Matching Helical and Supramolecular Chirality in a Perylene Diimide Dimer: Impact on (Chir)Optical Properties

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Abstract Understanding the interplay between different forms of chirality in organic materials is critical for tuning and optimizing their (chir)optical properties. There is a growing interest in chiral chromophores such as bay-substituted perylene diimides (PDIs) due to their intrinsic helicity (M/P) which, at a higher level of organization, can also generate supramolecular chirality (Ms/Ps). The relationship between helical and supramolecular chirality governs interchromophore coupling, rotatory strengths, and subsequently circular dichroism (CD) and circularly polarized luminescence (CPL) spectra. Herein, we report the first PDI dimers that match helical and supramolecular chirality, e.g., PP–Ps. In agreement with theory, this chiral synergy contributes to enhanced CD and broadband CPL with high CPL brightness, properties of significant value for optical filtering in next-generation chiral sensors and displays.

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