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Cyclopentannulated Dihydrotetraazapentacenes
Author(s) -
Heckershoff Robin,
Maier Steffen,
Wurm Thomas,
Biegger Philipp,
Brödner Kerstin,
Krämer Petra,
Hoffmann Marvin T.,
Eberle Lukas,
Stein Jana,
Rominger Frank,
Rudolph Matthias,
Freudenberg Jan,
Dreuw Andreas,
Hashmi A. Stephen K.,
Bunz Uwe H. F.
Publication year - 2022
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202104203
Subject(s) - silylation , catalysis , selectivity , quantum chemical , transition metal , chemistry , crystallography , stereochemistry , medicinal chemistry , materials science , molecule , organic chemistry
The transition‐metal‐catalyzed cyclization of bissilylethynylated N , N ’‐dihydrotetraazapentacene (TIPS‐TAP‐H 2 ) 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.