Supramolecular Derivatives of 9,10‐Anthraquinone. Electrochemistry at Regular‐ and Low Ionic Strength and Complexing Properties

Abstract

Three newly synthesized polyanthraquinone derivatives: 7,13-bis(9,10-dioxo-1-anthryl)-1,4,10-trioxa-7,13-diazacyclopentadecane, (AQ)A 2 15C5, 7,16-bis(9,10-dioxo-1-anthryl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane, (AQ)A 2 18C6, and tris[(9,10-diokso-1-antryl)-aminoethyl]amine, (AQNet) 3 N, were examined by cyclic and normal pulse voltammetry. All anthraquinone groups in these compounds were electroactive and formed the radicals and dianions similarly to simple anthraquinone. The differences between the voltammograms obtained in the absence and presence of supporting electrolyte are discussed, and the diffusion coefficients of the compounds and the rates of the chemical reactions following the first reduction step were evaluated. (AQNet) 3 N appears to be a good model compound for multi electron transfers in aprotic solvents. It offers two consecutive nearly reversible 3-electron redox systems: 0/À 3 and À 3/À 6. The interactions of the radicals and dianions of the above compounds with alkali metal cations were examined.

Synthesis and characterization of new redox-active polymers based on 10-(1,3-dithiol-2-ylidene)anthracen-9(10H)-one derivatives

“…3a). Similar findings are presented in literature [20]. Another reduction reaction occurs at the edge of the electrochemical stability of the DMF-based electrolyte (À2.1 V vs. Fc þ /Fc), which is most likely attributed to the reduction of the aromatic anthracene core of the monomer unit.…”

Enhanced electrocatalytic reduction of oxygen with a molecule having multi-quinone moieties adsorbed in the nanofiber film

“…Moreover, the peak potential shift toward negative direction has been observed in the first redox couple of AQ1 and AQ2 as compared with 9,10-AQ, which is related to the redox of anthraquinone moieties to a semiquinone radical. These voltammetric properties of AQ1 and AQ2 are totally similar with a previous observation for anthraquinones having multi-quinone moieties [32].…”

“…Chemical structure of anthraquinone derivatives used. anthraquinone groups, while for 9,10-AQ were an one-electron transfer process [32]. In terms of size, AQ1 and AQ2 molecules are larger than 9,10-AQ, that results in their diffusion coefficient are appropriately smaller (under identical conditions, the diffusion coefficient is inversely proportional to the molecule radius).…”

Heterogeneous proton-coupled electron transfer of a hydroxy-anthraquinone self-assembled monolayer

“…However, the redox mechanism is dependent on solvent, supporting electrolyte, electrode material, and pH [4]. In dry aprotic solvents, the cyclic voltammogram (CV) shows two consecutive one-electron redox steps [1,11,12], however, in aqueous media, the CV displays a single two-electron redox wave. The two redox waves seen in the dry aprotic environment overlap in aqueous solvents and result in a single peak, which is attributed to strong hydrogen bonding which stabilizes Q 2À over Q ÁÀ [1].…”