Electrochemical characterization of arylene vinylene oligomers containing triphenylamine and carbazole units

Abstract

Cyclic voltammetry (CV) has been used to investigate the electrochemical behavior of three arylene vinylene oligomers containing triphenylamine and carbazole units at the ends. The synthesis of oligomers was performed using Wittig reaction conditions, between 4-formyltriphenylamine or 3-formyl-N-hexyl-carbazole and two diphosphonium salts. The cyclic voltammograms, recorded in anodic range of potentials, revealed that the oligomers undergo quasi-reversible or irreversible redox processes. Polymer films were deposited on Pt electrode by CV and CPE (Controlled Potential Electrolysis) methods. The polymer films obtained by electrochemical polymerization methods show no solubility in all organic solvents and present similar FT-IR data with those polymers synthesized by chemical oxidative polymerization. Characterizations of the oligomers were made by 1 H-NMR spectroscopy, UV-Vis and fluorescence spectroscopy. Due to the lack of their solubility, the polymers obtained by electrochemical methods were characterized only by FT-IR spectroscopy.

Synthesis, Electrochemistry, and Photophysical Studies of Ruthenium(II) Polypyridine Complexes with D–π–A–π–D Type Ligands and Their Application Studies as Organic Memories

“…The electrochemical dataa re summarized in Table 1, and the cyclic voltammogram of complex 3 is shown in Figure 3. Accordingt ot he previouss tudies on triarylamine, [20,24] and with the reference to the oxidative couple of the ligand L3 at + 0.9 Vv ersus SCE ( Figure S4 in the Supporting Information), the oxidation couples are tentatively assigned as the oxidation of the triarylamine moiety.I ti s worthwhile to note that the potentials for oxidation are found to vary with the substituents on the triarylamine group for complexes 2-4 in dichloromethane. The ease of oxidation follows the trend complexes 3 (+ 0.88 V) > 4 (+ 0.93 V) > 2 (+ 1.01 V), as the triarylamine moiety appended with the polyphenylbenzene moiety (i.e.,c omplexes 3 and 4)i sabetter electron donor than that of the phenylalkynyl moiety (i.e., complex 2).…”

Deep Red to Near‐Infrared Emitting Rhenium(I) Complexes: Synthesis, Characterization, Electrochemistry, Photophysics, and Electroluminescence Studies

“…For complexes 1 and 3 – 5 , a second irreversible wave at +1.41 to +1.48 V was attributed to the further oxidation of the triarylamine group 23. For complex 2 , the irreversible wave at around +1.29 V was assigned to the oxidation of the carbazole groups 23b. In addition, complex 2 showed a broad irreversible oxidation wave at about +1.72 V, owing to the oxidation process of Re I to Re II mixed with carbazole‐based characters 23.…”

Synthesis and Optoelectronic Characterization of Some Star-Shaped Oligomers with Benzene and Triphenylamine Cores

“…The anodic oxidation of triphenylamine and its derivatives was extensively studied starting from 1966 [39–42]. As a conclusion of these studies, TPA-based oligomers fall in the category of multistep processes involving electrochemical-chemical-electrochemical (ECE) reactions.…”