Structure of 7,9,12,15,18,20,39,24,45,57-C60(CF3)10(1,2:3,4-O)2. The first regiospecific diepoxidation of a fullerene derivative.
Structure of 7,9,12,15,18,20,39,24,45,57-C60(CF3)10(1,2:3,4-O)2. The first regiospecific diepoxidation of a fullerene derivative.
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DOI：
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发表时间：
2013-11
影响因子：
1.2
通讯作者：
James B. Whitaker;N. Shustova;S. Strauss;B. V
中科院分区：
文献类型：
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作者：
James B. Whitaker;N. Shustova;S. Strauss;B. V
人们发现，当暴露在空气中时，C60(CF3)10 异构体在溶液中会缓慢发生不寻常的区域特异性双环氧化反应。这是全氟烷基富勒烯在环境条件下进行环氧化的唯一已知例子。该化合物通过多种分析方法进行了表征，包括 19F NMR 光谱、APCI-MS、紫外可见光谱和 X 射线晶体学。人们探索了许多氧化方法，包括臭氧化、光解、热解和间氯过氧苯甲酸的化学氧化，但没有一种方法产生双环氧化合物。这表明该过程在动力学上非常缓慢，可能是由于氧加成位点周围的空间拥挤所致。随着越来越多的富勒烯和富勒烯衍生物被用于有机电子器件，这些原本稳定的化合物自发双环氧化的发现具有深远的影响，并且它们在环境条件下对氧化的不稳定性可能会改变器件的性能。
An unusual regiospecific diepoxidation of an isomer of C60(CF3)10 was discovered to slowly occur in solution while exposed to air. This is the only known example of a perfluoroalkyl fullerene undergoing epoxidation under ambient conditions. This compound was characterized by a variety of analytical methods including 19F NMR spectroscopy, APCI-MS, UV-vis spectroscopy, and X-ray crystallography. Numerous oxidation methods were explored including ozonation, photolysis, thermolysis, and the chemical oxidation by m-chloroperoxobenzoic acid, none of which has yielded the diepoxide. This indicated that the process is kinetically very slow, presumably due to steric crowding around the oxygen addition sites. These findings of spontaneous diepoxidation of the otherwise stable compound have far reaching implications as more fullerenes and fullerene derivatives are being used in organic electronics, and their instability toward oxidation in ambient conditions may alter the performance of the device.