2,4,2'-三羟基偶氮苯的合成及掺杂薄膜的光致异构性能

Synthesis and Photoisomerization of Film Containing 2,4,2'-Trihydroxyazobenzene

以2-氨基苯酚和间苯二酚为原料,通过重氮偶合反应合成了2,4,2'-三羟基偶氮苯,并利用红外光谱、核磁分析、电喷雾电离质谱和元素分析对其进行了系统的结构表征;通过主客体物理掺杂方法制备了2,4,2'-三羟基偶氮苯-聚甲基丙烯酸甲酯(PMMA)薄膜;利用紫外-可见吸收光谱分别考察了目标化合物在四氢呋喃(THF)溶液、PMMA薄膜中的光致异构性能,及其在不同极性有机溶剂中异构化的动力学反应。研究结果表明,经365 nm紫外光激发,目标化合物无论在溶剂中还是在聚合物薄膜中都表现出良好的反-顺异构化响应,异构化产率非常高,产物光、热稳定性好,异构反应为一级动力学反应,异构速率常数随着有机溶剂极性增大而减小。

Starting from 2-aminophenol and resorcinol,2,4,2'-trihydroxy azobenzene was synthesized via diazo and coupling reaction,and its structure was determined by FT-IR,1H-NMR,13C-NMR,electrospray ionization mass spectrometry( ESI-MS) and element analysis. Then polymethyl methacrylate( PMMA) film doped with 2,4,2'-trihydroxy azobenzene was produced by physical method. The photoisomerization properties in tetrahydrofuran( THF) and polymethyl methacrylate were studied by UV-vis spectrum,plus kinetics in different organic solvents. The results show that the title compound displays significant photoisomerization in THF and PMMA irradiated by UV light( λ = 365 nm). The cisisomer product has a high yield,excellent thermostability and photostability. The tran-cis isomerization is a first-order reaction. Isomerization speed constant values decrease with increasing polarity of the organic solvents.