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Tridecacyclene Tetraimide: An Easily Reduced Cyclooctatetraene Derivative

Tridecacyclene tetraimide, TCTI, an electron‐deficient non‐benzenoid nanocarbon with a C(56)N(4) polycyclic framework was obtained in a concise synthesis. TCTI has a non‐planar structure and forms π‐stacked dimers in the solid state. In solution, it undergoes eight single‐electron reductions, yieldi...

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Autores principales: Kumar, Rakesh, Chmielewski, Piotr J., Lis, Tadeusz, Volkmer, Dirk, Stępień, Marcin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9545420/
https://www.ncbi.nlm.nih.gov/pubmed/35819871
http://dx.doi.org/10.1002/anie.202207486
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author Kumar, Rakesh
Chmielewski, Piotr J.
Lis, Tadeusz
Volkmer, Dirk
Stępień, Marcin
author_facet Kumar, Rakesh
Chmielewski, Piotr J.
Lis, Tadeusz
Volkmer, Dirk
Stępień, Marcin
author_sort Kumar, Rakesh
collection PubMed
description Tridecacyclene tetraimide, TCTI, an electron‐deficient non‐benzenoid nanocarbon with a C(56)N(4) polycyclic framework was obtained in a concise synthesis. TCTI has a non‐planar structure and forms π‐stacked dimers in the solid state. In solution, it undergoes eight single‐electron reductions, yielding a range of negatively charged states up to an octaanion. Except for the latter species, which has a remarkably large electronic gap, the anions feature extended near‐infrared absorptions, with a particularly strong band at 1692 nm observed for the dianion. A computational analysis of the TCTI anions shows that their stability originates from the combined effects of electron‐deficient imide groups and the local aromaticity of reduced acenaphthylene units. The properties of TCTI make it potentially useful in electrochromic and charge storage applications.
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spelling pubmed-95454202022-10-14 Tridecacyclene Tetraimide: An Easily Reduced Cyclooctatetraene Derivative Kumar, Rakesh Chmielewski, Piotr J. Lis, Tadeusz Volkmer, Dirk Stępień, Marcin Angew Chem Int Ed Engl Research Articles Tridecacyclene tetraimide, TCTI, an electron‐deficient non‐benzenoid nanocarbon with a C(56)N(4) polycyclic framework was obtained in a concise synthesis. TCTI has a non‐planar structure and forms π‐stacked dimers in the solid state. In solution, it undergoes eight single‐electron reductions, yielding a range of negatively charged states up to an octaanion. Except for the latter species, which has a remarkably large electronic gap, the anions feature extended near‐infrared absorptions, with a particularly strong band at 1692 nm observed for the dianion. A computational analysis of the TCTI anions shows that their stability originates from the combined effects of electron‐deficient imide groups and the local aromaticity of reduced acenaphthylene units. The properties of TCTI make it potentially useful in electrochromic and charge storage applications. John Wiley and Sons Inc. 2022-08-16 2022-09-19 /pmc/articles/PMC9545420/ /pubmed/35819871 http://dx.doi.org/10.1002/anie.202207486 Text en © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ (https://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Research Articles
Kumar, Rakesh
Chmielewski, Piotr J.
Lis, Tadeusz
Volkmer, Dirk
Stępień, Marcin
Tridecacyclene Tetraimide: An Easily Reduced Cyclooctatetraene Derivative
title Tridecacyclene Tetraimide: An Easily Reduced Cyclooctatetraene Derivative
title_full Tridecacyclene Tetraimide: An Easily Reduced Cyclooctatetraene Derivative
title_fullStr Tridecacyclene Tetraimide: An Easily Reduced Cyclooctatetraene Derivative
title_full_unstemmed Tridecacyclene Tetraimide: An Easily Reduced Cyclooctatetraene Derivative
title_short Tridecacyclene Tetraimide: An Easily Reduced Cyclooctatetraene Derivative
title_sort tridecacyclene tetraimide: an easily reduced cyclooctatetraene derivative
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9545420/
https://www.ncbi.nlm.nih.gov/pubmed/35819871
http://dx.doi.org/10.1002/anie.202207486
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