Phosphine→Borane‐Functionalized Pyrenes and Anthracenes

The functionalization of polycyclic aromatic hydrocarbons (PAHs) with N→B Lewis pairs, so-called borylative fusion, has recently emerged as a simple and powerful means to modulate their electronic and photophysical properties thanks to the extension of the π system. Herein, we considered a new class of PAHs appended with phosphine→borane Lewis pairs and investigated pyrene as well as anthracene derivatives. In these compounds, strong P→B interactions are enforced geometrically, but the π-system is not extended. Nevertheless, such P→B functionalization was found to significantly impact the optical and electrochemical properties. The P,B-functionalized PAHs display noticeably reduced HOMO-LUMO gaps and enhanced fluorescence. Both the number and position of P→B units turned out to play a significant role.

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Publication Details

Journal
Angewandte Chemie International Edition
Published
2025-03-11
DOI
https://doi.org/10.1002/anie.202501178
Citations
6
Primary Topic
Asymmetric Hydrogenation and Catalysis
Type
article
Field-Weighted Citation Impact
3.22

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article

Phosphine→Borane‐Functionalized Pyrenes and Anthracenes

Karinne Miqueu, Jean‐Cyrille Hierso, Sonia Mallet‐Ladeira, Arnaud Le Gac et al.
6 citations
Angewandte Chemie International Edition
Asymmetric Hydrogenation and Catalysis
3.22
article

Phosphine→Borane‐Functionalized Pyrenes and Anthracenes

Karinne Miqueu, Jean‐Cyrille Hierso, Sonia Mallet‐Ladeira, Arnaud Le Gac, Julien Roger, Didier Bourissou, Ghenwa Bouhadir
article en
6 citations

Abstract

The functionalization of polycyclic aromatic hydrocarbons (PAHs) with N→B Lewis pairs, so-called borylative fusion, has recently emerged as a simple and powerful means to modulate their electronic and photophysical properties thanks to the extension of the π system. Herein, we considered a new class of PAHs appended with phosphine→borane Lewis pairs and investigated pyrene as well as anthracene derivatives. In these compounds, strong P→B interactions are enforced geometrically, but the π-system is not extended. Nevertheless, such P→B functionalization was found to significantly impact the optical and electrochemical properties. The P,B-functionalized PAHs display noticeably reduced HOMO-LUMO gaps and enhanced fluorescence. Both the number and position of P→B units turned out to play a significant role.

Angewandte Chemie International EditionVol. 64(19)
Centre National de la Recherche Scientifique (FR), Université Toulouse III - Paul Sabatier (FR), Université de Pau et des Pays de l'Adour (FR), Université de Bourgogne (FR), Université Fédérale de Toulouse Midi-Pyrénées (FR), Institut National Polytechnique de Toulouse (FR), Institut des Sciences Analytiques et de Physico-Chimie pour l'Environnement et les Matériaux (FR), Laboratoire de Chimie de Coordination (FR), Laboratoire Hétérochimie Fondamentale et Appliquée (FR), Université Bourgogne Europe (FR)
Agence Nationale de la Recherche, Centre National de la Recherche Scientifique, Grand Équipement National De Calcul Intensif, Région Occitanie Pyrénées-Méditerranée, Université de Pau et des Pays de l'Adour
Openalex Percentile: Top 8%
Asymmetric Hydrogenation and Catalysis
3.22
DOIOpen Access PDFOpenAlex
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