scholarly journals Novel Synthetic Approach to Heteroatom Doped Polycyclic Aromatic Hydrocarbons: Optimizing the Bottom-Up Approach to Atomically Precise Doped Nanographenes

Molecules ◽  
2021 ◽  
Vol 26 (20) ◽  
pp. 6306
Author(s):  
Giacomo Biagiotti ◽  
Ilaria Perini ◽  
Barbara Richichi ◽  
Stefano Cicchi

The success of the rational bottom-up approach to nanostructured carbon materials and the discovery of the importance of their doping with heteroatoms puts under the spotlight all synthetic organic approaches to polycyclic aromatic hydrocarbons. The construction of atomically precise heteroatom doped nanographenes has evidenced the importance of controlling its geometry and the position of the doping heteroatoms, since these parameters influence their chemical–physical properties and their applications. The growing interest towards this research topic is testified by the large number of works published in this area, which have transformed a once “fundamental research” into applied research at the cutting edge of technology. This review analyzes the most recent synthetic approaches to this class of compounds.

Synlett ◽  
2019 ◽  
Vol 31 (03) ◽  
pp. 211-222
Author(s):  
Junzhi Liu ◽  
Xinliang Feng

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 Introduction2 Nitrogen-Doped PAHs Based on Dibenzo-9a-azaphenalene (DBAP)3 Cationic Nitrogen-Doped Helical PAHs4 Nitrogen–Boron–Nitrogen-Doped PAHs5 Conclusion and Outlook


2017 ◽  
Vol 53 (60) ◽  
pp. 8474-8477 ◽  
Author(s):  
Yulan Chen ◽  
Tomasz Marszalek ◽  
Torsten Fritz ◽  
Martin Baumgarten ◽  
Manfred Wagner ◽  
...  

Three tetrapyrene-fused benzocoronenes were synthesized by a “bottom-up” approach, which offers a facile access to extended polycyclic aromatic hydrocarbons with cove regions and zig-zag edges.


2021 ◽  
Vol 8 (1) ◽  
pp. 10-17
Author(s):  
Yannik Appiarius ◽  
Tim Stauch ◽  
Enno Lork ◽  
Pascal Rusch ◽  
Nadja C. Bigall ◽  
...  

A synthetic approach towards boron-nitrogen substituted polycyclic aromatic hydrocarbons (BN-PAHs) via electrophilic cyclization is described and it is shown that the variation of the rings' connectivity may tune the emission wavelengths effectively.


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