Solution-processable, high-T_g, ambipolar polyimide electrochromics bearing pyrenylamine units

Abstract

Two new pyrenylamine-based polyimides were prepared from the polycondensation reaction of N,N-di(4-aminophenyl)-1-aminopyrene with pyromellitic dianhydride (PMDA) or 1,4,5,8naphthalenetetracarboxylic dianhydride (NTDA). The polyimide derived from PMDA is soluble in hot N-methyl-2-pyrrolidone and can be solution-cast into a flexible and strong film. The polyimides showed high glass transition temperatures (T g > 364 C) and high thermal stability. Cyclic voltammetry studies revealed that these two polyimides were ambipolar; they showed well-defined and reversible redox couples during both p-and n-doping processes, together with multi-electrochromic behaviors. The polymer films also exhibited high coloration efficiency, high redox stability, and fast response time.

Synthesis and Characterization of a Pyromellitic Diimide-Based Polymer with C- and N-Main Chain Links: Matrix for Solution-Processable n-Channel Field-Effect Transistors

“…Among the thermal and chemical imidizations, we have chosen the chemical imidization method to obtain highly soluble polymer, as observed by the Hsiao and co-workers. 28 As expected, the title polymer showed very good solubility in chloroform, toluene and chlorobenzene, which enables spin coating from solution.…”

Thermal, optical, electrochemical, and electrochromic characteristics of novel polyimides bearing the Acridine Yellow moiety

“…The highest reduction potential, that is, À0.74 V vs ferrocene (Fc) (peak onset), was obtained for PI-1, what is a direct consequence of high resonance energy and effective delocalization of negative charge. On the other hand, PI-3 underwent reduction at À1.88 V peak potential vs. Fc, what is a result of recently described [13] relative lowering of reduction peak potential, when a system with less number of aromatic fused rings is introduced.…”

“…For each polyimide measured in solution a fully reversible reduction process towards the formation of an anion radical according to mechanism put forward by S.-H. Hsiao and Kung [13] was detected. The highest reduction potential, that is, À0.74 V vs ferrocene (Fc) (peak onset), was obtained for PI-1, what is a direct consequence of high resonance energy and effective delocalization of negative charge.…”

Structure and properties of new highly soluble aromatic poly(etherimide)s containing isopropylidene groups

“…[1][2][3] This unique combination of properties makes PIs ideal for a variety of applications, for example, in microelectronics, microelectromechanical systems, aerospace and photoelectronics or as gas separation membranes, materials for memory devices, alignment layers in liquid crystal displays, and redox-active, electrochromic polymers. [3][4][5][6] Although many excellent polyimides are known and commercially available, new polyimides are emerging as research continues on the chemical structure-property correlations and on the search for new compounds with unique combinations of properties for special applications. Recently, particular attention has been paid to new materials and technologies for gas separation applications because of environmental concerns and economic interests.…”