Organic Mixed Valence Systems. II. Two-Centers and Three-Centers Compounds with Meta Connections around a Central Phenylene Ring

This paper is devoted to two new aromatic polyamines derived from p -EFTP (5‘-(4-(bis(4-ethylphenyl)amino)phenyl)- N, N, N ‘, N ‘-tetrakis(4-ethylphenyl)-1,1‘:3‘,1‘‘-terphenyl-4,4‘‘-diamine) and exhibiting meta connections around a central phenylene ring. In p -EFDP (5‘-phenyl-( N, N, N ‘, N ‘-tetrakis(4-ethylphenyl)-1,1‘:3‘,1‘‘-terphenyl-4,4‘‘-diamine) there are only two redox sites instead of three. Upon partial oxidation, an intervalence transition is observed from which an electronic coupling very similar to the one of p -EFTP is obtained. In p -FADP ( N, N, N ‘, N ‘, N ‘‘, N ‘‘-hexakis(4-ethylphenyl)-1,1‘:3‘,1‘‘-terphenyl-4,4‘‘,5‘ triamine) one finds two redox sites of the N, N ‘-bis(4-ethylphenyl)-4-aminobiphenyl type, and one redox site of the triphenylamine type. The analysis of the electrochemical behavior and of the intervalence transitions in the mono- and dioxidized species allows the distinction among the different types of electron transfer.