Tropo(thio)ne-embedded homoHPHACs: does the tropylium cation induce global antiaromaticity in expanded hexapyrrolohexaazacoronene?

Masayoshi Takase; Atsushi Ueno; Kosuke Oki; Hiroki Matsumoto; Shigeki Mori; Tetsuo Okujima; Hidemitsu Uno

doi:10.1039/d1cc07152a

Tropo(thio)ne-embedded homoHPHACs: does the tropylium cation induce global antiaromaticity in expanded hexapyrrolohexaazacoronene?

Chem Commun (Camb). 2022 Mar 8;58(20):3366-3369. doi: 10.1039/d1cc07152a.

Authors

Masayoshi Takase¹, Atsushi Ueno¹, Kosuke Oki¹, Hiroki Matsumoto¹, Shigeki Mori², Tetsuo Okujima¹, Hidemitsu Uno¹

Affiliations

¹ Graduate School of Science and Engineering, Ehime University, Matsuyama 790-8577, Japan. takase.masayoshi.ry@ehime-u.ac.jp.
² Advanced Research Support Center, Ehime University, Matsuyama 790-8577, Japan.

PMID: 35188504
DOI: 10.1039/d1cc07152a

Abstract

Tropo(thio)ne-embedded homoHPHACs and their dications were synthesised by an electrophilic annulation of secoHPHAC and successive oxidation. ¹³C NMR spectra of the dications represented global 22π homoaromaticity via homoconjugation, while alkylation of a thiocarbonyl-bridged homoHPHAC produced a 24π antiaromatic monocation.