Bottom-Up Synthesis of Nitrogen-Doped Polycyclic Aromatic Hydrocarbons,Synlett

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Bottom-Up Synthesis of Nitrogen-Doped Polycyclic Aromatic Hydrocarbons
Synlett ( IF 1.7 ) Pub Date : 2019-12-10 , DOI: 10.1055/s-0039-1690767
Junzhi Liu _{1,

2} , Xinliang Feng ₂

Affiliation

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

中文翻译：

自下而上合成掺氮多环芳烃

自下而上的有机合成是提供原子级精确的杂原子掺杂多环芳烃 (PAH) 的有效方法，不仅具有明确的尺寸和边缘结构，而且还具有特定的杂原子浓度和位置。我们提供了通过不同亲偶极体之间的 1,3-偶极环加成以及吡嗪型 N 掺杂二氮杂六环六苯并芴烯 (diaza-HBC) 制备氮掺杂多环芳烃 (N-PAHs) 的全体会议. 此外，我们展示了一类带 N 电荷的螺旋多环芳烃的合成，包括一个带电的氮杂[5]螺旋烯和两个带电的氮杂[4]螺旋烯。此外，自下而上的有机合成策略进一步扩展到新型含氮硼氮（NBN）多环芳烃的构建。最后，我们讨论了含有 6,12,18-三（烷基胺）-5,11,17-三氮杂三亚萘衍生物配体的四配位硼发色团的合成。1 引言 2 基于二苯并 9a-氮杂菲那烯 (DBAP) 的掺氮 PAH 3 阳离子掺氮螺旋 PAH 4 掺氮硼氮多环芳烃 5 结论与展望

更新日期：2019-12-10

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