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

Miklík, David and Mousavi, S. Fatemeh and Burešová, Zuzana and Middleton, Anna and Matsushita, Yoshitaka and Labuta, Jan and Ahsan, Aisha and Buimaga-Iarinca, Luiza and Karr, Paul A. and Bureš, Filip and Richards, Gary J. and Švec, Pavel and Mori, Toshiyuki and Ariga, Katsuhiko and Wakayama, Yutaka and Morari, Cristian and D'Souza, Francis and Jung, Thomas A. and Hill, Jonathan P.. (2021) Pyrazinacenes exhibit on-surface oxidation-state-dependent conformational and self-assembly behaviours. Communications Chemistry, 4 (1). p. 29.

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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.
Faculties and Departments:05 Faculty of Science > Departement Physik > Physik
UniBasel Contributors:Jung, Thomas A.
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:Nature Research
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:08 May 2023 12:30
Deposited On:08 May 2023 12:30

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