Pyrazinacenes exhibit on-surface oxidation-state-dependent conformational and self-assembly behaviours.
Journal
Communications chemistry
ISSN: 2399-3669
Titre abrégé: Commun Chem
Pays: England
ID NLM: 101725670
Informations de publication
Date de publication:
10 Mar 2021
10 Mar 2021
Historique:
received:
17
11
2020
accepted:
09
02
2021
entrez:
25
1
2023
pubmed:
10
3
2021
medline:
10
3
2021
Statut:
epublish
Résumé
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.
Identifiants
pubmed: 36697553
doi: 10.1038/s42004-021-00470-w
pii: 10.1038/s42004-021-00470-w
pmc: PMC9814942
doi:
Types de publication
Journal Article
Langues
eng
Pagination
29Subventions
Organisme : MEXT | Japan Society for the Promotion of Science (JSPS)
ID : JP15K13684
Informations de copyright
© 2021. The Author(s).
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