Synthesis and Characterization of Linear, Branched and Hyperbranched Triphenylamine-Based Polyazomethines

Abstract

Novel triphenylamine-based linear, hyperbranched and branched conjugated polyazomethines have been synthesized by free-catalyst solution polycondensation of 1,4-diaminobenzene with 4,4 -diformyl triphenylamine, 4,4 ,4 -triformyl triphenylamine and their mixture in different molar ratios. Linear polyazomethine has a good solubility in organic solvents while branched and hyperbranched polymers are partially soluble. A wholly soluble hyperbranched polyazomethine was obtained by end-capping of polymer at gelation point using a monofunctional aromatic amine, p-anisidine. Characterization of all polymers was made by 1 H-NMR, FT-IR and UV-Vis and photoluminescence spectroscopy and thermal methods. Electrochemical behavior of polymers was studied by cyclic voltammetry using thin films cast from THF solution on a platinum disc working electrode in acetonitrile solvent and tetrabutylammonium tetrafluoroborate as electrolyte.

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

“…Dioxane and tetrahydrofuran (THF) were dried on sodium wire and distilled under nitrogen just before use. 4-Formyl triphenylamine [22] and 4,4′,4′′-triformyl triphenylamine [23–25] were obtained by formylation of TPA according to the reported methods. 4-Formyl-N,N′-bis(4-bromophenyl) aniline [26], tris (4-iodophenyl) amine [27] and vinyl triphenylamine [28] were synthesized and purified according to the literature procedures.…”

Linear and hyperbranched triphenylamine-based polyarylenevinylenes: a comparative optoelectronic study

“…[19] In a previous paper, we have synthesized and characterized linear, branched, and hyperbranched polyimines (isoelectronic structure of PPVs) using bis-and tris-formyl triphenylamine and 1,4-diaminobenzene as condensation monomers. [20] We have observed that electronic conjugation in the hyperbranched polymers is more reduced than in linear polymers due to sterical hindrances; however, the aggregation of polymer chains in solution was not observed. As a continuation of this study, in this article, we report the synthesis of linear and branched PPVs and compare their optical, and electrochemical properties.…”

“…4,4′-Diformyl triphenylamine and 4,4′,4′′-triformyl triphenylamine were synthesized starting from triphe nylamine by formylation, according to the methods reported in the literature. [20][21][22] All solvents were commercially products and were used as received or purified or dried by known methods. 2.1.1.…”

“…It is clear that conjugation length was not enhanced by branching due to higher sterical hindrances, more compact structure and entanglements, as well as in the case of branched polyimines. [20] …”

Polyazomethines with Triphenylamine Groups Synthesized by Suzuki Polycondensation Reactions

“…Thus, Niu et al [27][28][29] [31,32] have used 4,4 -diformyl-TPA in reaction with 4,4 -dioxyaniline, 4,4 -(1,3-phenylenedioxy)aniline or 1,4-phenylenediamine. We have also synthesized linear, branched and hyperbranched PAMs by solution polycondensation of bis-or trisaldehyde triphenylamine with aromatic diamines and studied the influence of chain architecture on their electrophysical properties [33]. All these materials are wholly aromatic polymers, have good solubilities and interesting electrophysical properties.…”