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有机化学
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有机化学 ›› 2005, Vol. 25 ›› Issue (05): 570-575. 上一篇    下一篇

研究论文

新型四硫富瓦烯硫杂冠醚衍生物的合成

陈铁，刘武军，丛志奇，尹炳柱*   

  1. (延边大学理工学院化学系 延吉 133002)
  • 收稿日期:2004-09-27 修回日期:2004-12-06 发布日期:2004-04-30
  • 通讯作者: 尹炳柱

Synthesis of Novel Dithia-crown Ether Annulated Tetrathiafulvalene Derivatives

CHEN Tie,LIU Wu-Jun,CONG Zhi-Qi,YIN Bing-Zhu*   

  1. (Department of Chemistry, School of Science and Engineering, Yanbian University, Yanji 133002)
  • Received:2004-09-27 Revised:2004-12-06 Published:2004-04-30
  • Contact: YIN Bing-Zhu

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1271

被引次数

45

在高度稀释条件下, 经4,5-二溴甲基-1,3-二硫杂环戊烯-2-硫酮(7)和多缩乙二醇的1,ω-二巯基衍生物的缩合反应, 方便地合成了4,5-位带二硫杂冠醚残基的2-硫代-1,3-二硫杂环戊烯的衍生物8a～8d, 中间体硫杂冠醚8c～8d的合成中有明显的“模板效应”. 在亚磷酸三乙酯存在下, 8a～8d经自偶联生成新型的对称双臂四硫富瓦烯(TTF)硫杂冠醚衍生物10a～10d, 而与4,5-二甲硫基-1,3-二硫杂环戊烯-2-酮(9)经交叉偶联生成新型的非对称单臂四硫富瓦烯硫杂冠醚衍生物11a～11d. 用循环伏安法研究了上述目标化合物的电化学性质和离子传感性质.

关键词: 四硫富瓦烯, 离子传感, 冠醚, 循环伏安法, 模板效应

In this paper, a series of 4,5-dithiacrown ether annulated 1,3-dithiole-2-thiones 8a～8d were prepared via condensing 4,5-bis(bromomethyl)-1,3-dithiole-2-thione (7) with 1,ω-dimercapto polyglycol derivatives in high dilution. The obvious template effect was found during the synthesis of 8c～8d. Self-coupling of crown-ether derivatives 8a～8d afforded the symmetric bis-crown-ether TTF derivatives 10a～10d and cross-coupling with 4,5-dimethylthio-1,3-dithiole-2-one (9) gave asymmetric mono crown-ether TTF derivatives 11a～11d in net triethyl phosphite. The electrochemical and ion-sensing properties of crown-ether TTF derivatives were studied by means of cyclic voltammetry.

Key words: tetrathiafulvalene, template effect, ion sensor, cyclic voltammetry, crown ether