Syntheses and Physical Properties of Cationic BN‐Embedded Polycyclic Aromatic Hydrocarbons
Hajime Gotoh, Soichiro Nakatsuka, Hiroki Tanaka, Nobuhiro Yasuda, Yohei Haketa, Hiromitsu Maeda, Takuji Hatakeyama
Abstract
Abstract Cationic 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 + [BBr 4 − ] ) 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.