Closing the Nanographene Gap: Surface-Assisted Synthesis of Peripentacene from 6,6′-Bipentacene Precursors

• Published in: Angewandte Chemie 2015-12, Vol.127 (50), p.15358-15361
• Main Authors: Rogers, Cameron, Chen, Chen, Pedramrazi, Zahra, Omrani, Arash A., Tsai, Hsin-Zon, Jung, Han Sae, Lin, Song, Crommie, Michael F., Fischer, Felix R.
• Format: Article
• Language: eng ; ger
• Subjects: Arene; Chairs; Chemistry; Electronics; Graphen; Kontaktfreie AFM; Magnetic devices; Nanostructure; Oberflächenchemie; Pentacene; Periacen; Polycyclic aromatic hydrocarbons; Precursors; Strategy; Synthesis
• ISSN: 0044-8249; 1521-3757
• DOI: 10.1002/ange.201507104

The thermally induced cyclodehydrogenation reaction of 6,6′‐bipentacene precursors on Au(111) yields peripentacene stabilized by surface interactions with the underlying metallic substrate. STM and atomic‐resolution non‐contact AFM imaging reveal rectangular flakes of nanographene featuring parallel pairs of zig‐zag and armchair edges resulting from the lateral fusion of two pentacene subunits. The synthesis of a novel molecular precursor 6,6′‐bipentacene, itself a synthetic target of interest for optical and electronic applications, is also reported. The scalable synthetic strategy promises to afford access to a structurally diverse class of extended periacenes and related polycyclic aromatic hydrocarbons as advanced materials for electronic, spintronic, optical, and magnetic devices. Ein oberflächenstabilisiertes Peripentacen wurde synthetisiert und durch kontaktfreie AFM‐Bildgebung mit atomarer Auflösung visualisiert. Das Schlüsselintermediat ist die metastabile 6,6‐Bipentacen‐Vorstufe, die durch eine Diazo‐Thioketon‐Kupplung und anschließende selektive 1,4‐Eliminierung erhalten wurde.