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

Sara Urrego-Riveros; Matthias Bremer; Jonas Hoffmann; Anne Heitmann; Thibault Reynaldo; Janek Buhl; Paul J. Gates; Frank D. Sönnichsen; Muriel Hissler; Martina Gerken; Anne Staubitz

doi:10.1039/C9QO00947G

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

Sara Urrego-Riveros,

^abc Matthias Bremer,^d Jonas Hoffmann,

^abe Anne Heitmann,^ab Thibault Reynaldo,^e Janek Buhl,^d Paul J. Gates,

^f Frank D. Sönnichsen,

^c Muriel Hissler,

^e Martina Gerken

^d and Anne Staubitz

*^abc

Author affiliations

* Corresponding authors

^a Institute for Organic and Analytical Chemistry, University of Bremen, Leobener Str.7 NW2C, 28359 Bremen, Germany
E-mail: Staubitz@uni-bremen.de

^b University of Bremen, MAPEX Center for Materials and Processes, Bibliothekstr. 1, 28359 Bremen, Germany

^c Otto-Diels-Institute for Organic Chemistry, University of Kiel, Otto-Hahn-Platz 4, 24098 Kiel, Germany

^d Institute of Electrical Engineering and Information Technology, University of Kiel, Kaiserstr.2, 24143 Kiel, Germany

^e Univ Rennes, CNRS, ISCR – UMR 6226, F-35000 Rennes, France

^f School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, UK

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.

Organic Chemistry Frontiers

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

Abstract

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

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