Helical Growth of Semiconducting Columnar Dye Assemblies Based on Chiral Perylene Bisimides

A perylene bisimide derivative bearing two phenyl substituents with chiral solubilizing alkyl chains at the imide N atoms has been synthesized, and its self-assembly properties in solution and condensed phase have been investigated. Temperature-dependent CD spectra revealed the coexistence of two different kinds of chiral aggregates, differing in size and handedness. The chiral side chains effect a higher order within the self-assemblies, resulting in an increased charge-carrier mobility in the columnar liquid crystalline mesophase. [structure: see text]