title: Fused thiophene-pyrrole-containing ring systems up to a heterodecacene.
abstract: A new class of π-conjugated polycyclic hydrocarbons that promises interesting electronic properties is presented. The synthesis and extension of the S,N-heteroacene series consisting of only five-membered heterocyclic rings up to a very long, stable, and still soluble decacene SN10 is realized by multiple Pd-catalyzed aminations of halogenated thiophene precursors as key reactions. These novel heteroacenes were characterized by optical spectroscopy and electrochemistry providing interesting structure-property relationships. Nearly complete bond-length equalization in the inner part of the conjugated backbone and an unusual herringbone packing in the solid state underline the structural features of these novel systems.
authors.affiliation: Institute of Organic Chemistry II and Advanced Materials, University of Ulm, Albert-Einstein-Allee 11, 89081 Ulm (Germany) http://www.uni-ulm.de/nawi/nawi-oc2/
authors.forename: Christoph
authors.initials: C
authors.lastname: Wetzel
authors.affiliation: Institute of Organic Chemistry II and Advanced Materials, University of Ulm, Albert-Einstein-Allee 11, 89081 Ulm (Germany) http://www.uni-ulm.de/nawi/nawi-oc2/
authors.forename: Eduard
authors.initials: E
authors.lastname: Brier
authors.affiliation: Institute of Organic Chemistry II and Advanced Materials, University of Ulm, Albert-Einstein-Allee 11, 89081 Ulm (Germany) http://www.uni-ulm.de/nawi/nawi-oc2/
authors.forename: Astrid
authors.initials: A
authors.lastname: Vogt
authors.affiliation: Institute of Organic Chemistry II and Advanced Materials, University of Ulm, Albert-Einstein-Allee 11, 89081 Ulm (Germany) http://www.uni-ulm.de/nawi/nawi-oc2/
authors.forename: Amaresh
authors.initials: A
authors.lastname: Mishra
authors.affiliation: Institute of Organic Chemistry II and Advanced Materials, University of Ulm, Albert-Einstein-Allee 11, 89081 Ulm (Germany) http://www.uni-ulm.de/nawi/nawi-oc2/
authors.forename: Elena
authors.initials: E
authors.lastname: Mena-Osteritz
authors.affiliation: Institute of Organic Chemistry II and Advanced Materials, University of Ulm, Albert-Einstein-Allee 11, 89081 Ulm (Germany) http://www.uni-ulm.de/nawi/nawi-oc2/. peter.baeuerle@uni-ulm.de.
authors.forename: Peter
authors.initials: P
authors.lastname: Bäuerle
keywords: X-ray structure analysis; amination; heteroacenes; nitrogen-sulfur heterocycles; structure-property relationships