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Photostable π-Expanded Furans via Base-Mediated Quinone Oxygen-Annulation
Abhishek Pareek1, Maja Morawiak1, Emran Masoumifeshani1
1Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.
The Journal of Organic Chemistry
|February 10, 2026
Summary
Researchers developed a new method to create stable, fluorescent π-expanded furans from chloroquinones and aromatic alcohols. These novel chromophores exhibit excellent photostability, outperforming existing materials under UV irradiation.
Area of Science:
- Organic Chemistry
- Materials Science
- Photochemistry
Background:
- Developing novel chromophores with enhanced photostability is crucial for advanced optical and electronic applications.
- Existing fluorescent materials often suffer from photodegradation, limiting their long-term performance.
Purpose of the Study:
- To synthesize novel π-expanded furans with high yields and excellent photostability.
- To investigate the photophysical properties and electronic transitions of the synthesized compounds.
- To explore their potential as stable fluorescent materials.
Main Methods:
- One-pot oxygen-annulation reaction between chloroquinones and aromatic alcohols.
- Triisopropylsilyl (TIPS)-acetylene functionalization for solubility enhancement.
- Reductive aromatization to form stable chromophores.
- Time-dependent density functional theory (TD-DFT) for electronic structure analysis.
Main Results:
- Efficient synthesis of π-expanded furans with yields up to 91%.
- Obtained chromophores exhibit blue absorption and strong fluorescence.
- TD-DFT revealed distinct excitation mechanisms in intermediates versus final products.
- Demonstrated superior UV photostability compared to TIPS-pentacene.
Conclusions:
- The developed one-pot method provides access to highly photostable π-expanded furans.
- These novel chromophores possess promising properties for applications requiring long-term light exposure.
- The study offers insights into structure-property relationships for fluorescent organic materials.
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