SYNTHESIS OF A FULLERENE[60] CRYPTATE AND SYSTEMATIC LANGMUIR-BLODGETT AND THIN-FILM INVESTIGATIONS OF AMPHIPHILIC FULLERENE DERIVATIVES

The synthesis of the first fullerene cryptate 7 with a sodium ion bound to a benzo[2.2.2]cryptand covalently attached to a methanofullerene[60] is described. The amphiphilic properties of 7 as well as of a variety of other covalent fullerene derivatives with polar functional groups and the ability of these compounds to form Langmuir monolayers at the air-water interface were investigated in a systematic study. Among these derivatives are Diels-Alder adducts of C-60 and methanofullerenes, four of which are fullerene C-glycosides. The films at the water surface were characterized by their surface pressure versus molecular area isotherms, compression and expansion cycles, and optical light microscopy. UV/Vis spectroscopy and small-angle X-ray diffraction (SAXS) were employed for LB film characterization on solid substrates. Parameters influencing the spreading and monolayer character include a) polarity, b) balance of hydrophobicity to hydrophilicity, c) size and bulkiness of the polar groups attached to the fullerene, and d) presence of aromatic residues in these groups.