具有電子授受基團結構之芳香族高分歧聚醯胺合成與性質研究

王鼎傑

doi:10.6841/NTUT.2012.00069

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具有電子授受基團結構之芳香族高分歧聚醯胺合成與性質研究

Synthesis and Properties of Hyperbranched Aromatic Polyamides Containing Donor and Acceptor Groups

王鼎傑 , Masters　　Advisor：汪昆立　　

繁體中文 DOI： 10.6841/NTUT.2012.00069

高分歧化聚醯胺；三苯胺； 1,3,4-噁二唑； Hyperbranched ； Polyamide ； Triphenylamine ； 1,3,4-oxadiazole

Abstract │ Reference (69) │ Altmetrics

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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.

Reference ( 69 ) 〈TOP〉

1 Zhou, Z.-H.; Zhou, P.-L.; Yang, S.-P.; Yu, X.-B.; Yang, L.-Z. Controllable synthesis of hydroxyapatite nanocrystals via a dendrimer-assisted hydrothermal process.Materials Research Bulletin 2007, 42, 1611-1618.
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連結：
4 Qin, H.; Mather, P. T.; Baek, J.-B.; Tan, L.-S. Modification of bisphenol-A based bismaleimide resin (BPA-BMI) with an allyl-terminated hyperbranched polyimide (AT-PAEKI).Polymer 2006, 47, 2813-2821.
連結：
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