Substituted Cyclopentannulated Tetraazapentacenes. Issue 64 (19th September 2022)

• Record Type: Journal Article
• Authors: Maier, Steffen; Heckershoff, Robin; Hippchen, Nikolai; Brödner, Kerstin; Rominger, Frank; Freudenberg, Jan; Hashmi, A. Stephen K.; Bunz, Uwe H. F.
• Is Part Of: Chemistry. Volume 28:Issue 64(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-09-19
• Subjects: cyclization -- dihydroazaacenes -- postfunctionalization -- semiconductors -- solid-state packing; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202201842
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Brominated pentannulated dihydrotetraazapentacenes were prepared by gold‐ or palladium‐catalyzed 5‐ endo ‐ dig cyclization of TIPS‐ethynylated dihydrotetraazaacenes (TIPS = tri iso propylsilyl). Post‐functionalization was demonstrated by Sonogashira alkynylation and Rosenmund‐von Braun cyanation. Calculations predict these species to act as n‐type semiconductors, which was verified for two derivates through characterization in organic field‐effect transistors. Abstract : The introduction of bromine substituents into cyclopentannulated tetraazapentacenes allows post‐functionalization, for example through Sonogashira coupling and Rosenmund‐von Braun reaction. The altered properties of the resulting new compounds were examined by experimental and computational methods, and the potential use as organic field‐effect transistors was demonstrated.