Jin‐Jiang Obermann, Sebastian Campaña, Araceli G. Ma, Ji Feng, Xinliang Helical Bilayer Nonbenzenoid Nanographene Bearing a [10]Helicene with Two Embedded Heptagons |
title | Helical Bilayer Nonbenzenoid Nanographene Bearing a [10]Helicene with Two Embedded Heptagons |
title_full | Helical Bilayer Nonbenzenoid Nanographene Bearing a [10]Helicene with Two Embedded Heptagons |
title_fullStr | Helical Bilayer Nonbenzenoid Nanographene Bearing a [10]Helicene with Two Embedded Heptagons |
title_full_unstemmed | Helical Bilayer Nonbenzenoid Nanographene Bearing a [10]Helicene with Two Embedded Heptagons |
title_short | Helical Bilayer Nonbenzenoid Nanographene Bearing a [10]Helicene with Two Embedded Heptagons |
title_sort | helical bilayer nonbenzenoid nanographene bearing a [10]helicene with two embedded heptagons |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10107200/ https://www.ncbi.nlm.nih.gov/pubmed/36413379 http://dx.doi.org/10.1002/anie.202216193 |
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