A Stable Hexaazaoctacene Cruciform σ-Dimer.

Adv Sci (Weinh)

Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.

Published: September 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 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 of > 5 d in dilute solution under ambient conditions. In the crystalline state it is persistent for > 10 months.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9507379PMC
http://dx.doi.org/10.1002/advs.202202710DOI Listing

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A Stable Hexaazaoctacene Cruciform σ-Dimer.

Adv Sci (Weinh)

September 2022

Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.

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 results in a 7,7'-bi(hexaazaoctacenyl). In addition to eight TIPS-ethynyl groups, the bioctacene motif protects the azaoctacene subunits.

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