有机化学 ›› 2014, Vol. 34 ›› Issue (4): 804-808.DOI: 10.6023/cjoc201308040 上一篇    下一篇

研究论文

含肉桂酸酯基螺噁嗪的合成及性质研究

杨素华a, 闫素君b, 郇玲a   

  1. a 赤峰学院化学化工学院 赤峰 024000;
    b 中山大学化学化工学院 广州 510275
  • 收稿日期:2013-08-31 修回日期:2013-11-10 出版日期:2014-04-25 发布日期:2013-12-06
  • 通讯作者: 杨素华 E-mail:cfyangsuhua@126.com
  • 基金资助:

    内蒙古自治区高等学校科学研究基金(No. NJ10244)资助项目

Synthesis and Properties of a Novel Spirooxazine Dye

Yang Suhuaa, Yan Sujunb, Huan Linga   

  1. a School of Chemistry and Chemical Engineering, Chifeng College, Chifeng 024000;
    b School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275
  • Received:2013-08-31 Revised:2013-11-10 Online:2014-04-25 Published:2013-12-06
  • Supported by:

    Project supported by the Research Program of Science at Universities of Inner Mongolia Autonomous Region (No. NJ10244).

通过缩合法合成了含有肉桂酸酯基的双功能螺噁嗪类化合物,用红外光谱、核磁共振氢谱、碳谱和X射线单晶衍射对其结构进行了表征. 紫外-可见光谱研究结果表明:当用400 W高压汞灯照射后化合物在有机溶剂以及高分子膜中都表现出了很好的可逆光致变色性. 化合物也显示出了酸致变色性能. 此外着重研究了化合物酸致变色荧光性能以及在150 W氙灯照射前后的荧光光谱. 加入酸后和光照前后荧光光谱的改变使其有望作为荧光分子开关、非破坏性数据的读取存储介质材料.

关键词: 螺噁嗪, 光致变色, 肉桂酸, 酸致变色, 荧光

A novel bifunctional photochromic compound 2 based on spirooxazine and cinnamoyl moiety was synthesized by esterification reaction. Its structure was characterized by 1H NMR, 13C NMR, IR and X-ray single crystal diffraction. The compound was proved by UV testing to have excellent photochromic properties both in organic solvents and polymer films when irridiated with high pressure Hg lamp. The acidichromism phenomenon of compound 2 was studied too. No significant fluorescence emission of compound 2 was observed in EtOH solution before and after irradiation. Under the acidic condition or irradiation with 150 W Xe lamp, The ethanol solution of compound 2 exhibits a good fluorescence respectively. The ethanol solution of compound 2 exhibits obvious fluorescence emission. After irradiating the acidic solution, new fluorescence emission can be observed. The emission change modulated by acid or light offers compound 2 to be potential as a new fluorescent molecular switch.

Key words: spirooxazine, photochromism, cinnamate, acidichromism, fluorescence