Electrosynthesis of Aromatic Poly(amide-amine) Films from Triphenylamine-Based Electroactive Compounds for Electrochromic Applications

Abstract

Two electropolymerizable monomers with a methoxytriphenylamine core linked via amide groups to two triphenylamine (TPA) or N-phenylcarbazole (NPC) terminal groups, namely 4,4 -bis(4-diphenylaminobenzamido)-4 -methoxytriphenylamine (MeOTPA-(TPA) 2 ) and 4,4 -bis(4-(carbazol-9-yl)benzamido)-4 -methoxytriphenylamine (MeOTPA-(NPC) 2 ), were synthesized and characterized by FTIR and 1 H NMR spectroscopy, mass spectrometry, and cyclic voltammetry. The electrochemical polymerization reactions of these MeOTPA-cored monomers over indium tin oxide (ITO) electrode allow the generation of electroactive poly(amide-amine) films. The electro-generated polymer films exhibited reversible redox processes and multi-colored electrochromic behaviors upon electro-oxidation, together with moderate coloration efficiency and cycling stability. The optical density changes (∆OD) were observed in the range of 0.18-0.68 at specific absorption maxima, with the calculated coloration efficiencies of 42-123 cm 2 /C. Single-layer electrochromic devices using the electrodeposited polymer films as active layers were fabricated for the preliminary investigation of their electrochromic applications.

Electrochromism in Electropolymerized Films of Pyrene-Triphenylamine Derivatives

“…This decreases the experimental time and cost and partially solves the solubility problem of some compounds. A large number of electropolymerized films have been prepared from monomers functionalized with thiophene or carbazole derivatives [22,23,24,25,26,27,28]. In addition, triphenylamine groups have been used as polymerizable units to prepare thin films of organic and metal complexes by electropolymerization [29,30,31,32].…”

Electrochromic Devices Based on Poly(2,6-di(9H-carbazol-9-yl)pyridine)-Type Polymer Films and PEDOT-PSS

“…During the last decade, several CPs, such as polythiophenes (PTh) [18], polycarbazoles (PCz) [19,20], polytriphenylamines [21,22], polyanilines (PANI) [23], polyindoles [24,25], polyazulenes [26], and polyimides [27] have been widely studied for use as electrochromic materials. Among these CPs, PCz showed a light colour in the neutral state and a deep colour in oxidized state.…”

Applications of Poly(indole-6-carboxylic acid-co-2,2′-bithiophene) Films in High-Contrast Electrochromic Devices

“…Among them, the applications of conjugated polymers in developing high contrast electrochromic devices are currently attractive due to their energy-saving and light control properties. During the last decade, the most frequently studied electrochromic polymers are polythiophenes [14,15], polycarbazoles [16,17], polyindoles [18], polyanilines [19], polytriphenylamine [20], and polypyrroles [21]. Among them, polyindoles have several benefits such as high conductivity, facile polymerization from organic or aqueous media, and good chemical stability.…”