Synthesis and Properties of Novel Triphenylamine-based Polyimides with Adamantyl-Substituted Phenoxy Pendent Groups

• Main Authors: Chen-hua Kuo, 郭珍華
• Other Authors: Sheng-huei Hsiao
• Format: Others
• Language: en_US
• Published: 2006
• Online Access: http://ndltd.ncl.edu.tw/handle/2bs84e

碩士 === 大同大學 === 化學工程學系(所) === 95 === 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 polyimides with adamantylphenoxy-substituted triphenylamino groups were prepared from the newly synthesized diamine monomer with aromatic tetracarboxylic dianhydridess. The polyimides were amorphous and could afford transparent, tough, and flexible films with good mechanical properties. The polymers showed excellent thermal stability, with high glass transition temperatures between 273 and 310 °C, 10% weight-loss temperatures in excess of 527 °C, and char yields higher than 52% at 800 °C in nitrogen. The hole-transporting and electrochromic properties are examined by electrochemical and spectroelectrochemical methods. Cyclic voltammograms of the polyimide films on an indium-tin oxide (ITO)-coated glass substrate exhibited one pair of reversible redox couples at E1/2 = 1.12~1.13 V versus Ag/AgCl in an acetonitrile solution. The polyimide films revealed excellent stability of electrochromic characteristics by continuous several cyclic scans between 0.0 and 1.4 V; the color of the films changed from the pale yellowish neutral form to the blue oxidized form.