A Modular and Catalytic Methodology To Access 2,5-Furan-Based Phenylene/Thiophene Oligomers through a One-Pot Decarboxylative Cross-Coupling from 5‑Bromofurfural

A library of 2,5-furan-based phenylene/thiophene oligomers were synthesized starting from 5-bromofurfural, a derivative of biomass-derived furfural. Varied electronic groups are coupled onto the furan motif, followed by the installation of a phenylene or thiophene central linker through a one-pot Pd...

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Bibliographic Details
Published in:Journal of organic chemistry 2024-06, Vol.89 (11), p.8249-8254
Main Authors: Cigana, Brandon, Lapointe, Victoria, Majewski, Marek B., Forgione, Pat
Format: Article
Language:English
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Summary:A library of 2,5-furan-based phenylene/thiophene oligomers were synthesized starting from 5-bromofurfural, a derivative of biomass-derived furfural. Varied electronic groups are coupled onto the furan motif, followed by the installation of a phenylene or thiophene central linker through a one-pot Pd-catalyzed decarboxylative cross-coupling reaction. Resulting oligomers containing the furan-phenylene-furan core possess high photoluminescent quantum yields in solution (83–98%), which are crucial for optoelectronic devices. Absorbance and photoluminescence maxima are tuned by changing peripheral functional groups and the center linker coupled onto the furan backbone.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.4c00347