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

Authors: Cigana BLapointe VMajewski MBForgione P


Affiliations

1 Department of Chemistry and Biochemistry and Centre for Nanoscience Research (CeNSR), Concordia University, Montréal, QC H4B 1R6, Canada.
2 Centre for Green Chemistry and Catalysis, McGill University, Montréal, QC H3A 0B8, Canada.

Description

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.


Links

PubMed: https://pubmed.ncbi.nlm.nih.gov/38808994/

DOI: 10.1021/acs.joc.4c00347