title: Easy entry into reduced Ar-BIANH2 compounds: a new class of quinone/hydroquinone-type redox-active couples with an easily tunable potential.
abstract: Ar-BIANH2 bearing different substituents on the aryl rings have been synthesized in high yield by reduction of the corresponding bis(aryl)acenaphthenequinonediimine (Ar-BIAN) compounds. The structure of p-CH3 C6 H4 -BIANH2 in the solid state was determined by X-ray diffraction. An exhaustive voltammetric investigation of the two parallel BIAN and BIANH2 series afforded a first rationalization of the redox properties of these molecules, highlighting their analogies with quinone/hydroquinone systems. Such analogies, in combination with the much more negative reduction potential range of Ar-BIAN compounds with respect to quinones, can afford to extend the range of reduction potentials so far obtainable by the use of quinones.
authors.affiliation: Dipartimento di Chimica, Università degli Studi di Milano via Golgi 19, 20133 Milano (Italy).
authors.forename: Marta
authors.initials: M
authors.lastname: Viganò
authors.forename: Francesco
authors.initials: F
authors.lastname: Ferretti
authors.forename: Alessandro
authors.initials: A
authors.lastname: Caselli
authors.forename: Fabio
authors.initials: F
authors.lastname: Ragaini
authors.forename: Manuela
authors.initials: M
authors.lastname: Rossi
authors.forename: Patrizia
authors.initials: P
authors.lastname: Mussini
authors.forename: Piero
authors.initials: P
authors.lastname: Macchi
keywords: N ligands; X-ray diffraction; cyclic voltammetry; electrochemistry; quinones; redox chemistry