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: Heckershoff, Robin (Author) , Maier, Steffen (Author) , Wurm, Thomas (Author) , Biegger, Philipp (Author) , Brödner, Kerstin (Author) , Krämer, Petra (Author) , Hoffmann, Marvin (Author) , Eberle, Lukas (Author) , Stein, Jana (Author) , Rominger, Frank (Author) , Rudolph, Matthias (Author) , Freudenberg, Jan (Author) , Dreuw, Andreas (Author) , Hashmi, A. Stephen K. (Author) , Bunz, Uwe H. F. (Author)
Format: Article (Journal)
Language:English
Published: February 24, 2022
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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Summary: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.
Item Description:Online veröffentlicht am 12. Januar 2022
Gesehen am 15.12.2022
Physical Description:Online Resource
ISSN:1521-3765
DOI:10.1002/chem.202104203