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Updated: Sep 20, 2025

Low-energy Cathodoluminescence for OxyNitride Phosphors
Published on: November 15, 2016
Multiply Substituted (Hetero)acenes Containing Phosphonate Group at the Central Unit as High-Efficiency Light
Marek Koprowski1, Łucja Knopik1,2, Ewa Różycka-Sokołowska3
1Division of Organic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, Łódź, 90-363, Poland.
Abstract:
A new variant of the Friedel-Crafts-Bradsher (F-C-B) reaction offers access to dialkoxyphosphoryl substituted (hetero)acenes, especially to previously unavailable three- to seven-substituted, tri- and tetracyclic compounds, and features high chemical yields up to 95%, excellent photoluminescence (PL) quantum yields (QYs) up to 87.7%, large Stokes shifts up to 7943 cm-1, and very mild, room temperature reaction conditions. The (RO)2P(O) has a distinct effect on the photophysical properties of acenes, increasing QYs by more than twofold compared to identical acenes not substituted by this group. DFT and TD-DFT calculations, combined with electron-hole analysis, indicated that local excitation (LE) had the dominant contribution to the electron excitation mechanism, and charge transfer (CT) of about 30% provided the highest fluorescence QYs. The multiple substitutions of (hetero)acenes bearing phosphonate moieties and electron-diverse substituents combined with a lower number of fused aromatic rings appear to be ideal for optimal chemical stability and high PL. The new, synthetic tool will accelerate exploitation of bulky (hetero)acene emitters for optoelectronic applications.
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