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有机化学
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有机化学 ›› 2006, Vol. 26 ›› Issue (11): 1557-1561. 上一篇    下一篇

研究论文

单加成环丙烷富勒烯膦酸酯衍生物的合成与电化学性能

杨新林*,a，乔新歌a，朱张广a，程福永b，朱鹤孙b，范楼珍c   

  1. (a北京理工大学生命科学与技术学院 北京 100081)
    (b北京理工大学材料科学研究中心 北京 100081)
    (c北京师范大学化学系 北京 100875)
  • 收稿日期:2005-10-24 修回日期:1900-01-01 发布日期:2006-10-27
  • 通讯作者: 杨新林

Synthesis and Electrochemical Properties of Mono- methano[60]fullerene Organophosphonates

YANG Xin-Lin*,a,QIAO Xin-Gea,ZHU Zhang-Guanga,CHENG Fu-Yongb
ZHU He-Sunb,FAN Lou-Zhenc   

  1. (a School of Life Science and Technology, Beijing Institute of Technology, Beijing 10081)
    (b Research Center of Materials Science, Beijing Institute of Technology, Beijing 100081)
    (c Department of Chemistry, Beijing Normal University, Beijing 100875)
  • Received:2005-10-24 Revised:1900-01-01 Published:2006-10-27
  • Contact: YANG Xin-Lin

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908

被引次数

7 | 1

在Mn(OAc)3•2H2O催化下, C60分别和亚甲基二膦酸四乙酯、氰基亚甲基膦酸二乙酯或乙氧羰基亚甲基膦酸二乙酯在氯苯中回流, 生成3个单加成环丙烷富勒烯膦酸衍生物C60C(R)PO(OEt)2 [1, R＝PO(OEt)2; 2, R＝COOEt; 3, R＝CN]. 与以前报道的Bingel反应法相比, 该方法副产物少并且缩短了反应时间. 采用循环伏安法发现1, 2的还原电位相对于C60发生负移, 而3的还原电位相对于C60却正移40 mV, 表明引入象氰基一样具有很强吸电子能力的取代基团, 可以改善富勒烯球的电化学性能, 合成电子接受能力较强的富勒烯衍生物.

关键词: 合成, 电化学性能, 循环伏安法, 单加成环丙烷富勒烯膦酸衍生物

In the presence of manganese(III) acetate dihydrate [Mn(OAc)3•2H2O], the reaction of [60]fullerene with tetraethyl methylenediphosphonate, diethyl cyanomethylphosphonate or diethylphosphonoacetic acid ethyl ester in refluxing chlorobenzene afforded the corresponding methano[60]fullerene organophosphonates C60C(R)PO(OEt)2 [1, R＝PO(OEt)2; 2, R＝COOEt; 3, R＝CN], respectively. This reaction produced fewer by-products and needed less reaction time. Therefore it is superior to the Bingel reaction for the preparation of compounds 1, 2 and 3. In addition, compared with C60, compounds 1 and 2 had negative shifts but 3 had a posive shift of 40 mV in reduction half-wave potentials (E1/2) determined by cyclic voltammetry. These data indicate that the introduction of electro-attracting groups such as cyano-group to fullerene ball might improve the electrochemical properties and synthesize fullerene derivatives with strong electron-accepting ability.

Key words: synthesis, electrochemical property, cyclic voltammetry, mono-methano[60]fullerene organophosphonate