Synthesis of pendant fullerene dimers by an aminomethylation reaction of fulleropyrrolidines bearing ketone moieties,Organic & Biomolecular Chemistry

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Synthesis of pendant fullerene dimers by an aminomethylation reaction of fulleropyrrolidines bearing ketone moieties
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2023-05-22 , DOI: 10.1039/d3ob00365e
Qian-Na Peng ₁ , Hui-Juan Wang ₂ , Xing-Yu Wang ₁ , Fa-Bao Li ₁ , Li Liu ₁ , Xiaoli Wang ₃ , Ping Wu ₃ , Chao-Yang Liu ₂

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An aminomethylation reaction of fulleropyrrolidines bearing ketone moieties in the presence of N-unsubstituted fulleropyrrolidines and paraformaldehyde with the aid of p-toluenesulfonic acid afforded a series of scarce pendant fullerene dimers. A simple change of reaction substrates from ketone to ketone-containing fulleropyrrolidines successfully realized the synthesis of a variety of novel pendant fullerene dimers, including those from methyl ketone-containing fulleropyrrolidines, which were considered to produce the known bridged fullerene dimers. It should be noted that pendant fullerene dimers are usually difficult to prepare by other methods and may have promising applications in perovskite solar cells. Density functional theory (DFT) has been employed to elucidate the regioselectivity of methyl ketone-containing fulleropyrrolidines to yield exclusively pendant fullerene dimers by investigating the Gibbs free energy profile of the reaction starting from methyl ketone-containing fulleropyrrolidines and iminium intermediates.

中文翻译：

带酮部分的富勒烯吡咯烷氨甲基化反应合成悬垂富勒烯二聚体

在N-未取代的富勒罗吡咯烷和多聚甲醛的存在下，在p的帮助下，带有酮部分的富勒罗吡咯烷的氨基甲基化反应-甲苯磺酸提供了一系列稀有的悬垂富勒烯二聚体。反应底物从酮到含酮的富勒烯吡咯烷的简单变化成功地实现了多种新型悬垂富勒烯二聚体的合成，包括来自含甲基酮的富勒烯吡咯烷的那些，它们被认为可以产生已知的桥联富勒烯二聚体。应该注意的是，悬垂的富勒烯二聚体通常很难通过其他方法制备，并且可能在钙钛矿太阳能电池中具有广阔的应用前景。

更新日期：2023-05-22

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