Pyrazinacenes exhibit on-surface oxidation-state-dependent conformational and self-assembly behaviours

David Miklík, S. Fatemeh Mousavi, Zuzana Burešová, Anna Middleton, Yoshitaka Matsushita, Jan Labuta, Aisha Ahsan, Luiza Buimaga-Iarinca, Paul A. Karr, Filip Bureš, Gary J. Richards, Pavel Švec, Toshiyuki Mori, Katsuhiko Ariga, Yutaka Wakayama, Cristian Morari, Francis D’Souza, Thomas A. Jung, Jonathan P. Hill

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)


Acenes and azaacenes lie at the core of molecular materials’ applications due to their important optical and electronic features. A critical aspect is provided by their heteroatom multiplicity, which can strongly affect their properties. Here we report pyrazinacenes containing the dihydro-decaazapentacene and dihydro-octaazatetracene chromophores and compare their properties/functions as a model case at an oxidizing metal substrate. We find a distinguished, oxidation-state-dependent conformational adaptation and self-assembly behaviour and discuss the analogies and differences of planar benzo-substituted decaazapentacene and octaazatetracene forms. Our broad experimental and theoretical study reveals that decaazapentacene is stable against oxidation but unstable against reduction, which is in contrast to pentacene, its C–H only analogue. Decaazapentacenes studied here combine a planar molecular backbone with conformationally flexible substituents. They provide a rich model case to understand the properties of a redox-switchable π-electronic system in solution and at interfaces. Pyrazinacenes represent an unusual class of redox-active chromophores.

Original languageEnglish
Article number29
JournalCommunications Chemistry
Issue number1
Publication statusPublished - 2021 Dec

ASJC Scopus subject areas

  • Biochemistry
  • Chemistry(all)
  • Environmental Chemistry
  • Materials Chemistry


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