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Aromatic Nanosandwich Obtained by σ-Dimerization of a Nanographenoid π-Radical
[Image: see text] A 139-π-electron nanographenoid radical was obtained by expanding the periphery of a naphthalimide–azacoronene hybrid with a methine bridge. The radical was isolated in the form of its σ-dimer, which was shown to possess a conformationally restricted two-layer structure both in the...
Autores principales: | , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical
Society
2020
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7467677/ https://www.ncbi.nlm.nih.gov/pubmed/31997634 http://dx.doi.org/10.1021/jacs.9b13942 |
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author | Moshniaha, Liliia Żyła-Karwowska, Marika Chmielewski, Piotr J. Lis, Tadeusz Cybińska, Joanna Gońka, Elżbieta Oschwald, Johannes Drewello, Thomas Rivero, Samara Medina Casado, Juan Stępień, Marcin |
author_facet | Moshniaha, Liliia Żyła-Karwowska, Marika Chmielewski, Piotr J. Lis, Tadeusz Cybińska, Joanna Gońka, Elżbieta Oschwald, Johannes Drewello, Thomas Rivero, Samara Medina Casado, Juan Stępień, Marcin |
author_sort | Moshniaha, Liliia |
collection | PubMed |
description | [Image: see text] A 139-π-electron nanographenoid radical was obtained by expanding the periphery of a naphthalimide–azacoronene hybrid with a methine bridge. The radical was isolated in the form of its σ-dimer, which was shown to possess a conformationally restricted two-layer structure both in the solid state and in solution. The dimer is cleaved into its parent radicals when exposed to ultraviolet or visible radiation in toluene solutions but is resistant to thermally induced dissociation. Under inert conditions, the radicals recombine quantitatively into the σ-dimer with observable kinetics, but they are oxidized into a ketone derivative in the presence of atmospheric oxygen. Combined structural, spectroscopic, and theoretical evidence shows that the σ-dimer contains a weak C(sp(3))–C(sp(3)) bond, but is stabilized against thermal dissociation by a very strong dispersive interaction between the overlapping π surfaces. |
format | Online Article Text |
id | pubmed-7467677 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | American Chemical
Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-74676772020-09-03 Aromatic Nanosandwich Obtained by σ-Dimerization of a Nanographenoid π-Radical Moshniaha, Liliia Żyła-Karwowska, Marika Chmielewski, Piotr J. Lis, Tadeusz Cybińska, Joanna Gońka, Elżbieta Oschwald, Johannes Drewello, Thomas Rivero, Samara Medina Casado, Juan Stępień, Marcin J Am Chem Soc [Image: see text] A 139-π-electron nanographenoid radical was obtained by expanding the periphery of a naphthalimide–azacoronene hybrid with a methine bridge. The radical was isolated in the form of its σ-dimer, which was shown to possess a conformationally restricted two-layer structure both in the solid state and in solution. The dimer is cleaved into its parent radicals when exposed to ultraviolet or visible radiation in toluene solutions but is resistant to thermally induced dissociation. Under inert conditions, the radicals recombine quantitatively into the σ-dimer with observable kinetics, but they are oxidized into a ketone derivative in the presence of atmospheric oxygen. Combined structural, spectroscopic, and theoretical evidence shows that the σ-dimer contains a weak C(sp(3))–C(sp(3)) bond, but is stabilized against thermal dissociation by a very strong dispersive interaction between the overlapping π surfaces. American Chemical Society 2020-01-30 2020-02-19 /pmc/articles/PMC7467677/ /pubmed/31997634 http://dx.doi.org/10.1021/jacs.9b13942 Text en Copyright © 2020 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited. |
spellingShingle | Moshniaha, Liliia Żyła-Karwowska, Marika Chmielewski, Piotr J. Lis, Tadeusz Cybińska, Joanna Gońka, Elżbieta Oschwald, Johannes Drewello, Thomas Rivero, Samara Medina Casado, Juan Stępień, Marcin Aromatic Nanosandwich Obtained by σ-Dimerization of a Nanographenoid π-Radical |
title | Aromatic
Nanosandwich Obtained by σ-Dimerization
of a Nanographenoid π-Radical |
title_full | Aromatic
Nanosandwich Obtained by σ-Dimerization
of a Nanographenoid π-Radical |
title_fullStr | Aromatic
Nanosandwich Obtained by σ-Dimerization
of a Nanographenoid π-Radical |
title_full_unstemmed | Aromatic
Nanosandwich Obtained by σ-Dimerization
of a Nanographenoid π-Radical |
title_short | Aromatic
Nanosandwich Obtained by σ-Dimerization
of a Nanographenoid π-Radical |
title_sort | aromatic
nanosandwich obtained by σ-dimerization
of a nanographenoid π-radical |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7467677/ https://www.ncbi.nlm.nih.gov/pubmed/31997634 http://dx.doi.org/10.1021/jacs.9b13942 |
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