The structural properties of ten helicenebisquinones that have side chains differing innumber and structure are analyzed by means of polarized light microscopy, differentialthermal analysis, and X-ray diffraction. All the derivatives whose side chains are bonded tothe helical cores by ether linkages assemble into hexagonally arrayed columns, even whenthe number of side chains is only two, but not all form true liquid crystalline phases. Thosethat have three unsymmetrically disposed side chains do, and when these side chains aredodecyloxymethoxy groups, the clearing temperatures are as low as 107
C, which is 125
Clower than that of the only previously studied nonracemic helicenebisquinone. Differencesin side chain chirality affect the melting characteristics moderately, but they affect thepacking arrangements, as analyzed by X-ray diffraction, insignificantly. A set of models isproposed to account for the differences in the materials' properties.