The solubility of fullerene as a result of a special bond

Scientists from CATRIN, IOCB and VSB-TUO described the reaction of fullerene and piperidine, in which this nanomaterial dissolves. In two studies, published by prestigious journals JACS and Angewandte Chemie, they scrutinized reactions between secondary amines (piperidine) and fullerene consisting of 60 carbon atoms on the basis of theoretical calculations as well as experiments. When the reaction occurs without oxygen, the formation of a complex with a N→C dative bond occurs, while in the presence of oxygen, the reaction continues to produce addition reaction products. The electronic structure of dative bond complexes and addition reaction products is fundamentally different. These findings can contribute to further application of this nanomaterial, for example, in energy storage.

Fullerene is the first nanomaterial discovered to open the door to nanotechnology. The discovery and study of the properties of fullerenes was awarded the Nobel Prize in Chemistry in 1996. It is one of the most widely studied materials due to its unique properties. However, its wider application is still hindered by a relatively low solubility. One of the known solvents that can be used successfully with fullerene is piperidine.

“Fullerene was known to be soluble in piperidine, but we never knew why. We have found, using theoretical calculations and experimental methods, that this is a very specific bond whose character is affected by the presence of oxygen,” said theoretical chemist from IOCB and VSB-TUO Pavel Hobza.

These findings are also very important for the application of fullerene. “As described in both articles, the results raise the possibility of controlled functionalization of one of the most well-known nanomaterials. Understanding the interaction of fullerene with organic molecules opens the door to the applicability of fullerene in energy storage facilities, for example,” said another author Radek Zbořil from CATRIN and VSB-TUO.