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URN etd-0216107-110655 Statistics This thesis had been viewed 2899 times. Download 1200 times. Author Chien-Chang Shih Author's Email Address No Public. Department Chemical Engineering Year 2006 Semester 1 Degree Master Type of Document Master's Thesis Language English Page Count 75 Title Synthesis, Photoluminescene and Electrochromism of Aromatic Polyamides and Polyimides with Pyrrole-Substituted Triphenylamino Groups Keyword Electrochromic characteristics Half-wave oxidation potential Half-wave oxidation potential Electrochromic characteristics Abstract 4-(N-Pyrroyle)aniline was synthesized by the nucleophilic fluoro-displacement reaction of 1-fluoro-4-nitrobenzene with pyrrole from sodium hydride medium in DMSO solvent, followed by palladium-catalyzed hydrazine reduction. Further amination reaction between 4-(N-pyrroyle)aniline and 1-fluoro-4-nitrobenzene and subsequent reduction of dinitro intermediate led to a new triphenylamine-containing aromatic diamine monomer, 4,4’-Diamino-4”-(N-pyrrolyl)triphenylamine. This newly synthesized diamine monomer was polycondensed with various aromatic dicarboxylic acids and tetracarboxylic dianhydrides to produce two series of novel triphenylamine-based polyamides and polyimides with pendent pyrrolyl substituents. Almost all the studied polymers could afford amorphous and tough films. These polymers showed high glass transition temperatures between 286 and 317 ℃, and they were stable up to a temperatue above 450℃ (for polyamides) or 500℃ (for polyimides). These polymers exhibited UV-Vis absorption maxima around 316 to 363 nm in NMP solution. The photoluminescence spectra of most of the polyamides in NMP exhibited a peak emission wavelength in the blue at 380-452 nm. The hole-transporting and electrochromic properties were examined by electrochemical and spectroelectrochemical methods. Cyclic voltammograms of the polyamides and polyimides showed a half-wave oxidation potential (E1/2) 0.88-0.94 V and 1.14-1.28 V (versus Ag/AgCl), respectively, in an acetonitrile solution. The polyamide films revealed good stability of electrochromic characteristics, with a coloration change of the film from the pale yellow neutral form to the green oxidized form. The coloration change was followed by UV-Vis spectroscopy. Advisor Committee HSIAO, Sheng-Huei - advisor
Files Date of Defense 2007-01-27 Date of Submission 2007-02-16