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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.
A novel Friedel-Crafts-Bradsher reaction variant synthesizes dialkoxyphosphoryl substituted (hetero)acenes with high yields and excellent photoluminescence. This advancement accelerates the development of organic materials for optoelectronics.
Area of Science:
- Organic Chemistry
- Materials Science
- Photophysics
Background:
- Acenes are crucial organic semiconductors for optoelectronics.
- Developing efficient synthetic routes to functionalized acenes with tailored photophysical properties remains a challenge.
Purpose of the Study:
- To develop a new synthetic method for dialkoxyphosphoryl substituted (hetero)acenes.
- To investigate the impact of phosphonate substitution on the photophysical properties of acenes.
- To explore the potential of these compounds in optoelectronic applications.
Main Methods:
- A modified Friedel-Crafts-Bradsher reaction.
- Synthesis of tri- and tetracyclic (hetero)acenes.
- Photoluminescence quantum yield (PL QY) measurements.
- Density Functional Theory (DFT) and Time-Dependent DFT (TD-DFT) calculations.
- Electron-hole analysis.
Main Results:
- High chemical yields (up to 95%) achieved under mild, room temperature conditions.
- Excellent photoluminescence quantum yields (up to 87.7%) and large Stokes shifts (up to 7943 cm⁻¹).
- Phosphonate substitution significantly enhances PL QYs (more than twofold increase).
- DFT calculations suggest local excitation (LE) dominates, with charge transfer (CT) contributing to high fluorescence.
- Optimal properties observed for multiply substituted (hetero)acenes with fewer fused rings.
Conclusions:
- The new F-C-B reaction provides efficient access to valuable dialkoxyphosphoryl substituted (hetero)acenes.
- Phosphonate groups are effective in tuning photophysical properties, leading to enhanced PL QYs.
- These compounds show promise for optoelectronic applications due to their stability and high luminescence.
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