A type of novel triphenylamine (TPA)-based diisocyanide derivative, 4-isocyano-N-(4-isocyanophenyl)-N-(4-methoxyphenyl)aniline (M1), was successfully synthesized via Hofmann treatment of its primary amine precursor (2). A series of polyamides (P1–P3), which containing TPA units in backbones, were successfully synthesized via efficient benzoxazine-isocyanide-chemistry (BIC) at room temperature by using M1 and bifunctional benzoxazines as starting monomers. Chemical structures of P1–P3 were verified by FT-IR, ¹H NMR and gel permeation chromatography (GPC) analyses. Polymers’ films were prepared by solution coating (using DMSO as solvent), and electrochemical properties of P1–P3 were investigated by cyclic voltammetry (CV). P1–P3 exhibited single-step highly reversible oxidation process, reflecting their good electrochemical activity. Electrochromic properties of polymers were further analyzed by spectroelectrochemical techniques. New absorption bands at ∼750 nm appeared in UV–vis spectra of P1–P3 when the applied voltage reached ∼0.65 V, accompanied by the obvious visual color change (from colorless to blue-green). Response time and coloration efficiency of P1–P3 were also investigated here. The work carried out in this study proved that BIC can act as powerful tool to construct novel functional polyamides.

通过霍夫曼对其伯胺前体进行处理，成功合成了一种新型的基于三苯胺（TPA）的二异氰酸酯衍生物-4-异氰基-N-（4-异氰基苯基）-N-（4-甲氧基苯基）苯胺（M1）（2）。在室温下，以M1和双官能苯并恶嗪为起始单体，通过有效的苯并恶嗪-异氰化物化学（BIC）成功地合成了一系列在主链中包含TPA单元的聚酰胺（P1-P3）。P1–P3的化学结构已通过FT-IR验证，¹1 H NMR和凝胶渗透色谱法（GPC）分析。通过溶液涂布（使用DMSO作为溶剂）制备聚合物薄膜，并通过循环伏安法（CV）研究P1-P3的电化学性能。P1-P3表现出单步高度可逆的氧化过程，反映出它们良好的电化学活性。聚合物的电致变色性质通过光谱电化学技术进一步分析。当施加的电压达到〜0.65 V时，P1-P3的UV-vis光谱在〜750 nm处出现新的吸收带，并伴随着明显的视觉颜色变化（从无色变为蓝绿色）。P1-P3的响应时间和显色效率在这里也进行了调查。这项研究进行的工作证明BIC可以作为构建新型功能聚酰胺的有力工具。