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A Stable Hexaazaoctacene Cruciform σ-Dimer
Steffen Maier1, Fabian Jester1, Marvin T Hoffmann2,3
1Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
Abstract:
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 MnO2 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 τ1/2 of > 5 d in dilute solution under ambient conditions. In the crystalline state it is persistent for > 10 months.
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