Bottom-Up Synthesis of Nitrogen-Doped Polycyclic Aromatic Hydrocarbons

Abstract Bottom-up organic synthesis serves as an efficient method to provide atomically precise heteroatom-doped polycyclic aromatic hydrocarbons (PAHs) with not only well-defined size and edge structures but also specific concentrations and positions of the heteroatoms. We provide a plenary accoun...

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Bibliographic Details
Published in:Synlett 2020-02, Vol.31 (3), p.211-222
Main Authors: Liu, Junzhi, Feng, Xinliang
Format: Article
Language:English
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Summary:Abstract Bottom-up organic synthesis serves as an efficient method to provide atomically precise heteroatom-doped polycyclic aromatic hydrocarbons (PAHs) with not only well-defined size and edge structures but also specific concentrations and positions of the heteroatoms. We provide a plenary account of the preparation of nitrogen-doped PAHs (N-PAHs) through 1,3-dipolar cycloaddition between different dipolarophiles, as well as pyrazine-type N-doped diaza-hexa-peri-hexabenzocoronene (diaza-HBC). Additionally, we present the synthesis of a class of helical N-charged PAHs, including one charged aza[5]helicene and two charged aza[4]helicenes. Moreover, the bottom-up organic synthesis strategy is further extended to the construction of novel nitrogen-boron-nitrogen (NBN)-containing PAHs. Finally, we discuss the synthesis of four-coordinate boron chromophores containing 6,12,18-tris(alkyl amine)-5,11,17-triazatrinaphthylene derivative ligands. 1 Introduction 2 Nitrogen-Doped PAHs Based on Dibenzo-9a-azaphenalene (DBAP) 3 Cationic Nitrogen-Doped Helical PAHs 4 Nitrogen–Boron–Nitrogen-Doped PAHs 5 Conclusion and Outlook
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0039-1690767