Syntheses and Physical Properties of Cationic BN‐Embedded Polycyclic Aromatic Hydrocarbons

• DOI: 10.1002/ange.202103488
• Publication Date: 2021-03-22T13:29:42Z
• Authors: Hajime Gotoh; Soichiro Nakatsuka; Hiroki Tanaka; Nobuhiro Yasuda; Yohei Haketa; Hiromitsu Maeda; Takuji Hatakeyama
• Keywords: 11. Sustainability; 01 natural sciences; 0104 chemical sciences

AbstractCationic BN‐embedded polycyclic aromatic hydrocarbons (BN‐PAH+s) were synthesized from a nitrogen‐containing macrocycle via pyridine‐directed tandem C−H borylation. Incorporating BN into PAH+resulted in a remarkable hypsochromic shift due to an increase in the LUMO energy and the symmetry changes of the HOMO and LUMO. Electrophilic substitution or anion exchange of BN‐PAH+possessing tetrabromoborate as a counter anion (BN+[BBr4−]) afforded air‐stable BN‐PAH/PAH+s. Of these,BN+[TfO−]allowed reversible two‐electron reduction and the formation of two‐dimensional brickwork‐type π‐electronic ion pair with 1,2,3,4,5‐pentacyanocyclopentadienyl anion, demonstrating the potential application of BN‐PAH+as electronic materials.