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Conjugated oligomers with alternating heterocycles from a single monomer: synthesis and demonstration of electroluminescence

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Abstract

Conjugated oligomers based on two different heterocycles are typically prepared by step growth polycondensation cross-coupling methods from two monomers X-Cycle1-X and M-Cycle2-M with no control of the regioselectivity. In this work, we used a new synthetic strategy that involves an extremely chemoselective reaction of a dielectrophilic compound, X1-Cycle1-X2, with a dinucleophilic component, M1-Cycle2-M2, under Stille conditions. The resulting monomers, X1-Cycle1-Cycle2-M2 are di-heterocyclic push–pull monomers that still contain a nucleophilic site (boronic acid) and electrophilic site (bromide) and are set up for a controlled polymerization under Suzuki conditions. In this way, two semiconducting oligomers, based on thiophene/benzene and thiophene/pyridine motifs were synthesized. Both oligomers were characterized in terms of their thermal, electrochemical, absorption, emission and electroluminescence properties.

Graphical abstract: Conjugated oligomers with alternating heterocycles from a single monomer: synthesis and demonstration of electroluminescence

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Publication details

The article was received on 27 Jul 2019, accepted on 13 Sep 2019 and first published on 17 Sep 2019


Article type: Research Article
DOI: 10.1039/C9QO00947G
Org. Chem. Front., 2019, Advance Article

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    Conjugated oligomers with alternating heterocycles from a single monomer: synthesis and demonstration of electroluminescence

    S. Urrego-Riveros, M. Bremer, J. Hoffmann, A. Heitmann, T. Reynaldo, J. Buhl, P. J. Gates, F. D. Sönnichsen, M. Hissler, M. Gerken and A. Staubitz, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO00947G

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