Bottom-Up Synthesis of Nitrogen-Doped Polycyclic Aromatic Hydrocarbons

Research output: Contribution to journalResearch articleContributedpeer-review


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.


Original languageEnglish
Pages (from-to)211-222
Number of pages12
Issue number3
Publication statusPublished - 2020


ASJC Scopus subject areas


  • boron doping, heteroatoms, nanographenes, nitrogen doping, polycyclic aromatic hydrocarbons