| Summary: | 碩士 === 國立臺北科技大學 === 化學工程研究所 === 100 === 4-Nitro-N-(4-nitrophenyl)-N-(4-(5-(p-tolyl)-1,3,4-oxadiazol-2-yl)phenyl)aniline were synthesized via the cesium fluoride-mediated N-arylation reactions of 4-(5-(p-tolyl)-1,3,4-oxadiazol-2-yl)aniline with 1-fluoro-4-nitrobenzene, followed by oxidation reaction by potassium permanganate. Further palladium-catalyzed hydrazine reduction led to a new triphenylamine-based AB2 type monomer containing a carboxylic acid and two amino groups. The self-polycondensation of the AB2 monomer (6) afforded hyperbranched poly(triphenylamine-1,3,4-oxadiazole amide)s with amino end groups. The numerous amino end groups of the hyperbranched polyamide were modified by endcapping with acetyl chloride, benzoyl chloride, 4-nitrobenzoyl chloride,pentanoyl chloride and 1-(4-methoxyphenyl)ethanone.
The structures of hyperbranched polymers were confirmed by FT-IR and NMR. The optical properties were analyzed by UV-Vis and PL spectroscopy. The thermal properties were measured by TGA and DSC. The hyperbranched polyamide exhibited UV-Vis absorption band at 264~284 nm and 372~384nm and showed PL maxium emission peaks at 434~560nm in NMP solution. The glass-transition temperatures were not discernible and 5％ weight loss temperature was 344~455℃ under nitrogen. The inherent viscosity of the polymer were 0.09~0.14 dL/g. The electrochemical properties of the hyperbranched polyamide were investigated by cyclic voltammetry. The energy levels of the HOMO and the LUMO wewe respectively estimated as -5.34~ -5.2 eV and -2.82~ -2.73 eV from the oxidation potential and the onset absorption wavelength of the UV-vis spectra.
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