Anodic Oxidation of Novel Hole-Transporting Materials Derived from Tetraarylbenzidines. Electrochemical and Spectroscopic Characterization

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Title:Anodic Oxidation of Novel Hole-Transporting Materials Derived from Tetraarylbenzidines. Electrochemical and Spectroscopic Characterization
Creators:
Fáber, René
Mielke, G. Felix
Rapta, Peter
Staško, Andrej
Nuyken, Oskar
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 65, 9, pp. 1403-1418
Uncontrolled Keywords:Hole-transporting materials, Cyclic voltammetry, Electrochemistry, Triarylamines, Hartwig-Buchwald amination, EPR/UV-VIS spectroelectrochemistry, Tetraarylbenzidines

Abstract

Fluorenylidene-linked triarylamines, potential hole-transporting materials, have been prepared by the palladium-catalyzed Hartwig-Buchwald amination. Their redox and spectral properties were investigated in solution, applying cyclic voltammetry, UV-VIS and EPR spectroscopy, and <i>in situ</i> spectroelectrochemical measurements. <i>N</i>,<i>N</i>,<i>N'</i>,<i>N'</i>-Tetraphenylbenzidine (<strong>1</strong>), <i>N</i>,<i>N'</i>-di(1-naphthyl)-<i>N</i>,<i>N'</i>-diphenylbenzidine (<strong>2</strong>), and triphenylamine (<strong>3</strong>) served as model substances in the study of the synthesized complex compounds <strong>4</strong> and <strong>5</strong>. In structure <strong>4</strong>, two triphenylamine centres are linked with a non-conjugated fluorene bridge; in structure <strong>5</strong>, two tetraarylbenzidine skeletons with two nitrogens are linked with a conjugated biphenyl-bridge system. In addition, structure <strong>5</strong> 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 (<strong>1</strong>, <strong>2</strong>, and <strong>5</strong>), two well-defined reversible oxidation peaks were observed. However, the oxidation of the triphenylamine-type structures (<strong>3</strong> and <strong>4</strong>) is more complex, due to fast consecutive reactions. The dimer-like structures (<strong>4</strong> and <strong>5</strong>) 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. <p>

Title:Anodic Oxidation of Novel Hole-Transporting Materials Derived from Tetraarylbenzidines. Electrochemical and Spectroscopic Characterization
Creators:
Fáber, René
Mielke, G. Felix
Rapta, Peter
Staško, Andrej
Nuyken, Oskar
Uncontrolled Keywords:Hole-transporting materials, Cyclic voltammetry, Electrochemistry, Triarylamines, Hartwig-Buchwald amination, EPR/UV-VIS spectroelectrochemistry, Tetraarylbenzidines
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:65
Number:9
Page Range:pp. 1403-1418
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20001403UNSPECIFIED
ID Code:1725
Item Type:Article
Deposited On:06 Feb 2009 17:12
Last Modified:06 Feb 2009 16:12

Citation

Fáber, René; Mielke, G. Felix; Rapta, Peter; Staško, Andrej; Nuyken, Oskar (2000) Anodic Oxidation of Novel Hole-Transporting Materials Derived from Tetraarylbenzidines. Electrochemical and Spectroscopic Characterization. Collection of Czechoslovak Chemical Communications, 65 (9). pp. 1403-1418. ISSN 0010-0765

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