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Synthesis and Reactivity of Dithienopyrazines** |
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| Authors: | Dr. Franziska Kreuzer Anna Aubele Dr. Elena Mena-Osteritz Prof. Dr. Peter Bäuerle |
| Affiliation: | 1. Institute of Organic Chemistry II and Advanced Materials, University of Ulm, Albert-Einstein-Allee 11, 89081 Ulm, Germany Mattson Thermal Products GmbH, 89160 Dornstadt, Germany Contribution: Investigation (lead);2. Institute of Organic Chemistry II and Advanced Materials, University of Ulm, Albert-Einstein-Allee 11, 89081 Ulm, Germany Contribution: Visualization (supporting);3. Institute of Organic Chemistry II and Advanced Materials, University of Ulm, Albert-Einstein-Allee 11, 89081 Ulm, Germany |
| Abstract: | Heteroacenes developed to widely used building blocks in organic semiconductors for application in organic electronics due to their tunable structures and properties concomitant with inherent stability. Here, we report efficient preparation and investigation of so far unknown heterotriacenes, basic anti- and syn-dithienopyrazine 5 and 6 . The comparison of the two isomers with respect to electronic properties and follow-up reactions gives insights into structure-property and -reactivity relationships. Examples of transition metal-catalyzed C−C cross-coupling reactions of corresponding halogenated derivatives show the practical impact for extended π-conjugated systems applied in optoelectronic devices. |
| Keywords: | C−C coupling reaction dithienopyrazine electrophilic halogenation lithiation X-ray structure analysis |