摘要
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40mV,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．
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.
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
2006年第11期1557-1561,共5页
Chinese Journal of Organic Chemistry
基金
高等学校博士学科点专项科研基金(No.20030007011)
北京理工大学基础研究基金(No.000Y06)资助项目.
关键词
单加成环丙烷富勒烯膦酸衍生物
合成
电化学性能
循环伏安法
mono-methano[60]fullerene organophosphonate
synthesis
electrochemical property
cyclic voltammetry
