Straightforward Access to Multifunctional π-Conjugated P-Heterocycles Featuring an Internal Ylidic Bond.


Journal

Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543

Informations de publication

Date de publication:
01 Aug 2022
Historique:
received: 15 04 2022
pubmed: 4 6 2022
medline: 4 6 2022
entrez: 3 6 2022
Statut: ppublish

Résumé

We report the straightforward one-pot synthesis of novel 5- or 6-membered P-heterocycles featuring an internal ylidic bond: P-containing acenaphthylenes and phenanthrenes. The stability of the compounds tolerates post-functionalization through direct arylation to introduce electron-rich/poor substituents and the synthetic strategy is also compatible with the preparation of more elaborate polyaromatic scaffolds such as acenes and helicenes. Using a joint experimental (X-ray analysis, optical and redox properties) and theoretical approach, we perform a full structure-property relationships study on these new platforms. In particular, we show that molecular engineering allows not only tuning their absorption/emission across the entire visible range but also endowing them with chiroptical or non-linear optical properties, making them valuable dyes for a large panel of photonic or opto-electronic applications.

Identifiants

pubmed: 35657685
doi: 10.1002/anie.202205548
pmc: PMC9400969
doi:

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

e202205548

Subventions

Organisme : ANR
ID : ANR-16-CE05-0003-01

Informations de copyright

© 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.

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Auteurs

Thomas Delouche (T)

Univ Rennes, CNRS, ISCR-UMR 6226, ScanMAT-UMS 2001, 35000, Rennes, France.

Elsa Caytan (E)

Univ Rennes, CNRS, ISCR-UMR 6226, ScanMAT-UMS 2001, 35000, Rennes, France.

Marie Cordier (M)

Univ Rennes, CNRS, ISCR-UMR 6226, ScanMAT-UMS 2001, 35000, Rennes, France.

Thierry Roisnel (T)

Univ Rennes, CNRS, ISCR-UMR 6226, ScanMAT-UMS 2001, 35000, Rennes, France.

Grégory Taupier (G)

Univ Rennes, CNRS, ISCR-UMR 6226, ScanMAT-UMS 2001, 35000, Rennes, France.

Yann Molard (Y)

Univ Rennes, CNRS, ISCR-UMR 6226, ScanMAT-UMS 2001, 35000, Rennes, France.

Nicolas Vanthuyne (N)

Aix Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille, France.

Boris Le Guennic (B)

Univ Rennes, CNRS, ISCR-UMR 6226, ScanMAT-UMS 2001, 35000, Rennes, France.

Muriel Hissler (M)

Univ Rennes, CNRS, ISCR-UMR 6226, ScanMAT-UMS 2001, 35000, Rennes, France.

Denis Jacquemin (D)

CEISAM Lab-UMR 6230, CNRS, Nantes University, Nantes, France.

Pierre-Antoine Bouit (PA)

Univ Rennes, CNRS, ISCR-UMR 6226, ScanMAT-UMS 2001, 35000, Rennes, France.

Classifications MeSH