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-CH3C6H4 -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.
Easy entry into reduced Ar-BIANH2 compounds : a new class of quinone/hydroquinone-type redox-active couples with an easily tunable potential / M. Viganò, F. Ferretti, A. Caselli, F. Ragaini, M. Rossi, P. Mussini, P. Macchi. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - 20:44(2014), pp. 14451-14464. [10.1002/chem.201403594]
Easy entry into reduced Ar-BIANH2 compounds : a new class of quinone/hydroquinone-type redox-active couples with an easily tunable potential
F. FerrettiSecondo
;A. Caselli;F. Ragaini
;P. Mussini
;
2014
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-CH3C6H4 -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.File | Dimensione | Formato | |
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