Electrosynthesis and Photoelectrochemistry of Bis(triarylamine)-Based Polymer Electrochromes

Abstract

Two electroactive arylamine compounds with a methoxy-substituted bistriphenylamine core connected via amide linkages to two triphenylamine (TPA) or N-phenylcarbazole (NPC) end-groups, i.e. bis{N-[4-(4-diphenylaminobenzamido)phenyl]-N'-(4-methoxyphenyl)}-1,4-phenylenediamine [(MeO) 2 TPPA-(TPA) 2 ] and bis{N-[4-(4-carbazol-9-ylbenzamido)phenyl]-N'-(4methoxyphenyl)}-1,4-phenylenediamine [(MeO) 2 TPPA-(NPC) 2 ], were synthesized and used to build up triarylamine-based polymeric films on indiun-tin oxide (ITO) electrode via electrochemical polymerization. Due to the triarylamine-rich polymer matrix, the electro-synthesized polymer films exhibit multi-staged redox processes and multi-colored anodic electrochromic behaviors. The polymer films also show strong near-infrared absorption in the first oxidation state. They possess high coloration efficiency and good cycling stability, especially when switched between neutral and first or second oxidation states. For comparison, bis{N-[4-(benzamido)phenyl]-N'-(4-methoxyphenyl)}-1,4-phenylenediamine [(MeO) 2 TPPA-(Ph) 2 ] was also prepared as a model compound and characterized with the electrochemical and electro-optical properties.

Fast Switching Triphenylamine-Based Electrochromic Polymers with Fluorene Core: Electrochemical Synthesis and Optoelectronic Properties

“…These materials could meet the demands of electrochromic display devices contrast to some of (Table I) triphenylamine based polymers in literature. Thus, we could infer the fruitful effect of utilization of a planar fluorene core (compared to TPA cored [36][37][38]33 ) and azomethine linkage interms of lowering of both the band gap and the switching time.…”

Electrochromic properties of pyrene conductive polymers modified by chemical polymerization

“…This paper introduces different conductive groups to pyrene to improve its electrochromic properties. In regard to the use of Suzuki coupling and Stille coupling, the polymerization of 1,6dibromopyrene with triphenylamine, thiophene, thiophene derivatives and EDOT form ve conductive polymers of polyimides 37 and polythiophenes, 38,39 and the ve conjugated conductive polymers are named poly(2-(pyren-1-yl)thiophene) (PPYTP), poly(5…”

“…This paper introduces different conductive groups to pyrene to improve its electrochromic properties. In regard to the use of Suzuki coupling and Stille coupling, the polymerization of 1,6-dibromopyrene with triphenylamine, thiophene, thiophene derivatives and EDOT form five conductive polymers of polyimides 37 and polythiophenes, 38,39 and the five conjugated conductive polymers are named poly(2-(pyren-1-yl)thiophene) (PPYTP), poly(5-(pyren-1-yl)-2,3-dihydrothieno[3,4- b ][1,4]dioxine) (PPYEDOT), poly( N -(4-(diphenylamino)phenyl)-4-(pyren-1-yl)benzamide) (PBPYTPA), poly(5-(pyren-1-yl)-2,2′-bithiophene) (PPYBTP) and poly(5-(pyren-1-yl)-2,2′:5′,2′′-terthiophene) (PPYTTP). Ultraviolet-visible absorption spectroscopy, cyclic voltammetry, theoretical calculations and spectroelectrochemical experiments were used to study the properties of the polymers.…”

Electrodeposited Copolymers Based on 9,9′-(5-Bromo-1,3-phenylene)biscarbazole and Dithiophene Derivatives for High-Performance Electrochromic Devices

“…Organic, conjugated polymers belong to organic electrochromic materials. Polyimides [ 26 ], polycarbazoles [ 27 , 28 , 29 ], polythiophenes [ 30 , 31 ], polyindoles [ 32 , 33 ], poly(dioxythiophene)s [ 34 , 35 ], polytriphenylamines [ 36 , 37 ], and polythiadiazoles [ 38 ] are the main organic conjugated polymers used in several organic ECDs. Among them, polycarbazoles have attracted increased attention owing to their conspicuous absorption in the UV–Vis zone, good photo- and electroactive properties, and high hole-transporting ability.…”