Cyclopentannulated dihydrotetraazapentacenes
The transition-metal-catalyzed cyclization of bissilylethynylated N,N’-dihydrotetraazapentacene (TIPS-TAP-H2) into bissilylated cyclopenta[fg,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...
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| Main Authors: | , , , , , , , , , , , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
February 24, 2022
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| In: |
Chemistry - a European journal
Year: 2022, Volume: 28, Issue: 12, Pages: 1-8 |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.202104203 |
| Online Access: | Verlag, kostenfrei, Volltext: https://doi.org/10.1002/chem.202104203 Verlag, kostenfrei, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.202104203 
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| Author Notes: | Robin Heckershoff, Steffen Maier, Thomas Wurm, Philipp Biegger, Kerstin Brödner, Petra Krämer, Marvin T. Hoffmann, Lukas Eberle, Jana Stein, Frank Rominger, Matthias Rudolph, Jan Freudenberg, Andreas Dreuw, A. Stephen K. Hashmi, and Uwe H.F. Bunz |
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| 520 | |a The transition-metal-catalyzed cyclization of bissilylethynylated N,N’-dihydrotetraazapentacene (TIPS-TAP-H2) into bissilylated cyclopenta[fg,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. | ||
| 650 | 4 | |a aromaticity | |
| 650 | 4 | |a azaarenes | |
| 650 | 4 | |a catalysis | |
| 650 | 4 | |a cycloisomerization | |
| 650 | 4 | |a cyclopentannulation | |
| 650 | 4 | |a silyl shift | |
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