A Stable Hexaazaoctacene Cruciform σ-Dimer

Steffen Maier; Fabian Jester; Marvin T Hoffmann; Frank Rominger; Jan Freudenberg; Andreas Dreuw; Uwe H F Bunz

doi:10.1002/advs.202202710

A Stable Hexaazaoctacene Cruciform σ-Dimer

Adv Sci (Weinh). 2022 Sep;9(27):e2202710. doi: 10.1002/advs.202202710. Epub 2022 Jul 27.

Authors

Steffen Maier¹, Fabian Jester¹, Marvin T Hoffmann^{2

3}, Frank Rominger¹, Jan Freudenberg¹, Andreas Dreuw^{2

3}, Uwe H F Bunz^{1

4}

Affiliations

¹ Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
² Interdisziplinäres Zentrum für Wissenschaftliches Rechnen, Universität Heidelberg, Im Neuenheimer Feld 205A, 69120, Heidelberg, Germany.
³ Physikalisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 253, 69120, Heidelberg, Germany.
⁴ Centre for Advanced Materials (CAM), Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 225, 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 τ_1/2 of > 5 d in dilute solution under ambient conditions. In the crystalline state it is persistent for > 10 months.

Keywords: acenes; azaoctacene; biacenyl; heteroacene; octacene; stabilization.

Grants and funding

SFB 1249/DFG