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化学学报
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化学学报 ›› 2010, Vol. 68 ›› Issue (18): 1895-1902. 上一篇    下一篇

研究论文

新型含氮杂环螺吡喃化合物的合成及性能研究

庞美丽*，杨涛涛，李晶晶，杨素华，娄志刚，韩杰，孟继本*   

  1. (南开大学化学系 天津 300071)
  • 投稿日期:2010-01-04 修回日期:2010-04-18 发布日期:2010-05-17
  • 通讯作者: 孟继本 E-mail:mengjiben@nankai.edu.cn
  • 基金资助:

    国家自然科学基金项目;国家自然科学基金项目

Synthesis and Properties of Novel Photochromic Spiropyran Compounds with N-heterocyclic Residue

(Department of Chemistry, Nankai University, Tianjin 300071)   

  • Received:2010-01-04 Revised:2010-04-18 Published:2010-05-17

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1863

被引次数

61 | 2

为了改善螺吡喃的光致变色性能, 提高这一系列化合物的耐疲劳度, 在螺吡喃吲哚啉环的氮原子上通过短碳链引入含氮杂环基团, 成功合成了1 -(3-N-杂环基丙基)-3 ,3 -二甲基-6-硝基螺[吲哚啉-2,2 (2H)苯并吡喃] (4a～4f). 这一系列新的化合物. 用核磁共振氢谱、碳谱、红外光谱和元素分析对这些化合物进行结构表征. 通过紫外吸收光谱研究化合物在不同溶液(乙醇、二氯甲烷和环己烷)中和不同高分子膜(PMMA和PVB)中的变色性质. 进一步对化合物4a在不同溶液中的动力学性质, 以及在PMMA膜和PVB膜中的热消色动力学性质进行了研究, 拟合计算并比较了消色过程的动力学常数. 最后, 又将化合物4a和不含含氮杂环的螺吡喃母体进行比较, 发现耐疲劳度有很大提高.

关键词: 光致变色, 螺吡喃, 热消色, 动力学, 耐疲劳度

In order to improve the photochromic properties and the fatigue resistance of spiropyran, nitrogen-containing heterocycles were introduced into the indolino ring of the spiropyran through the short carbon chain linkage leading to the synthesis of novel spiropyran compound 1 -(3-N-heterocyc- licpropyl)-3 ,3 -dimethyl-6-nitrospiro[indoline-2,2 (2H)benzopyran] (4a～4f). All compound 4a～4f were characterized by 1H NMR, 13C NMR, IR, and elemental analysis. The photochromic properties of compounds 4a～4f in different solution (ethanol, dichloromathane, and cyclohexane) and polymer film (PMMA and PVB) were studied with the aid of UV absorption spectrometry. The thermal decay process of the representative compound 4a in different solution and polymer film were recorded and analyzed, and the kinetic process were fitted and discussed according to the first-order and second-order kinetics equation. Finally, in comparision with parent spiropyran compound without nitrogen-containing heterocyclic residue, compound 4a possess the better fatigue resistance.

Key words: photochromism, spiropyran, thermal decay, kinetics, fatigue resistance