Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 42, Pages 12334-12338Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201502840
Keywords
amination; heteroacenes; nitrogensulfur heterocycles; structure-property relationships; X-ray structure analysis
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Funding
- Ministry for Education and Research (BMBF) [LOTsE 03K3505G]
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A new class of pi-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.
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