2, 7, 11, 16‐Tetra‐tert‐Butyl Tetraindenopyrene Revisited by an "Inverse" Synthetic Approach. Issue 46 (20th July 2020)

• Record Type: Journal Article
• Authors: Elbert, Sven M.; Haidisch, Anika; Kirschbaum, Tobias; Rominger, Frank; Zschieschang, Ute; Klauk, Hagen; Mastalerz, Michael
• Is Part Of: Chemistry. Volume 26:Issue 46(2020)
• Page Start: 10585
• Page End: 10590
• Publication Date: 2020-07-20
• Subjects: C−H activation -- organic thin film transistors -- polycyclic aromatic hydrocarbons -- pyrene -- tetraindenopyrene; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202001555
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: A new synthetic route to tetraindenopyrene (TIP)—a bowl‐shaped cut‐out structure of C70 —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). Abstract : Bowled over : An "inverse" route to a tetraindenopyrene (TIP), which is a cut‐out structure of C70, is presented. The compound was reinvestigated by DFT calculations and tested as a semiconductor in p‐channel organic thin‐film transistors.