Perylene bisimides (PBIs) are amongst the most studied colorants in supramolecular chemistry due to their unmatched combination of favorable optical and redox properties in the monomeric as well as self-assembled states. These features can be finely tuned by chemical modification of the monomeric building blocks. In this regard, we recently reported 1,6,7,12-tetraalkoxy- and 1,6,7,12-tetrahydroxy-substituted PBIs which were successfully applied in organic solar cells. Now we report on tetra-acyloxy functionalized PBIs which exhibit free NH groups in imide position for hydrogen bond-directed self-assembly. In our contribution we will show that this new modification enables the formation of two types of polymorphic dye aggregates with distinct optical and morphological features in solution as well as the solid state. The contrasting self-assembly behavior is achieved by adjusting the cooling rate applied to a hot solution of monomers in a non-polar solvent (Figure 1). Our further studies are directed towards deriving structure-function relationships for these aggregates and applying them as materials for organic electronics and photovoltaics.

Supramolecular polymorphism in aggregates of tetra-bay-acyloxy functionalized perylene bisimides

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.