Inversion of Supramolecular Chirality in Bichromophoric Perylene Bisimides: Influence of Temperature and Ultrasound

The supramolecular helicity in the self-assembled nanostructures of two perylene bisimide bichromophoric systems could be controlled by varying the preparatory methods. The self-assembly of the compounds under different conditions was investigated in detail by using absorption, fluorescence, CD, FTIR, XRD, TEM, and SEM techniques. These studies reveal that the heating–cooling method results in aggregates with ordered molecular packing and enhanced optical chirality. Ultrasonication leads to molecular aggregates with less ordered packing wherein the supramolecular chirality was reversed relative to the sample prepared via a heating–cooling method. This heating–cooling method proved to be superior in terms of nanofiber synthesis, yielding fibers with extended length and a prominent helical twist. At higher concentration, both compounds exhibited a gelation property in benzonitrile. The tunable chiroptical properties in these supramolecular systems make them potential candidates for applications in the field of optical and electronic device fabrication based on organic nanostructures.