Collection of Czechoslovak Chemical Communications p. 1403 - 1418 (2000)
Update date:2022-09-26
Topics: Anodic Oxidation Spectroscopic Characterization Electrochemical characterization
Faber, Rene
Mielke, G. Felix
Rapta, Peter
Stasko, Andrej
Nuyken, Oskar
Fluorenylidene-linked triarylamines, potential hole-transporting materials, have been prepared by the palladium-catalyzed Hartwig-Buchwald animation. Their redox and spectral properties were investigated in solution, applying cyclic voltammetry, UV-VIS and WR spectroscopy, and in situ spectroelectrochemical measurements. N,N,N′,N′-Tetraphenylbenzidine (1), N,N′-di(1-naphthyl)-N,N′-diphenylbenzidine (2), and triphenylamine (3) served as model substances in the study of the synthesized complex compounds 4 and S. In structure 4, two triphenylamine centres are linked with a non-conjugated fluorene bridge; in structure 5, two tetraarylbenzidine skeletons with two nitrogens are linked with a conjugated biphenyl-bridge system. In addition, structure 5 contains a non-conjugated fluorene bridge. The presence of the fluorene moiety in the molecular design has a significant influence on the investigated properties of the new materials. In the anodic oxidation of the tetraarylbenzidine-type compounds (1, 2, and 5), two well-defined reversible oxidation peaks were observed. However, the oxidation of the triphenylamine-type structures (3 and 4) is more complex, due to fast consecutive reactions. The dimer-like structures (4 and 5) are characterized by two independent oxidation centres that are simultaneously oxidized at approximately the same potentials. This was confirmed by quantitative cyclovoltammetric as well as UV-VIS investigations.
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