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Persulfurated Benzene‐Cored Asterisks with π‐Extended ThioNaphthyl Arms: Synthesis, Structural, Photophysical and Covalent Dynamic Properties
The synthesis of regioisomeric asterisks (5) and (6) incorporating a benzene core with six 1‐naphthylthio or six 2‐naphthylthio arms are reported in search for new materials with optoelectronic properties. The consequences on the extension of a π system surrounding a persulfurated benzene core provi...
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/PMC9545377/ https://www.ncbi.nlm.nih.gov/pubmed/35443101 http://dx.doi.org/10.1002/chem.202200797 |
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author | Gahlot, Sapna Gradone, Alessandro Roy, Myriam Giorgi, Michel Conti, Simone Ceroni, Paola Villa, Marco Gingras, Marc |
author_facet | Gahlot, Sapna Gradone, Alessandro Roy, Myriam Giorgi, Michel Conti, Simone Ceroni, Paola Villa, Marco Gingras, Marc |
author_sort | Gahlot, Sapna |
collection | PubMed |
description | The synthesis of regioisomeric asterisks (5) and (6) incorporating a benzene core with six 1‐naphthylthio or six 2‐naphthylthio arms are reported in search for new materials with optoelectronic properties. The consequences on the extension of a π system surrounding a persulfurated benzene core provide a new avenue to study the structural, photophysical, and chemical properties of such family of all‐organic phosphors. It also diverts the persulfuration mechanism after two radical cyclizations for making a [5]dithiohelicene by‐product (7) and favors dynamic sulfur component exchange reactions surrounding the core. These exchanges convert asterisks (5) and (6), non‐phosphorescent at 20 °C to the highly phosphorescent (4) (ϕ ∼100 %, solid state at 20 °C). For asterisks (5) and (6), the absence of the typical phosphorescence of the per(phenylthio)benzene core in the solid state at 20 °C and the presence of a weak naphthalene‐based phosphorescence at 77 K is attributed to an energy transfer from the triplet state of the persulfurated benzene core to the outer naphthalene moieties, resulting in an antenna system. |
format | Online Article Text |
id | pubmed-9545377 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-95453772022-10-14 Persulfurated Benzene‐Cored Asterisks with π‐Extended ThioNaphthyl Arms: Synthesis, Structural, Photophysical and Covalent Dynamic Properties Gahlot, Sapna Gradone, Alessandro Roy, Myriam Giorgi, Michel Conti, Simone Ceroni, Paola Villa, Marco Gingras, Marc Chemistry Research Articles The synthesis of regioisomeric asterisks (5) and (6) incorporating a benzene core with six 1‐naphthylthio or six 2‐naphthylthio arms are reported in search for new materials with optoelectronic properties. The consequences on the extension of a π system surrounding a persulfurated benzene core provide a new avenue to study the structural, photophysical, and chemical properties of such family of all‐organic phosphors. It also diverts the persulfuration mechanism after two radical cyclizations for making a [5]dithiohelicene by‐product (7) and favors dynamic sulfur component exchange reactions surrounding the core. These exchanges convert asterisks (5) and (6), non‐phosphorescent at 20 °C to the highly phosphorescent (4) (ϕ ∼100 %, solid state at 20 °C). For asterisks (5) and (6), the absence of the typical phosphorescence of the per(phenylthio)benzene core in the solid state at 20 °C and the presence of a weak naphthalene‐based phosphorescence at 77 K is attributed to an energy transfer from the triplet state of the persulfurated benzene core to the outer naphthalene moieties, resulting in an antenna system. John Wiley and Sons Inc. 2022-06-27 2022-08-16 /pmc/articles/PMC9545377/ /pubmed/35443101 http://dx.doi.org/10.1002/chem.202200797 Text en © 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ (https://creativecommons.org/licenses/by-nc/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes. |
spellingShingle | Research Articles Gahlot, Sapna Gradone, Alessandro Roy, Myriam Giorgi, Michel Conti, Simone Ceroni, Paola Villa, Marco Gingras, Marc Persulfurated Benzene‐Cored Asterisks with π‐Extended ThioNaphthyl Arms: Synthesis, Structural, Photophysical and Covalent Dynamic Properties |
title | Persulfurated Benzene‐Cored Asterisks with π‐Extended ThioNaphthyl Arms: Synthesis, Structural, Photophysical and Covalent Dynamic Properties |
title_full | Persulfurated Benzene‐Cored Asterisks with π‐Extended ThioNaphthyl Arms: Synthesis, Structural, Photophysical and Covalent Dynamic Properties |
title_fullStr | Persulfurated Benzene‐Cored Asterisks with π‐Extended ThioNaphthyl Arms: Synthesis, Structural, Photophysical and Covalent Dynamic Properties |
title_full_unstemmed | Persulfurated Benzene‐Cored Asterisks with π‐Extended ThioNaphthyl Arms: Synthesis, Structural, Photophysical and Covalent Dynamic Properties |
title_short | Persulfurated Benzene‐Cored Asterisks with π‐Extended ThioNaphthyl Arms: Synthesis, Structural, Photophysical and Covalent Dynamic Properties |
title_sort | persulfurated benzene‐cored asterisks with π‐extended thionaphthyl arms: synthesis, structural, photophysical and covalent dynamic properties |
topic | Research Articles |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9545377/ https://www.ncbi.nlm.nih.gov/pubmed/35443101 http://dx.doi.org/10.1002/chem.202200797 |
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