含三蝶烯結構之聚(醯胺-醯亞胺)及 聚(醯胺-三芳香胺)的合成與性質研究

邱郁婷

doi:10.6841/NTUT.2012.00540

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含三蝶烯結構之聚(醯胺-醯亞胺)及聚(醯胺-三芳香胺)的合成與性質研究

Synthesis and Properties of Triptycene-containing Poly(amide-imide)s and Poly(amide- triarylamine)s

邱郁婷 , Masters　　Advisor：蕭勝輝;郭文正　　

英文 DOI： 10.6841/NTUT.2012.00540

三蝶烯；聚醯胺醯亞胺；熱性質；溶解度；電聚合；電致變色；電化學；光譜電化學； triptycene ； poly(amide-imide)s ； thermal properties ； solubility ； electropolymerization ； electrochromism ； electrochemistry ； spectroelectrochemistry

Abstract │ Reference (58) │ Altmetrics

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First, a diimide-diacid monomer bearing the triptycene unit, namely 1,4-bis(4-trimellitimidophenoxy)triptycene, was synthesized from the condensation reaction of 1,4-bis(4-aminophenoxy)triptycene and two equivalent amount of trimellitic anhydride. A series of new poly(amide-imide)s (PAIs) with triptycene units in the main chain were prepared by the phosphorylation polyamidation reactions from the diimide-diacid monomer with several aromatic diamines including commercially available diamines and 1,4-bis(4-aminophenoxy)triptycene. All the resulting PAIs were readily soluble in many organic solvents and could be solution-cast into tough and flexible polymer films. These PAIs exhibited glass-transition temperatures (Tgs) in the range of 274-305 °C, and they did not show significant weight-loss before 500 oC. In comparison with the structurally similar PAIs without the triptycene unit, the present PAIs exhibited higher solubility, lower crystallization tendency, and better film formability.
In addition, four diamide derivatives featuring a triptycene as an interior core and terminal electroactive triphenylamine (TPA) or carbazole groups were prepared by the condensation reactions from 1,4-bis(4-aminophenoxy)triptycene with 4-carboxytriphenylamine and N-(4-carboxyphenyl)carbazole, respectively, and from 1,4-bis(4-carboxyphenoxy)triptycene with 4-aminotriphenylamine and N-(4-aminophenyl)carbazole, respectively. The electrochemistry and electropolymerization of these diamide derivatives were investigated. The electrogenerated poly(amide-triarylamine) films exhibited reversible electrochemical oxidation processes and strong color changes upon electro-oxidation, which can be switched by potential modulation. The electrochromic properties of the films were evaluated by the spectroelectrochemical and electrochromic switching studies.

Reference ( 58 ) 〈TOP〉

1. (a) Mittal, K. L., Polyimides: Synthesis, Characterization and Application. Plenum: New York, 1984; (b) Wilson, D.; Stenzenberger, M. D., Polyimides. Chapman & Hall: New York, 1990; (c) Sroog, C. E., Polyimides. Prog. Polym. Sci. 1991, 16 (4), 561-694.
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3. Walsh, C. J.; Mandal, B. K., A New Class of Aromatic Dianhydrides for Thermostable Polyimides. Chem. Mater. 2001, 13, 2472-2475.
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7. Yang, J. S.; Yan, J. L., Central-ring functionalization and application of the rigid, aromatic, and H-shaped pentiptycene scaffold. Chem Commun (Camb) 2008, (13), 1501-12.
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8. Bartlett, P. D.; Ryan, M. J.; Cohen, S. G., Triptycene (9,10-o-Benzenoanthracene). J. Am. Chem. Soc. 1942, 64, 2649-2653.
連結：
9. (a) Wittig, G.; Ludwig, R., Triptycen aus anthracen und dehydrobenzol Angew. Chem. 1956, 68, 40; (b) Wittig, G., Triptycene. Org. Synth. 1959, 39, 75.
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