A Stable Hexaazaoctacene Cruciform σ-Dimer.

Steffen MaierFabian JesterMarvin T HoffmannFrank RomingerJan FreudenbergAndreas DreuwUwe H F Bunz

Published in: Advanced science (Weinheim, Baden-Wurttemberg, Germany) (2022)

Buchwald-Hartwig coupling of a triisopropylsilyl (TIPS)-ethynylated dibromo-N,N'-dihydrotetraazapentacene with 1,4-bis(TIPS-ethynyl)-2,3-diaminonaphthalene furnishes a dihydrohexaazaoctacene. Its oxidation with MnO 2 results in a 7,7'-bi(hexaazaoctacenyl). In addition to eight TIPS-ethynyl groups, the bioctacene motif protects the azaoctacene subunits. The biazaoctacenyl displays a τ 1/2 of > 5 d in dilute solution under ambient conditions. In the crystalline state it is persistent for > 10 months.

Keyphrases

room temperature
air pollution
particulate matter
ionic liquid
hydrogen peroxide
electron transfer