Cargando…

Thermally Induced Synthesis of Anthracene‐, Pyrene‐ and Naphthalene‐Fused Porphyrins

The synthesis of π‐extended porphyrins containing anthracenyl moieties still represents an important challenge. Here, we report on the synthesis of a series of unsubstituted naphthyl‐, pyrenyl‐ and anthracenyl‐fused zinc porphyrin derivatives. To this aim, meso‐substitued porphyrins are synthesized...

Descripción completa

Detalles Bibliográficos
Autores principales: Pijeat, Joffrey, Chaussy, Léo, Simoës, Roxanne, Isopi, Jacopo, Lauret, Jean‐Sébastien, Paolucci, Francesco, Marcaccio, Massimo, Campidelli, Stéphane
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8495684/
https://www.ncbi.nlm.nih.gov/pubmed/34617692
http://dx.doi.org/10.1002/open.202100201
_version_ 1784579597891796992
author Pijeat, Joffrey
Chaussy, Léo
Simoës, Roxanne
Isopi, Jacopo
Lauret, Jean‐Sébastien
Paolucci, Francesco
Marcaccio, Massimo
Campidelli, Stéphane
author_facet Pijeat, Joffrey
Chaussy, Léo
Simoës, Roxanne
Isopi, Jacopo
Lauret, Jean‐Sébastien
Paolucci, Francesco
Marcaccio, Massimo
Campidelli, Stéphane
author_sort Pijeat, Joffrey
collection PubMed
description The synthesis of π‐extended porphyrins containing anthracenyl moieties still represents an important challenge. Here, we report on the synthesis of a series of unsubstituted naphthyl‐, pyrenyl‐ and anthracenyl‐fused zinc porphyrin derivatives. To this aim, meso‐substitued porphyrins are synthesized and the fusion of the PAHs (Polycyclic Aromatic Hydrocarbon) on the β‐positions are performed through thermally induced dehydro‐aromatization. The fused zinc‐porphyrin derivatives are fully characterized and their optical absorption and photoluminescence properties are reported. We also demonstrate that zinc can be removed from the porphyrin core, giving rise to pure C, H, N materials. This work constitutes the first step towards the synthesis of the fully‐fused tetra‐anthracenylporphyrin.
format Online
Article
Text
id pubmed-8495684
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher John Wiley and Sons Inc.
record_format MEDLINE/PubMed
spelling pubmed-84956842021-10-08 Thermally Induced Synthesis of Anthracene‐, Pyrene‐ and Naphthalene‐Fused Porphyrins Pijeat, Joffrey Chaussy, Léo Simoës, Roxanne Isopi, Jacopo Lauret, Jean‐Sébastien Paolucci, Francesco Marcaccio, Massimo Campidelli, Stéphane ChemistryOpen Full Papers The synthesis of π‐extended porphyrins containing anthracenyl moieties still represents an important challenge. Here, we report on the synthesis of a series of unsubstituted naphthyl‐, pyrenyl‐ and anthracenyl‐fused zinc porphyrin derivatives. To this aim, meso‐substitued porphyrins are synthesized and the fusion of the PAHs (Polycyclic Aromatic Hydrocarbon) on the β‐positions are performed through thermally induced dehydro‐aromatization. The fused zinc‐porphyrin derivatives are fully characterized and their optical absorption and photoluminescence properties are reported. We also demonstrate that zinc can be removed from the porphyrin core, giving rise to pure C, H, N materials. This work constitutes the first step towards the synthesis of the fully‐fused tetra‐anthracenylporphyrin. John Wiley and Sons Inc. 2021-10-07 /pmc/articles/PMC8495684/ /pubmed/34617692 http://dx.doi.org/10.1002/open.202100201 Text en © 2021 The Authors. 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 Full Papers
Pijeat, Joffrey
Chaussy, Léo
Simoës, Roxanne
Isopi, Jacopo
Lauret, Jean‐Sébastien
Paolucci, Francesco
Marcaccio, Massimo
Campidelli, Stéphane
Thermally Induced Synthesis of Anthracene‐, Pyrene‐ and Naphthalene‐Fused Porphyrins
title Thermally Induced Synthesis of Anthracene‐, Pyrene‐ and Naphthalene‐Fused Porphyrins
title_full Thermally Induced Synthesis of Anthracene‐, Pyrene‐ and Naphthalene‐Fused Porphyrins
title_fullStr Thermally Induced Synthesis of Anthracene‐, Pyrene‐ and Naphthalene‐Fused Porphyrins
title_full_unstemmed Thermally Induced Synthesis of Anthracene‐, Pyrene‐ and Naphthalene‐Fused Porphyrins
title_short Thermally Induced Synthesis of Anthracene‐, Pyrene‐ and Naphthalene‐Fused Porphyrins
title_sort thermally induced synthesis of anthracene‐, pyrene‐ and naphthalene‐fused porphyrins
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8495684/
https://www.ncbi.nlm.nih.gov/pubmed/34617692
http://dx.doi.org/10.1002/open.202100201
work_keys_str_mv AT pijeatjoffrey thermallyinducedsynthesisofanthracenepyreneandnaphthalenefusedporphyrins
AT chaussyleo thermallyinducedsynthesisofanthracenepyreneandnaphthalenefusedporphyrins
AT simoesroxanne thermallyinducedsynthesisofanthracenepyreneandnaphthalenefusedporphyrins
AT isopijacopo thermallyinducedsynthesisofanthracenepyreneandnaphthalenefusedporphyrins
AT lauretjeansebastien thermallyinducedsynthesisofanthracenepyreneandnaphthalenefusedporphyrins
AT paoluccifrancesco thermallyinducedsynthesisofanthracenepyreneandnaphthalenefusedporphyrins
AT marcacciomassimo thermallyinducedsynthesisofanthracenepyreneandnaphthalenefusedporphyrins
AT campidellistephane thermallyinducedsynthesisofanthracenepyreneandnaphthalenefusedporphyrins