Synthesis, properties, and self-polymerization of hole-transporting carbazole- and triphenylamine-based hydrazone monomers

Abstract

Synthesis, optical, thermal, electrochemical, and photoelectrical properties of new carbazole-and triphenylamine-based hydrazones with reactive vinyl groups are reported. Self-polymerization in the solid state of the synthesized monomers was studied by differential scanning calorimetry (DSC) and IR spectrometry. Molecular weights of the soluble polymers were determined by gel chromatography. The synthesized compounds were characterized by 1 H and 13 C NMR, IR, UV/VIS, fluorescence, and mass spectrometries, as well as by cyclic voltammetry. The synthesized carbazole-and triphenylamine-based hydrazones form glasses with the glass transition temperatures ranging from 83 to 118°C, as was elucidated by DSC. Their thermal degradation starts above 270°C, as was revealed by thermogravimetric analysis. The ionization potentials of the films of carbazole-and triphenylamine-based hydrazones, measured by the electron photoemission in air technique, range from 5.32 to 5.65 eV. Hole-drift mobilities in amorphous layers of the monomers, estimated by xerographic time of flight technique, approach 10 À3 cm 2 /Vs at high electric fields.

Facile and straightforward synthesis of Hydrazone derivatives

“…One of the most promising organic hole transporting materials are aromatic hydrazones. Recently, some researchers have reported the synthesis of polymeric hydrazones with remarkable properties such as high glass transition temperatures, good filmformation and moderate charge transport [6].…”

Complexes of Gold(III) with Hydrazones Derived from Pyridoxal: Stability, Structure, and Nature of UV-Vis Spectra

“…However, ferric complexes of PL-derived hydrazones may have cytotoxic effects because of the induction of oxidative stress [17,18]. In general, hydrazones are versatile compounds gaining attention not only because of their biological activity, but also for their catalytic and fluorescent properties, which can be used for metal recognition and glass and phosphor production [19][20][21]. PLP-derived hydrazones have received less attention with regard to their biological activity than PL hydrazones.…”

Synthesis, crystal structure, Hirshfeld surface analysis, DFT, molecular docking and molecular dynamic simulation studies of (E)-2,6-bis(4-chlorophenyl)-3-methyl-4-(2-(2,4,6-trichlorophenyl)hydrazono)piperidine derivatives

“…In modern days, arylhydrazones are studied and found considered as the best p-type semiconductors among the semiconductors due to rapid charge transport, high photosensitivity, simple synthesis and low cost in its structure. Thus, hole-transport properties are present in arylhydrazones and are used as organic semiconductors in electrophotographic, memory storage, photovoltaic devices and organic light emitting diodes [13] , [14] , [15] , [16] , [17] , [18] . Hydrazone compound are the current interest in many chemical processes such as sensors, pharmaceutical activities and nonlinear optical materials due to its high value in hyperpolarizability [19] , [20] .…”