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Syntheses and Physical Properties of Cationic BN‐Embedded Polycyclic Aromatic Hydrocarbons
Author(s) -
Gotoh Hajime,
Nakatsuka Soichiro,
Tanaka Hiroki,
Yasuda Nobuhiro,
Haketa Yohei,
Maeda Hiromitsu,
Hatakeyama Takuji
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202103488
Subject(s) - hypsochromic shift , chemistry , cationic polymerization , homo/lumo , polycyclic aromatic hydrocarbon , ion , pyridine , photochemistry , medicinal chemistry , organic chemistry , molecule , physics , quantum mechanics , fluorescence
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.