Synthesis and Structural, Electrochemical, and Stacking Properties of Conical Molecules Possessing Buckyferrocene on the Apex

A series of conical molecules featuring a [60]fullerene/ferrocene hybrid and five aralkyl side chains (Fe[C60{C6H4-(OCO-C6H3-(OR)2-3,4)-4}5]Cp) have been synthesized and examined for their structural and electrochemical properties as well as their ability to form supramolecular structures in crystals and liquid crystals. When the R group on the side is a methyl group, the compound forms crystals in which the dipolar conical molecules are stacked head-to-tail to form a columnar structure. When the R group is as long as a C18H38 group, the compound forms liquid crystals. Oxidation of the liquid crystalline compound by an aminium salt [(4-BrC6H4)3N][SbCl6] produces the corresponding paramagnetic Fe(III) compound that also exhibits liquid crystalline properties.