Thermally Induced Synthesis of Anthracene-, Pyrene- and Naphthalene-Fused Porphyrins.

NIR dyes anthracene fused porphyrin polycyclic aromatic hydrocarbons thermal cyclodehydrogenation

Journal

ChemistryOpen
ISSN: 2191-1363
Titre abrégé: ChemistryOpen
Pays: Germany
ID NLM: 101594811

Informations de publication

Date de publication:
10 2021
Historique:
revised: 07 09 2021
received: 25 08 2021
entrez: 7 10 2021
pubmed: 8 10 2021
medline: 8 10 2021
Statut: ppublish

Résumé

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.

Identifiants

pubmed: 34617692
doi: 10.1002/open.202100201
pmc: PMC8495684
doi:

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

997-1003

Subventions

Organisme : ANR
ID : ANR-16-CE29-0027-01
Organisme : ANR-DFG
ID : ANR-19-CE09-0031-02
Organisme : FLAG-ERA Joint Transnational Call OPERA
ID : FLAG-ERA JTC 2019
Organisme : French National Research Agency
ID : ANR-10-LABX-0035

Informations de copyright

© 2021 The Authors. Published by Wiley-VCH GmbH.

Références

Chem Sci. 2020 Oct 26;12(1):247-252
pubmed: 34163593
Chemistry. 2014 Jul 14;20(29):8948-53
pubmed: 24966033
Angew Chem Int Ed Engl. 2018 Aug 27;57(35):11233-11237
pubmed: 29984483
Chem Commun (Camb). 2004 Jun 7;(11):1322-3
pubmed: 15154057
Sci Adv. 2018 Feb 16;4(2):eaaq0582
pubmed: 29464209
Chem Commun (Camb). 2007 May 28;(20):2069-71
pubmed: 17713081
Angew Chem Int Ed Engl. 2020 Jan 13;59(3):1334-1339
pubmed: 31729821
Chemistry. 2015 Aug 24;21(35):12285-90
pubmed: 26211450
J Phys Chem A. 2010 Nov 25;114(46):12299-304
pubmed: 21028773
Org Biomol Chem. 2011 Dec 7;9(23):8178-81
pubmed: 21997344
J Chem Inf Model. 2013 May 24;53(5):1223-8
pubmed: 23480664
Angew Chem Int Ed Engl. 2010 Jul 26;49(32):5523-6
pubmed: 20602395
J Am Chem Soc. 2020 Oct 21;142(42):18109-18117
pubmed: 32985889
Org Lett. 2010 May 7;12(9):2124-7
pubmed: 20369826
Chem Commun (Camb). 2016 Jan 31;52(9):1949-52
pubmed: 26686757
Chem Commun (Camb). 2003 Jan 7;(1):148-9
pubmed: 12611009
J Am Chem Soc. 2020 Oct 28;142(43):18532-18540
pubmed: 32959653
Angew Chem Int Ed Engl. 2006 Jun 12;45(24):3944-7
pubmed: 16683296
Phys Chem Chem Phys. 2010 Mar 14;12(10):2427-37
pubmed: 20449356
J Am Chem Soc. 2011 Jan 12;133(1):30-1
pubmed: 21141995
J Org Chem. 2012 Jan 6;77(1):143-59
pubmed: 22077105
J Am Chem Soc. 2008 Mar 26;130(12):3788-96
pubmed: 18314972
J Phys Chem B. 2009 Feb 19;113(7):1954-62
pubmed: 19173564
J Org Chem. 2011 Jan 21;76(2):661-4
pubmed: 21192635
Org Lett. 2008 Sep 18;10(18):3945-7
pubmed: 18722461

Auteurs

Joffrey Pijeat (J)

Université Paris-Saclay, CEA, CNRS, NIMBE, LICSEN, 91191, Gif-sur-Yvette, France.

Léo Chaussy (L)

Université Paris-Saclay, CEA, CNRS, NIMBE, LICSEN, 91191, Gif-sur-Yvette, France.

Roxanne Simoës (R)

Université Paris-Saclay, CEA, CNRS, NIMBE, LICSEN, 91191, Gif-sur-Yvette, France.

Jacopo Isopi (J)

Dipartimento di Chimica "Giacomo Ciamician", Università di Bologna, via Selmi 2, 40126, Bologna, Italy.

Jean-Sébastien Lauret (JS)

Université Paris Saclay, ENS Paris-Saclay, Centrale Supelec, CNRS, LUMIN, 91405, Orsay Cedex, France.

Francesco Paolucci (F)

Dipartimento di Chimica "Giacomo Ciamician", Università di Bologna, via Selmi 2, 40126, Bologna, Italy.

Massimo Marcaccio (M)

Dipartimento di Chimica "Giacomo Ciamician", Università di Bologna, via Selmi 2, 40126, Bologna, Italy.

Stéphane Campidelli (S)

Université Paris-Saclay, CEA, CNRS, NIMBE, LICSEN, 91191, Gif-sur-Yvette, France.

Classifications MeSH