Corecarbo-mer of an Extended Tetrathiafulvalene: Redox-Controlled Reversible Conversion to acarbo-Benzenic Dication

carbo-Benzene is an aromatic molecule devised by inserting C(2)units within each C-C bond of the benzene molecule. By integrating the correspondingcarbo-quinoid core as bridging unit in a pi-extended tetrathiafulvalene (exTTF), it is shown that acarbo-benzene ring can be reversibly formed by electro...

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Published inChemistry : a European journal Vol. 26; no. 47; pp. 10707 - 10711
Main Authors Listunov, Dymytrii, Hammerich, Ole, Caballero-Quintana, Irving, Poater, Albert, Barthes, Cecile, Duhayon, Carine, Larsen, Mie Hojer, Maldonado, Jose-Luis, Ramos-Ortiz, Gabriel, Nielsen, Mogens Brondsted, Maraval, Valerie, Chauvin, Remi
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 21.08.2020
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
CARBO-CYCLOHEXADIENES
carbo-mer
AROMATICITY
quinoid
SELF-ASSEMBLED MONOLAYERS
redox behavior
BEHAVIOR
alkyne
extended tetrathiafulvalene
COMPLEXATION
DERIVATIVES
TTF ANALOGS
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Summary:carbo-Benzene is an aromatic molecule devised by inserting C(2)units within each C-C bond of the benzene molecule. By integrating the correspondingcarbo-quinoid core as bridging unit in a pi-extended tetrathiafulvalene (exTTF), it is shown that acarbo-benzene ring can be reversibly formed by electrochemical reduction or oxidation. The so-calledcarbo-exTTF molecule was thus experimentally prepared and studied by UV-visible absorption spectroscopy and cyclic voltammetry, as well as by X-ray crystallography and by scanning tunneling microscopy (STM) on a surface of highly oriented pyrolytic graphite (HOPG). The molecule and its oxidized and reduced forms were subjected to a computational study at the density functional theory (DFT) level, supportingcarbo-aromaticity as a driving force for the formation of the dication, radical cation, and radical anion. By allowing co-planarity of the dithiolylidene rings andcarbo-quinoidal core,carbo-exTTFs present a promising new class of redox-active systems.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202001700