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

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-decaazapen...

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Published in:Communications chemistry 2021-03, Vol.4 (1), p.29-29, Article 29
Main Authors: Miklík, David, Fatemeh Mousavi, S., Burešová, Zuzana, Middleton, Anna, Matsushita, Yoshitaka, Labuta, Jan, Ahsan, Aisha, Buimaga-Iarinca, Luiza, Karr, Paul A., Bureš, Filip, Richards, Gary J., Švec, Pavel, Mori, Toshiyuki, Ariga, Katsuhiko, Wakayama, Yutaka, Morari, Cristian, D’Souza, Francis, Jung, Thomas A., Hill, Jonathan P.
Format: Article
Language:English
Subjects:
639/638/542/970
639/925/357/341
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Chromophores
Electronic systems
Optical properties
Organic materials
Oxidation
Self-assembly
Substrates
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Summary: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. Acenes are a promising class of organic materials with distinctive electronic and optical properties. Here decaazapentacene and octaazatetracenes are prepared and their self-assembly behaviour at different oxidation states is analysed.
ISSN:2399-3669
2399-3669
DOI:10.1038/s42004-021-00470-w