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 boun d 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 vari ety of other covalent fullerene derivatives with polar functional grou ps and the ability of these compounds to form Langmuir monolayers at t he air-water interface were investigated in a systematic study. Among these derivatives are Diels-Alder adducts of C-60 and methanofullerene s, four of which are fullerene C-glycosides. The films at the water su rface were characterized by their surface pressure versus molecular ar ea isotherms, compression and expansion cycles, and optical light micr oscopy. UV/Vis spectroscopy and small-angle X-ray diffraction (SAXS) w ere employed for LB film characterization on solid substrates. Paramet ers influencing the spreading and monolayer character include a) polar ity, b) balance of hydrophobicity to hydrophilicity, c) size and bulki ness of the polar groups attached to the fullerene, and d) presence of aromatic residues in these groups.