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Pyrazinacenes exhibit on-surface oxidation-state-dependent conformational and self-assembly behaviours
Authors: Miklík David | Mousavi S. Fatemeh | Burešová Zuzana | Middleton Anna | Matsushita Yoshitaka | Labuta Jan | Ahsan Aisha | Buimaga-Iarinca Luiza | Karr Paul A | Bureš Filip | Richards Gary J | Svec Pavel | Mori Toshiyuki | Ariga Katsuhiko | Wakayama Yutaka | Morari Cristian | D'Souza Francis | Jung Thomas A | Hill Jonathan P
Year: 2021
Type of publication: článek v odborném periodiku
Name of source: Communications Chemistry
Publisher name: Nature Publishing Group
Place: London
Page from-to: 29
Titles:
Language Name Abstract Keywords
cze Pyrazinaceny vykazují konformační a samoorganizující se chování závislé na povrchovém oxidačním stavu. Práce se zabývá studiem pyrazinacenů obsahujících dihydro-dekaazapentacenové a dihydro-oktaazatetracenové chromofory a porovnáním jejich vlastností při modelovém chování na oxidačním kovovém substrátu. Byla nalezena odlišná, na oxidačním stavu závislá konformační adaptace a samouspořádající se chování. Byly připraveny dekaazapentaceny a oktaazatetraceny a analyzováno jejich samoorganizující se chování v různých oxidačních stavech. Pyrazinaceny; samoorganizující se; redox-aktivní chromofory
eng 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-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 pi-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. Pyrazinacenes; self-assembly; redox-active chromophores

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