Search for conglomerate in set of [7]helquat salts: multigram resolution of helicene-viologen hybrid by preferential crystallization.

Investigation of a set of 12 [7]helquat salts by X-ray crystal diffraction led to identification of conglomerate behavior in bis(trifluoroacetate) salt [2]CF(3)CO(2). This is to demonstrate that a systematic search for conglomerates can be performed for a given helicenoid enabling straightforward multigram resolution via preferential crystallization. Subsequently, preferential crystallization of this chiral helicene-viologen hybrid has been established to obtain pure P and M enantiomers on a multigram scale, 5 g each. Furthermore, preparation of nonracemic samples of [7]helquat 2 via diastereomeric (R,R)-dibenzoyltartrate salts is described, and determination of absolute configuration and racemization barrier is also reported.