有机化学 ›› 2015, Vol. 35 ›› Issue (5): 1131-1136.DOI: 10.6023/cjoc201412002 上一篇    下一篇

研究简报

二茂铁查尔酮衍生物的电化学与热性质

王栋, 朱学友, 赵海英, 边占喜   

  1. 内蒙古自治区精细有机合成重点实验室 内蒙古大学化学化工学院 呼和浩特 010021
  • 收稿日期:2014-12-01 修回日期:2014-12-26 发布日期:2014-01-14
  • 通讯作者: 赵海英 E-mail:hyzhao@imu.edu.cn
  • 基金资助:

    国家自然科学基金(No.21102068)、内蒙古自治区高等学校科学研究(No.NJZZ001)和内蒙古自治区自然科学基金(Nos.2013MS0207,2014JQ02)资助项目.

Electrochemical and Thermal Properties of Ferrocene-Containing Chalcone Derivatives

Wang Dong, Zhu Xueyou, Zhao Haiying, Bian Zhanxi   

  1. Inner Mongolia Key Laboratory of Fine Organic Synthesis and College of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot 010021
  • Received:2014-12-01 Revised:2014-12-26 Published:2014-01-14
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No.21102068), the Research Program of Science and Technology at Universities of Inner Mongolia (No.NJZZ001) and the Natural Science Foundation of Inner Mongolia (Nos.2013MS0207, 2014JQ02).

合成并表征了含有苯环(3a~3d)和萘环(3e~3h)的两系列二茂铁查尔酮衍生物. 这些化合物具有较好的紫外可见吸收性质. 循环伏安实验中代表化合物3b3f均展示可逆的单电子氧化还原进程, 且萘环取代苯环对二茂铁的氧化还原性质未产生影响. 与二茂铁相比, 二茂铁查尔酮衍生物难失去电子, 稳定性增加. 热性质研究表明, 两系列化合物均在250~260 ℃左右开始降解, 对于同一系列化合物3a~3d3e~3h, 随着烷基链的增加, 熔点都出现下降趋势. 当分子刚性部分以苯环为主时, 随着烷基链的加长, 第一次升温中发生了不稳定的多晶相转变; 当分子含有萘环时, 分子熔点升高, 此时延长烷基链对晶相的稳定性影响不大. 这些研究为此类化合物在功能材料方面的应用提供一定的理论依据.

关键词: 二茂铁, 查尔酮, 电化学, 热性质

Ferrocene-containing chalcone derivatives with benzene rings (3a~3d) or naphthalene rings (3e~3h) were synthesized and characterized. These compounds exhibited good UV-vis absorption properties. The cyclic voltammogram investigations revealed that redox-active ferrocenyl groups of 3b and 3f exhibited one-electron transfer processes and naphthalene rings instead of benzene rings had little or no effect on the formal redox potential of ferrocene. As compared to the ferrocene standard, it was difficult to lost electron for ferrocene-containing chalcone derivatives indicating their high stability. Their thermal behaviors indicated that these compounds started to decompose at about 250~260 ℃, and the melting points decreased with lengthening terminal alkyl chains. When the rigid core of molecular were mostly benzene rings, crystal polymorphic phase transitions with lengthening terminal alkyl chains was observed in the first heating cycle; whereas the melting points increased when the rigid core of molecular contained naphthalene rings, and lengthening terminal alkyl chains had little effect on the crystal phase stability. The research is supposed to provide some theoretical basis for this kind of compound using in function materials.

Key words: ferrocene, chalcone, electrochemistry, thermal behavior