Synthesis and electro-optical properties of aromatic polyamides and polyimides bearing pendent 3,6-dimethoxycarbazole units

[Display omitted] •A new diamine monomer with pendent 3,6-dimethoxycarbazole group was synthesized.•New electroactive polyamides and polyimides were prepared.•The polymers exhibited enhanced electrochemical and electrochromic stability.•The polymers are potential anodically coloring electrochromes....

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Bibliographic Details
Published in:European polymer journal 2015-12, Vol.73, p.50-64
Main Authors: Hsiao, Sheng-Huei, Peng, Siao-Chi, Kung, Yu-Ruei, Leu, Chyi-Ming, Lee, Tzong-Ming
Format: Article
Language:English
Subjects:
Aromatic polyamides
Carbazole
Carbazoles
Diamines
Electrochemistry
Electrochromism
Monomers
Phosphorylation
Polyamide resins
Polyamides
Polyimide resins
Polyimides
Synthesis
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Summary:[Display omitted] •A new diamine monomer with pendent 3,6-dimethoxycarbazole group was synthesized.•New electroactive polyamides and polyimides were prepared.•The polymers exhibited enhanced electrochemical and electrochromic stability.•The polymers are potential anodically coloring electrochromes. This work deals with the synthesis and characterization of a new m-phenylenediamine-type monomer with pendent 3,6-dimethoxycarbazole group, namely N-(4-(3,6-dimethoxycarbazol-9-yl)phenyl)-3,5-diaminobenzamide (2), and its derived aromatic polyamides and polyimides. New electroactive aromatic polyamides were synthesized from diamine 2 with four aromatic dicarboxylic acids via the phosphorylation polyamidation technique, and the polyimides were prepared from equimolar mixtures of 4,4′-oxydianiline and diamine 2 with four aromatic tetracarboxylic dianhydrides via a conventional two-step procedure. All the polyamides and the 6FDA-derived polyimide were readily soluble in many organic solvents and could afford strong and flexible films by solution casting. The polymers showed useful levels of thermal stability with glass-transition temperatures (Tgs) in the range of 237–313°C and 10% weight-loss temperatures in excess of 450°C. All the polyamides and polyimides showed reversible electrochemical oxidation, accompanied by strong color changes. By incorporation of electron-donating methoxy groups on the electrochemically active C-3 and C-6 sites of the carbazole unit, the polymers exhibit greatly enhanced electrochemical stability and electrochromic performance in comparison with the analogs without any substituents on the carbazole unit.
ISSN:0014-3057
1873-1945
DOI:10.1016/j.eurpolymj.2015.10.004