A C 54 B 2 Polycyclic π-System with Bilayer Assembly and Multi-Redox Activity

Abstract

Open AccessCCS ChemistryRESEARCH ARTICLE21 Apr 2022A C54B2 Polycyclic π-System with Bilayer Assembly and Multi-Redox Activity Liuzhong Yuan, Jiaxiang Guo, Yue Yang, Kaiqi Ye, Chuandong Dou and Yue Wang Liuzhong Yuan Google Scholar More articles by this author , Jiaxiang Guo Google Scholar More articles by this author , Yue Yang Google Scholar More articles by this author , Kaiqi Ye Google Scholar More articles by this author , Chuandong Dou Google Scholar More articles by this author and Yue Wang Google Scholar More articles by this author https://doi.org/10.31635/ccschem.022.202201738 SectionsSupplemental MaterialAboutPDF ToolsAdd to favoritesDownload CitationsTrack Citations ShareFacebookTwitterLinked InEmail Doping heteroatoms into polycyclic aromatic hydrocarbons (PAHs) is an efficient strategy to achieve fascinating electronic structures and materials. However, nanoscale B-doped PAHs remain very challenging, because of the intrinsic instability of the boron atom and the lack of suitable precursors. In this study, we reported a C54B2 polycyclic π-system where one 1,4-diboron-substituted benzene subunit is embedded, which was successfully synthesized from doubly B-doped heptazethrene. This molecule represents not only the largest B-doped PAH by far but also an unprecedented B-doped nanographene. The fully zigzag-armchair edged structure creates its planar conformation, thus leading to the unique bilayer assembly behavior. More importantly, it possesses intriguing electronic structure and optoelectronic properties, such as very broad light absorption that covers 350–750 nm but sharp near-infrared fluorescence with a band width of only 26 nm, as well as reversible five-step redox capability, all of which are rarely observed for other B-doped PAHs. In addition, this molecule displays distinctive local aromaticity that cannot be reproduced via the reduction manipulation of all-carbon congener. Download figure Download PowerPoint Previous articleNext article FiguresReferencesRelatedDetails Issue AssignmentNot Yet AssignedSupporting Information Copyright & Permissions© 2022 Chinese Chemical Society Downloaded 184 times PDF DownloadLoading ...