Effects of π-bridges on the electrochemical and electrochromic properties of bis(triarylamine)-based aramids

IF 3.9 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments Pub Date : 2026-06-01 Epub Date: 2026-01-20 DOI:10.1016/j.dyepig.2026.113585

Sheng-Huei Hsiao , Yaw-Terng Chern , Qun Zhang , Meng-Dong Lee , Nien-Chen Tsai

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Abstract

Aromatic polyamides (aramids) featuring dual triarylamine cores in the repeating unit were synthesized through phosphorylation polyamidation using 4,4′-oxydibenzoic acid and three bis(triarylamine)-diamine monomers, each with varying aromatic π-bridges, specifically 1,4-phenylene, naphthalene-2,6-diyl, and pyrene-1,6-diyl groups. These aramids demonstrated excellent solubility in polar organic solvents, enabling the formation of flexible and robust films via solution casting. They demonstrated significant thermal stability, characterized by moderate glass transition temperatures (236–262 °C), negligible weight loss below 400 °C, and high char yields (exceeding 60 % at 800 °C in nitrogen). The polymer films displayed reversible redox processes and pronounced color changes during cyclic voltammetry scanning within the range of 0–1.2 V. The structural effects of the aromatic π-bridges between the triarylamine cores on both the oxidation potential and electrochromic stability of the aramids were investigated. Notably, for aramids with greater separation between the triarylamine centers, the oxidation onset potential increased, while electrochromic stability decreased.

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π桥对双（三芳胺）基芳烃电化学和电致变色性能的影响

以4,4 ' -氧二苯甲酸和3个双（三芳胺）-二胺单体为原料，分别具有不同的芳香π桥，分别为1,4-苯基、萘-2,6-二酰基和芘-1,6-二酰基，通过磷酸化聚酰胺合成具有重复单元双三芳胺核的芳香族聚酰胺（aramids）。这些芳烃在极性有机溶剂中表现出优异的溶解度，通过溶液铸造形成灵活而坚固的薄膜。它们表现出显著的热稳定性，其特点是适度的玻璃化转变温度（236-262°C），在400°C以下的重量损失可以忽略不计，以及高炭产率（在800°C的氮气中超过60%）。在0 ~ 1.2 V的循环伏安扫描过程中，聚合物薄膜呈现出可逆的氧化还原过程和明显的颜色变化。研究了三芳胺核间芳香π桥结构对芳烃氧化电位和电致变色稳定性的影响。值得注意的是，对于三芳胺中心间距较大的芳烃，氧化电位增加，而电致变色稳定性降低。

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来源期刊

Dyes and Pigments 工程技术-材料科学：纺织

CiteScore

8.20

自引率

13.30%

发文量

933

审稿时长

33 days

期刊介绍： Dyes and Pigments covers the scientific and technical aspects of the chemistry and physics of dyes, pigments and their intermediates. Emphasis is placed on the properties of the colouring matters themselves rather than on their applications or the system in which they may be applied. Thus the journal accepts research and review papers on the synthesis of dyes, pigments and intermediates, their physical or chemical properties, e.g. spectroscopic, surface, solution or solid state characteristics, the physical aspects of their preparation, e.g. precipitation, nucleation and growth, crystal formation, liquid crystalline characteristics, their photochemical, ecological or biological properties and the relationship between colour and chemical constitution. However, papers are considered which deal with the more fundamental aspects of colourant application and of the interactions of colourants with substrates or media. The journal will interest a wide variety of workers in a range of disciplines whose work involves dyes, pigments and their intermediates, and provides a platform for investigators with common interests but diverse fields of activity such as cosmetics, reprographics, dye and pigment synthesis, medical research, polymers, etc.