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Cyclopentannulated Dihydrotetraazapentacenes |
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| Authors: | Robin Heckershoff Steffen Maier Dr Thomas Wurm Dr Philipp Biegger Kerstin Brödner Petra Krämer Dr Marvin T Hoffmann Lukas Eberle Jana Stein Dr Frank Rominger Dr Matthias Rudolph Dr Jan Freudenberg Prof Andreas Dreuw Prof A Stephen K Hashmi Prof Uwe H F Bunz |
| Institution: | 1. Organisch-Chemisches Institut (OCI), Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
These authors contributed equally to this work.;2. Organisch-Chemisches Institut (OCI), Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany;3. Interdisziplinäres Zentrum für Wissenschaftliches Rechnen (IWR), Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 205 A, 69120 Heidelberg, Germany |
| Abstract: | The transition-metal-catalyzed cyclization of bissilylethynylated N,N’-dihydrotetraazapentacene (TIPS-TAP-H2) into bissilylated cyclopentafg,qr]pentacenes is reported. Depending on the catalyst either none, one or two silyl groups migrate and change their positions in the formed five-membered rings. The optoelectronic properties are quite similar, whereas the packing motifs differ dramatically. Control experiments and quantum chemical calculations were performed to investigate the mechanism of the reaction and the selectivity of the silyl shift. |
| Keywords: | aromaticity azaarenes catalysis cyclopentannulation cycloisomerization silyl shift |