Amphiphilic [5:1]‐ and [3:3]‐Hexakisadducts of C60

We have synthesized and characterized a variety of new amphiphilic hexakisadducts of C60 involving mixed octahedral [5:1]- and [3:3]-addition patterns. The [5:1]-adducts 3 and 13 contain five pairs of didodecyl or diethyl malonates as non-polar addends and, as their polar part, an extended bis(malonate) involving C14 and ethylene glycol chains and two biotin termini. For the first time, amphiphilic [3:3]-hexakisadducts have been prepared using the e,e,e-trisadduct 18, which contains a cyclo-[3]-octyl malonate addend, as the precursor. As polar groups, we used malonates featuring carboxy, amino, or peptide termini. The charge on the termini, which can range from zero up to sixfold positive or sixfold negative, can be built up by protonation or deprotonation. All the amphiphilic [3:3]-hexakisadducts are very soluble in water in their completely charged forms. Initial investigations on the aggregation properties of the amphiphilic [3:3]-hexakisadducts, conducted using transmission electron microscopy (TEM) and pulse-gradient spin echo (PGSE) NMR spectroscopy, reveal the pH-dependent formation of aggregates. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)