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9,10-Anthraquinones Disubstituted with Linear Alkoxy Groups: Spectroscopy, Electrochemistry, and Peculiarities of Their 2D and 3D Supramolecular Organizations

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cris.lastimport.scopus2024-02-12T20:14:59Z
dc.abstract.enSpectroscopic, electrochemical, and structural properties of 2,6-dialkoxy-9,10-anthraquinones (Anth-OCn, n = 4, 6, 8, 10, and 12) of increasing alkoxy substituents length were investigated. UV–vis spectroscopy showed a substitution-induced bathochromic shift of the least energetic band from 325 nm in the case of unsubstituted anthraquinone to ca. 350 nm for the studied derivatives. Similarly as unsubstituted anthraquinone, the studied compound showed two reversible one electron reductions to a radical anion and spinless anions, respectively. The first reduction was affected by electron-donating properties of the substituents, its potential being shifted to ca. −1.5 V (vs Fc/Fc+), i.e., by 80 to 95 mV as compared to the case of unsubstituted anthraquinone. This corresponded to a decrease of |EA| from 3.27 to 3.19–3.17 eV. The experimental spectroscopic and electrochemical data were in full agreement with the DFT calculations. The introduction of the alkoxy substituent improved solution processibility of the studied compounds and facilitated the formation of their ordered supramolecular 2D aggregation on HOPG as well as single crystal growth from solutions. Comparative structural investigations carried out on single crystals and monolayers deposited on HOPG revealed two, mutually related, effects of the substituent length on the resulting supramolecular organization. The first one concerns both the 2D organization in the monolayers and 3D molecular arrangement in crystals: increasing substituent length evolution of the structure occurs from herringbone-type to lamellar. The second effect, observed in monolayers of the derivatives with longer substituents, concerns gradual evolution of their lamellar structures with increasing substituent length. This evolution is induced by the structure of the graphite substrate and involves increasing correlation of the molecules orientation (anthraquinone cores as well as alkoxy substituents) with the symmetry of the graphite substrate. As a result, their 2D and 3D structures become dissimilar.
dc.affiliationUniwersytet Warszawski
dc.contributor.authorProń, Adam
dc.contributor.authorMaranda-Niedbała, Agnieszka
dc.contributor.authorZagórska, Małgorzata
dc.contributor.authorDrapała, Jakub
dc.contributor.authorSkórka, Łukasz
dc.contributor.authorKotwica, Kamil
dc.contributor.authorNowakowski, Robert
dc.contributor.authorKrzyżewska, Klaudyna
dc.contributor.authorJarzembska, Katarzyna
dc.date.accessioned2024-01-24T15:36:25Z
dc.date.available2024-01-24T15:36:25Z
dc.date.copyright2020-12-03
dc.date.issued2020
dc.description.accesstimeAT_PUBLICATION
dc.description.financePublikacja bezkosztowa
dc.description.number49
dc.description.versionFINAL_PUBLISHED
dc.description.volume36
dc.identifier.doi10.1021/ACS.LANGMUIR.0C02586
dc.identifier.issn0743-7463
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/100101
dc.identifier.weblinkhttps://pubs.acs.org/doi/10.1021/acs.langmuir.0c02586
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofLangmuir
dc.relation.pages15048-15063
dc.rightsCC-BY
dc.sciencecloudnosend
dc.subject.enMonolayers
dc.subject.enSupramolecular chemistry
dc.subject.enSubstituents
dc.subject.enRedox reactions
dc.subject.enReaction products
dc.title9,10-Anthraquinones Disubstituted with Linear Alkoxy Groups: Spectroscopy, Electrochemistry, and Peculiarities of Their 2D and 3D Supramolecular Organizations
dc.typeJournalArticle
dspace.entity.typePublication