Synthesis and Analysis of Triphenylamine: A Review

Abstract

In this paper, synthesis and characteristic of arylaminetype molecules, particularly triphenylamine are discussed. An overview of the physical properties and chemical characteristics of these types of molecules is provided. Different synthesis methods and mechanisms involved for the production of these molecules and their analysis by HPLC are presented. Finally, a brief HPLC are presented. Finally, a brief HPLC note about their purifi cation is presented.Dans cet article, on analyse la synthèse et la caractéris-tique des molécules de type arylamine, et particulière-ment la triphénylamine. On donne un aperçu général des propriétés physiques et des caractéris-tiques chimiques de ce type de molécules. Plusieurs méthodes et mécanismes de synthèse intervenant dans la production de ces molécules et leur analyse par HPLC sont présentés. Enfi n, leur purifi cation est brièvement décrite.

Triphenylamine and some of its derivatives as versatile building blocks for organic electronic applications

“…Different synthetic methods are known for TPA‐type molecules. They can be obtained for example by modifications of the Ullmann condensation reaction (1903) through the nucleophilic substitution of an aryl halide in the presence of a copper catalyst and a base . More recently, the use of palladium catalysts with phosphine ligands was found to be a successful approach for the synthesis of TPA derivatives such as mixed secondary arylamines obtained from amination of aryl halides, allowing milder reaction conditions and easier separation and crystallization steps.…”

Redox initiated cationic polymerization: Silane‐N‐aryl heteroaromatic onium salt redox couples

“…The acridan, 12 , formed by reduction of the parent 10‐phenylacridinium salt can be characterized as a bridged triarylamine and is closely structurally and electronically related to triphenylamine. Triphenylamine is only very weakly basic ( K b ≤ 10 −10 ) so that its protonated onium salts are fully ionized in water and behave as Brønsted acids 27. For this reason, 12 does not inhibit the cationic polymerizations of highly reactive monomers such as epoxides, oxetanes and vinyl ethers.…”

“…Triphenylamine is only very weakly basic (K b 10 À10 ) so that its protonated onium salts are fully ionized in water and behave as Brønsted acids. 27 For this reason, 12 does not inhibit the cationic polymerizations of highly reactive monomers such as epoxides, oxetanes and vinyl ethers. A similar argument can be advanced for the reduction product, 17, of 2-phenylisoquinolinium salts.…”

Influence of donor-acceptor conjugation between thiophene-phthalazinone structures containing Sp3 CN bond on the frontier orbital levels and optic-electronic properties

“…In the past decades, the intrinsic characteristics of donor–acceptor (D–A) conjugated polymers containing Sp 3 CN bond have been widely studied as important organic semiconductor materials for optoelectronic applications, such as light‐emitting diodes, polymer solar cells, and organic field effect transistors . The classical structures, such as polyaniline and triphenylamine, are shown in Figure .…”

“…Also, polymeric materials based on triphenylamine units have been widely used as semiconductor materials for electro‐optics applications. The structure feature of triphenylamine is that the electron‐rich nitrogen atom links with three π‐conjugated phenyl groups, resulting in its narrower band gaps than that of non‐doped polyaniline. Incorporating triphenylamine into polymer backbones with π‐conjugated system could obtain excellent charge‐transport, hole‐transporting, and electroluminescence properties with controllable band gaps .…”