Phosphine→Borane-Functionalized Pyrenes and Anthracenes.

Angew Chem Int Ed Engl

Laboratoire Hetérochimie Fondamentale et Appliquée (LHFA, UMR 5069), CNRS/Université Paul Sabatier, 118 Route de Narbonne, Toulouse, 31062 CEDEX 09, France.

Published: May 2025


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Article 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.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC12051744PMC
http://dx.doi.org/10.1002/anie.202501178DOI Listing

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