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

• DOI: 10.1002/anie.201507104
• Publication Date: 2015-10-20T15:23:31Z
• Authors: Cameron Rogers; Chen Chen; Zahra Pedramrazi; Arash A. Omrani; Hsin‐Zon Tsai; Han Sae Jung; Song Lin; Michael F. Crommie; Felix R. Fischer
• Keywords: arenes; Chemical sciences; Organic Chemistry; Chemical Sciences; graphene; periacene; surface chemistry; 540; 01 natural sciences; non-contact AFM; 0104 chemical sciences

AbstractThe 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.