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2,7,11,16‐Tetra‐ tert ‐Butyl Tetraindenopyrene Revisited by an “Inverse” Synthetic Approach
Author(s) -
Elbert Sven M.,
Haidisch Anika,
Kirschbaum Tobias,
Rominger Frank,
Zschieschang Ute,
Klauk Hagen,
Mastalerz Michael
Publication year - 2020
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.202001555
Subject(s) - tetra , semiconductor , dispersion (optics) , palladium , thin film transistor , yield (engineering) , inverse , materials science , inversion (geology) , optoelectronics , catalysis , chemistry , nanotechnology , mathematics , optics , physics , medicinal chemistry , organic chemistry , composite material , geometry , layer (electronics) , paleontology , structural basin , biology
Abstract A new synthetic route to tetraindenopyrene (TIP)—a bowl‐shaped cut‐out structure of C 70 —is reported. The key step in this approach is a fourfold palladium‐catalyzed C−H activation that increases the yield more than 50 times in comparison to the approach originally described by Scott and co‐workers. Besides examination of its optoelectronic properties and study of its aggregation in solution, TIP was also re‐investigated by dispersion‐corrected DFT methods, which showed that dispersion interactions significantly increase the bowl‐to‐bowl inversion barrier. Furthermore, TIP was used as a semiconductor in p‐channel thin‐film transistors (TFTs).