X-ray photoemission spectroscopy study on the effects of functionalization in fulleropyrrolidine and pyrrolidine derivatives

Fulleropyrrolidine and pyrrolidine derivatives were studied using X-ray photoemission spectroscopy in order to determine the effects of the C(60)-cage on the pyrrolidine nitrogen, as well as the influence of further derivatisation. Charge transfer from the carbon pyrrolidine ring to the C(60)-cages is observed and this charge redistribution influences not only the carbon atoms but also the nitrogen. The major influence of different functionalization groups on the pyrrolidine nitrogen is whether or not they lead to quaternisation while no differences could be detected for different groups (methyl group or alkyl chain) producing one or the other configuration. However, the type of counter ion is important for the stability of the pyrrolidinium nitrogen: demethylated nitrogen, always found to be present in iodide counter balanced compounds, disappears in compounds counter balanced with BF(4)(-) anion. (c) 2006 Elsevier Ltd. All rights reserved