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Controlling the helicity of π-conjugated oligomers by tuning the aromatic backbone twist
The properties of π-conjugated oligomers and polymers are commonly controlled by side group engineering, main chain engineering, or conformational engineering. The last approach is typically limited to controlling the dihedral angle around the interring single bonds to prevent loss of π-conjugation....
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group UK
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8782941/ https://www.ncbi.nlm.nih.gov/pubmed/35064118 http://dx.doi.org/10.1038/s41467-022-28072-7 |
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author | Bedi, Anjan Manor Armon, Amit Diskin-Posner, Yael Bogosalvsky, Benny Gidron, Ori |
author_facet | Bedi, Anjan Manor Armon, Amit Diskin-Posner, Yael Bogosalvsky, Benny Gidron, Ori |
author_sort | Bedi, Anjan |
collection | PubMed |
description | The properties of π-conjugated oligomers and polymers are commonly controlled by side group engineering, main chain engineering, or conformational engineering. The last approach is typically limited to controlling the dihedral angle around the interring single bonds to prevent loss of π-conjugation. Here we propose a different approach to conformational engineering that involves controlling the twist of the aromatic units comprising the backbone by using a tether of varying lengths. We demonstrate this approach by synthesizing an inherently twisted building unit comprised of helically locked tethered acenes, bearing acetylene end-groups to enable backbone extension, which was applied in a series of nine helical oligomers with varying backbone length and twist. We find that the optical and electronic properties of π-conjugated systems may be determined by the additive, antagonistic, or independent effects of backbone length and twist angle. The twisted oligomers display chiral amplification, arising from the formation of secondary helical structures. |
format | Online Article Text |
id | pubmed-8782941 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | Nature Publishing Group UK |
record_format | MEDLINE/PubMed |
spelling | pubmed-87829412022-02-04 Controlling the helicity of π-conjugated oligomers by tuning the aromatic backbone twist Bedi, Anjan Manor Armon, Amit Diskin-Posner, Yael Bogosalvsky, Benny Gidron, Ori Nat Commun Article The properties of π-conjugated oligomers and polymers are commonly controlled by side group engineering, main chain engineering, or conformational engineering. The last approach is typically limited to controlling the dihedral angle around the interring single bonds to prevent loss of π-conjugation. Here we propose a different approach to conformational engineering that involves controlling the twist of the aromatic units comprising the backbone by using a tether of varying lengths. We demonstrate this approach by synthesizing an inherently twisted building unit comprised of helically locked tethered acenes, bearing acetylene end-groups to enable backbone extension, which was applied in a series of nine helical oligomers with varying backbone length and twist. We find that the optical and electronic properties of π-conjugated systems may be determined by the additive, antagonistic, or independent effects of backbone length and twist angle. The twisted oligomers display chiral amplification, arising from the formation of secondary helical structures. Nature Publishing Group UK 2022-01-21 /pmc/articles/PMC8782941/ /pubmed/35064118 http://dx.doi.org/10.1038/s41467-022-28072-7 Text en © The Author(s) 2022 https://creativecommons.org/licenses/by/4.0/Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) . |
spellingShingle | Article Bedi, Anjan Manor Armon, Amit Diskin-Posner, Yael Bogosalvsky, Benny Gidron, Ori Controlling the helicity of π-conjugated oligomers by tuning the aromatic backbone twist |
title | Controlling the helicity of π-conjugated oligomers by tuning the aromatic backbone twist |
title_full | Controlling the helicity of π-conjugated oligomers by tuning the aromatic backbone twist |
title_fullStr | Controlling the helicity of π-conjugated oligomers by tuning the aromatic backbone twist |
title_full_unstemmed | Controlling the helicity of π-conjugated oligomers by tuning the aromatic backbone twist |
title_short | Controlling the helicity of π-conjugated oligomers by tuning the aromatic backbone twist |
title_sort | controlling the helicity of π-conjugated oligomers by tuning the aromatic backbone twist |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8782941/ https://www.ncbi.nlm.nih.gov/pubmed/35064118 http://dx.doi.org/10.1038/s41467-022-28072-7 |
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