Six star-shaped oligomers containing triphenylamine (D1–D3) and benzene unit (D4–D6) as cores have been synthesized by Wittig condensation or Heck coupling reaction using aromatic aldehydes and triphenylphosphonium salts or aromatic halogenated compounds with vinyl triphenylamine. All oligomers have well-defined molecular structure and high purity. Characterization of the oligomers was made by FT-IR, 1H-NMR spectroscopy, UV-Vis, and fluorescence spectroscopy. The electrochemical behavior was studied by cyclic voltammetry (CV). The cyclic voltammograms have revealed that oligomers undergo quasireversible or irreversible redox processes. The irreversible process is associated with electrochemical polymerization of oligomers by dimerization of unsubstituted triphenylamine groups. Thermal characterization was accomplished by TGA and DSC methods and evidenced that all oligomers were stable materials until 250°C and have formed stable molecular glasses after first heating scan.

Three imine macrocycles having rhomboidal shape were synthesized in good yields by [2+2] cyclocondensation reaction between equimolar quantities of (R,R)-1,2-diaminocyclohexane and 4,4'-bisformyl triphenylamine derivatives. The macrocycles structure was assigned by electrospray ionization mass spectrometry (ESI-MS), (1)H-NMR, and elemental analysis. UV, FTIR spectroscopy, and TG measurements were also used to characterize and prove the structure of these compounds. A conformational modification arising out of the rotation of triphenylamine group around the flexible cyclohexane-N bonds was observed in solution by (1)H-NMR and UV spectroscopy for all three macrocycles.

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The synthesis of triphenylamine-based polyarylenevinylene with linear and hyperbranched architecture is described. The synthetic route is based on Wittig polycondensation reaction at room temperature using as partners di-or tri-aldehyde of triphenylamine and bis-or tris-phosphonium salts. The polymers are separated as two fractions, one insoluble in chloroform and another one soluble in chloroform and insoluble in methanol. All polymers are obtained mostly in cis configuration, but cis linear polymers are thermally isomerized to corresponding trans structures, while branched structures are more thermally stable and isomerization process was not clearly evidenced. Characterization of the polymers was performed using NMR and FT-IR spectroscopy and thermal gravimetric analysis, while the optoelectronic properties were studied by UV-Vis and fluorescence and cyclic voltammetry, and compared with model compounds.