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Title page for etd-0205107-194047


URN etd-0205107-194047 Statistics This thesis had been viewed 2764 times. Download 739 times.
Author Chia-Sheng Chiang
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 72
Title Synthesis, Electrochemistry and Photoluminescence of High-Performance Polymers Bearing Pyrrole-substituted Triphenylamino Groups
Keyword
  • Triphenylamine
  • Pyrrole
  • Photoluminescence
  • Polyamide
  • Polyamide
  • Photoluminescence
  • Pyrrole
  • Triphenylamine
  • Abstract This thesis consists of two parts. The first part describes the synthesis and properties of novel aromatic poly(amine-amide)s containing 4-(N-pyrrolyl)triphenylamine moieties. A new pyrrole-derived triphenylamine-containing dicarboxylic acid monomer, 4,4'-dicarboxy-4"-(N-pyrrolyl)triphenylamine, was synthesized via the aromatic nucleophilic fluoro-displacement reaction of 4-fluorobenzonitrile with 4-(N-pyrrolyl)aniline using sodium hydride as the base, followed by alkaline hydrolysis of the dinitrile intermediate. One series of poly(amine-amide)s with inherent viscosities of 0.52-0.88 dL/g were prepared by the direct phosphorylation polycondensation from the synthesized diacid monomer with various aromatic diamines. The resultant poly(amine-amide)s were readily soluble in a variety of organic solvents and could afford strong and tough films via solution casting. These aromatic poly(amine-amide)s have useful levels of thermal stability associated with high glass transtion temperatures (Tg=275-326 ℃) and 10 % weight loss temperatures in excess of 450 ℃ in nitrogen. In dilute NMP solution, these polymers exhibited a medium to strong photoluminescence in the blue region at 446~455 nm with quantum yield up to 38 %.
    The second part of this thesis investigates the synthesis and properties of novel poly(amine-hydrazide)s and poly(amine-1,3,4-oxadiazole)s containing pyrrolyl-substituted triphenylamine units. Two novel poly(amine-hydrazide)s were synthesized from 4,4'-dicarboxy-4"-(N-pyrrolyl)triphenylamine with terephthalic dihydrazide (TPH) and isophthalic dihydrazide (IPH) via the Yamazaki phosphorylation reation. The obtained poly(amine-hydrazide)s were easily soluble in polar organic solvents such as N-methyl-2-pyrrolidone (NMP) and N,N-dimethylacetamide (DMAc) and could be solution-cast into free-standing or strong films. The poly(amine-hydrazide) derived from IPH exhibited strong blue photoluminescence at 478 nm in NMP with 33 % quantum yield. Differential scanning calorimetry (DSC) indicated that these two hydrazide polymers had Tg values of 252℃ (from TPH) and 235℃ (from IPH), respectively, and could be thermally cyclodehydrated into the corresponding oxadiazole polymers in the range of 300-400℃. The resulting poly(amine-1,3,4-oxadiazole)s exhibited Tg around 266-268℃, 10 % weight-loss temperature in excess of 543℃, and char yield at 800℃ in nitrogen higher than 70 %. In comparison with the parent triphenylamine-based analogs without the pyrrole pendent group, the newly synthesized poly(amine-amide)s and poly(amine-hydrazide)s containing the 4-(N-pyrrolyl)triphenylamine unit revealed a relatively decreased electrochemical stability.
    Advisor Committee
  • Sheng-Huei Hsiao - advisor
  • Guey-Sheng Liou - co-chair
  • Wen-Fu Lee - co-chair
  • Files indicate access worldwide
    Date of Defense 2007-01-26 Date of Submission 2007-02-05


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