Selenophene-containing heterotriacenes by a C–Se coupling/cyclization reaction

• Pierre-Olivier Schwartz,
• Sebastian Förtsch,
• Astrid Vogt,
• Elena Mena-Osteritz and
• Peter Bäuerle

Beilstein J. Org. Chem. 2019, 15, 1379–1393, doi:10.3762/bjoc.15.138

• crucial cyclization steps to the stable and soluble fused systems were achieved by copper-catalyzed C–S and C–Se coupling/cyclization reactions. Structures and packing motifs in the solid state were elucidated by single crystal X-ray analysis and XRD powder measurements. Comparison of the optoelectronic

• properties provides interesting structure–property relationships and gives valuable insights into the role of heteroatoms within the series of the heterotriacenes. Electrooxidative polymerization led to the corresponding poly(heterotriacene)s P2–P4. Keywords: conducting polymer; C–S coupling; C–Se coupling

• preparation, efficient multistep synthesis routes with good overall yields based on recently published transition metal-catalyzed C–S and C–Se coupling/cyclization reactions in the crucial cyclization steps of iodinated bithiophene and biselenophene precursors. Heterotriacenes 1–4 turned out to be stable and