Pyrazinacenes exhibit on-surface oxidation-state-dependent conformational and self-assembly behaviours
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F21%3A39917652" target="_blank" >RIV/00216275:25310/21:39917652 - isvavai.cz</a>
Result on the web
<a href="http://10.1038/s42004-021-00470-w" target="_blank" >http://10.1038/s42004-021-00470-w</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1038/s42004-021-00470-w" target="_blank" >10.1038/s42004-021-00470-w</a>
Alternative languages
Result language
angličtina
Original language name
Pyrazinacenes exhibit on-surface oxidation-state-dependent conformational and self-assembly behaviours
Original language description
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.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
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Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2021
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Communications Chemistry
ISSN
2399-3669
e-ISSN
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Volume of the periodical
4
Issue of the periodical within the volume
1
Country of publishing house
GB - UNITED KINGDOM
Number of pages
10
Pages from-to
29
UT code for WoS article
000627390300001
EID of the result in the Scopus database
2-s2.0-85102370056