Diphenylamino Group as an Effective Handle to Conjugated Donor−Acceptor Polymers through Electropolymerization

Abstract

[reaction: see text] The diphenylamino group is an effective handle for electropolymerization to give electron donor-acceptor conjugated polymers. In addition, interesting electrochromic and photoresponsive behavior of 13 has been investigated.

Electropolymerization and characterization of an alternatively conjugated donor–acceptor metallopolymer: Poly-[Ru(4′-(4-(Diphenylamino)phenyl)-2,2′:6′,2″-Terpyridine)2]2+

“…0.87 and 0.96 V in the second anodic scan were also observed, indicating that new electroactive species were formed after the first positive sweep. These results showed, in agreement with those of aniline and its derivatives [24][25][26], that the anodic oxidation of the monomer follows an E(CE) n -type mechanism [27], and that the oligomeric triphenylamine units, such as N,N,N′,N′-tetraphenyl-4,4′-diaminobiphenyl (TPB) [28], generated between two Ru (II)-terpyridine units are more easily oxidized than the parent compound. When the number of the CV cycle increased, the three triphenylaminebased anodic waves strengthened and combined into a sharp wave.…”

“…Introduction of an electron-deficient component into the electron-donating TPB molecule as the blocking group can efficiently prohibit the resonance interaction, resulting in the formation of alternatively conjugated donor-acceptor polymer [28]. Therefore, in this paper, it is believed that the waves at lower oxidation potentials are attributed to the formation of the radical cation species, which triggers the polymerization process and leads to chain extension, and the electron-deficient [Ru(TPY) 2 ] 2+ core plays a key role in the stabilization of the radical cation species.…”

Novel trends of electrochemical oxidation of amino-substituted triphenylamine derivatives

“…The stability of the cation radical varies markedly with para-substitution. Because of the low ionization potentials, reversible redox behavior and good film-forming properties [2,3], TPA-containing monomers [1,4] and polymers [3] have been synthesized and their charge injection and electroluminescent efficiency have been studied [4][5][6][7]. Today, the highly electron-rich TPA derivatives have been chosen as important candidates for electrical and optical applications such as organic photoconductors, electroluminescence and electrochromic devices [8][9][10].…”

“…The anodic oxidation pathway of TPA was well reported [1] and is shown in Eqs. (1)- (3). The electrogenerated cation radical TPA +Å dimerized to form tetraphenylbenzidine (TPB), which is more easily oxidized than the TPA molecule.…”

Substituent effects on the electrochemical and spectral characteristics of N,N,N′,N′-tetraaryl-p-phenylenediamine derivatives

“…Intramolecular electron transfer (ET) processes have been studied extensively in the mixed-valence (MV) systems [1][2][3]. The usually employed one-dimensional MV compounds contain two or more redox states connected via a r-or p-bridge molecule.…”