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URN etd-1028105-133447 Statistics This thesis had been viewed 2937 times. Download 1221 times. Author Hung-yin Pan Author's Email Address No Public. Department Chemical Engineering Year 2004 Semester 2 Degree Master Type of Document Master's Thesis Language English Page Count 50 Title Synthesis, Photoluminescene and Electrochromic Properties of Novel Triphenylamine-based Polyamides with Adamantyl-Substituted Phenoxy Pendent Groups Keyword triphenylamine photoluminescene electrochromic Adamantyl-Substituted Adamantyl-Substituted electrochromic photoluminescene triphenylamine Abstract A new triphenylamine-containing aromatic diamine monomer, 4-[4-(1-adamantyl)phenoxy]-4’,4”-diaminotriphenylamine, was synthesized from cesium fluoride-mediated N-arylation of 4-(1-adamantyl)-4’-aminodiphenyl ether with 1-fluoro-4-nitrobenzene and subsequent reduction of the dinitro intermediate. A series of novel aromatic polyamides with adamantylphenoxy-substituted triphenylamino groups were prepared by the phosphorylation polyamidation of the newly synthesized diamine monomer with aromatic dicarboxylic acids. The polyamides were amorphous and soluble in polar aprotic solvents such as N-methyl-2-pyrrolidone (NMP), N,N-dimethylacetamide (DMAc), and N,N-dimethylformamide (DMF). These polymers can be solution-cast into transparent, tough, and flexible films with good mechanical properties. The polymers showed excellent thermal stability, with high glass transition temperatures between 254 and 293 °C, 10% weight-loss temperatures in excess of 493 °C, and char yields higher than 56% at 800 °C in nitrogen. These polymers exhibited strong UV-vis absorption bands at 306–357 nm in DMAc solutions. The photoluminescence spectra showed maximum bands around 430-443 nm in the blue region. The hole-transporting and electrochromic properties are examined by electrochemical and spectroelectrochemical methods. Cyclic voltammograms of the polyamide films on an indium-tin oxide (ITO)-coated glass substrate exhibited one pair of reversible redox couples at E1/2 = 0.81~0.85 V versus Ag/AgCl in an acetonitrile solution. The polyamide films revealed excellent stability of electrochromic characteristics by continuous several cyclic scans between 0.0 and 1.0 V; the color of the films changed from the pale yellowish neutral form to the green oxidized form. Advisor Committee Sheng-Huei Hsiao - advisor
Guey-Sheng Liou - co-chair
Wen-Jeng Guo - co-chair
Files Date of Defense 2005-07-29 Date of Submission 2005-10-28