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Abstract
Two series of polyamides and polyimides containing bulky trityl-substituted triphenylamine units were synthesized from condensation reactions of 4,4′-diamino-4′′-trityltriphenylamine with various dicarboxylic acids and tetracarboxylic dianhydrides, respectively. The polymers showed good solubility and film-forming ability. Flexible or robust films could be readily obtained via solution-casting. The use of aliphatic diacid or dianhydride reduces interchain charge transfer complexing and leads to colorless polyamide and polyimide films. These polymers showed glass-transition temperatures in the range of 206–336 °C. Cyclic voltammograms of the polyamide and polyimide films displayed reversible electrochemical oxidation processes in the range of 0–1.0 or 0–1.3 V. Upon oxidation, the color of polymer films changes from colorless to blue-green or blue. As compared to the polyimide counterparts, the polyamides showed lower oxidation potentials and thus a higher electrochromic stability and coloration efficiency. Simple electrochromic devices were also fabricated as a preliminary investigation for electrochromic applications of the prepared polymers.
Highlights
Aromatic polyamides and polyimides are classified as high performance polymers by their outstanding elevated thermal stability, high strength and stiffness, and broad chemical resistance [1,2,3,4,5,6,7,8]
Solubility improvements of aromatic polyamides and polyimides could be achieved by macromolecular engineering, mainly by designing and synthesizing new monomers [3,9,10]
According to the phosphorylation technique described by Yamazaki and co-workers [45], a series of polyamides 5a–5e were synthesized from the diamine monomer 3 with various aromatic or aliphatic dicarboxylic acids (4a−4e) by means of TPP and pyridine (Scheme 2)
Summary
Aromatic polyamides and polyimides are classified as high performance polymers by their outstanding elevated thermal stability, high strength and stiffness, and broad chemical resistance [1,2,3,4,5,6,7,8]. Due to the presence of packing-disruptive, three-dimensional triarylamine moieties, these polymers, especially for polyamides, are generally organosoluble and can be fabricated into amorphous thin film via solution-casting process This is helpful for their applications in optoelectronic devices. The incorporation of bulky trityl-substituted triphenylamine units increases the interchain spacing and reduces the packing efficiency, thereby increasing the intrinsic microporosity They exhibited a good gas separation performance. As a continuation of our devotion to research and developments in processable high performance polymers with electrochromic function, we synthesized and characterized some aromatic and semi-aromatic polyamides and polyimides containing trityl-substituted triphenylamine units, and the electrochemistry, spectroscopy, and electrochromic cycling stability of the polymer films were investigated. In addition to increased solubility caused by the incorporation of twisted nonplanar trityl substituent and triphenylamine group, the increased free volume was expected to allow better charge transfer at doping, and leading to fast switch speeds
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