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Substituted Cyclopentannulated Tetraazapentacenes |
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| Authors: | Steffen Maier Robin Heckershoff Nikolai Hippchen Kerstin Brödner Dr Frank Rominger Dr Jan Freudenberg Prof A Stephen K Hashmi Prof Uwe H F Bunz |
| Institution: | 1. Organisch-Chemisches Institut (OCI), Heidelberg University, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
These authors contributed equally to this work.;2. Organisch-Chemisches Institut (OCI), Heidelberg University, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany |
| Abstract: | Brominated pentannulated dihydrotetraazapentacenes were prepared by gold- or palladium-catalyzed 5-endo-dig cyclization of TIPS-ethynylated dihydrotetraazaacenes (TIPS = triisopropylsilyl). Post-functionalization was demonstrated by Sonogashira alkynylation and Rosenmund-von Braun cyanation. Calculations predict these species to act as n-type semiconductors, which was verified for two derivates through characterization in organic field-effect transistors. |
| Keywords: | cyclization dihydroazaacenes postfunctionalization semiconductors solid-state packing |